Your Next Adventure
Your Next Adventure
Cape Cod & Martha's Vineyard Bike Tour
DURATION
6 Day(s)
DAILY BIKING
28 Miles
TRIP DIFFICULTY
2-Easier to Intermediate
REVIEWS
STARTING FROM
$3295
SINGLES ADD FROM
$900
Trip Overview
On this bike tour, you stay three nights at the newly renovated Harbor View Hotel in Edgartown, Massachusetts, where your premier room is in the historic main building.
This tour has everything! On the Cape you follow beach roads and a beautiful bike path as you weave your way past salt marshes, cranberry bogs, bird sanctuaries, barrier beaches and tidal flats filled with egrets, geese and ducks.
A scenic ferry ride takes you to Martha’s Vineyard and elegant Edgartown, a colonial seaport with rows of handsome 18th-century homes. Cycle to Katama with its beautiful barrier beach, and to historic West Tisbury. Plus, visit Vineyard Haven, ride past historic West Chop Light and ride “up island” to the spectacular lookout at Aquinnah Cliffs. Enjoy a picnic at a sculpture garden and visit the picturesque village of Menemsha, where we bike down to the harbor and stroll along the beach. From near the hotel, there's a 2-minute ferry ride to Chappaquiddick. And don't miss cycling along a beautiful bike path to Oak Bluffs. Here we explore famous labyrinthine streets lined with fanciful rainbow-colored gingerbread cottages and visit the town’s antique Flying Horses Carousel before returning to the inn.
Our two inns are the best! On the Cape you stay at the charming Palmer House Inn perfectly situated in the tree-lined historic district of Falmouth. And in Edgartown, you enjoy the wonderful rooms at the Harbor View Hotel where you can look out past the Edgartown Lighthouse and Chappaquiddick Island. From here, you can enjoy walking the narrow streets of this former whaling seaport with its handsome 18th-century houses and white picket fences, as well as high-end boutiques and art galleries.
Itinerary
From start to finish, check out the route.
DAY 1 - Welcome to Cape Cod!
Arrival day | Palmer House Inn
Sunday we are welcomed to Cape Cod by the innkeepers at the Palmer House Inn in Falmouth. The inn is a delightful Victorian property perfectly situated in the tree lined historic district … and only a 4-minute walk from all the wonderful shops, galleries and restaurants of Falmouth. In the evening we gather for the short stroll to one of the area’s finest restaurants followed by a friendly get together in the common areas of the inn.
Sunday we are welcomed to Cape Cod by the innkeepers at the Palmer House Inn in Falmouth. The inn is a delightful Victorian property perfectly situated in the tree lined historic district … and only a 4-minute walk from all the wonderful shops, galleries and restaurants of Falmouth. In the evening we gather for the short stroll to one of the area’s finest restaurants followed by a friendly get together in the common areas of the inn.
DAY 2 - Shining Sea Bike Path
Distance: 24 or 34 miles | Terrain: Easier | Palmer House Inn
Monday’s ride is spectacular. Part of the day we follow the famous Shining Sea Bikeway as we weave our way past salt marshes, cranberry bogs, bird sanctuaries, beaches and harbors. We follow some quiet roads to the shores of Vineyard Sound in Falmouth, and then follow Surf Drive and Beach Road past Little Pond and Inner Harbor where hundreds of yachts and sailboats sway at anchor. We skirt past Oyster Pond and can pause here to breathe in the sea air or watch osprey and heron or take a brief side trip to Spohr Gardens where we are treated to an array of over 100,000 daffodils, lilies, magnolias and azaleas.
Monday’s ride is spectacular. Part of the day we follow the famous Shining Sea Bikeway as we weave our way past salt marshes, cranberry bogs, bird sanctuaries, beaches and harbors. We follow some quiet roads to the shores of Vineyard Sound in Falmouth, and then follow Surf Drive and Beach Road past Little Pond and Inner Harbor where hundreds of yachts and sailboats sway at anchor. We skirt past Oyster Pond and can pause here to breathe in the sea air or watch osprey and heron or take a brief side trip to Spohr Gardens where we are treated to an array of over 100,000 daffodils, lilies, magnolias and azaleas.
DAY 3 - Martha’s Vineyard
Distance: 30 or 40 miles | Terrain: Easier | Harbor View Hotel
After a superb breakfast, you ride back into Woods Hole to start our ferry ride together to Martha’s Vineyard. This is a delightful transition from mainland to island and includes gorgeous views of the harbor and Vineyard Sound. You arrive 45 minutes later in Vineyard Haven. Ride from there along a lovely route (that includes a seaside bike path) to the easterly end of the island. Streets lined with handsome 18th-Century houses surrounded by white picket fences and topped with widow walks announce that you have arrived in Edgartown, a world-renowned seaport that still reflects the wealth and good taste of the phenomenally successful whaler captains of the early 1800’s.
Now’s a great time for a short stroll and lunch. If the rooms are not ready yet, then cycle to a 2-minute ferry crossing to Chappaquiddick for a spin. You return via the short ferry to Edgartown to check in at the elegant Harbor View Hotel — your home for the next three nights — just a few minutes’ walk from all the boutique shops and waterfront galleries for which Edgartown is so rightfully famous. Dinner is on your own in Edgartown tonight.
After a superb breakfast, you ride back into Woods Hole to start our ferry ride together to Martha’s Vineyard. This is a delightful transition from mainland to island and includes gorgeous views of the harbor and Vineyard Sound. You arrive 45 minutes later in Vineyard Haven. Ride from there along a lovely route (that includes a seaside bike path) to the easterly end of the island. Streets lined with handsome 18th-Century houses surrounded by white picket fences and topped with widow walks announce that you have arrived in Edgartown, a world-renowned seaport that still reflects the wealth and good taste of the phenomenally successful whaler captains of the early 1800’s.
Now’s a great time for a short stroll and lunch. If the rooms are not ready yet, then cycle to a 2-minute ferry crossing to Chappaquiddick for a spin. You return via the short ferry to Edgartown to check in at the elegant Harbor View Hotel — your home for the next three nights — just a few minutes’ walk from all the boutique shops and waterfront galleries for which Edgartown is so rightfully famous. Dinner is on your own in Edgartown tonight.
DAY 4 - Views, village & sculpture garden
Distance: 23 or 38 miles | Terrain: Easier to Intermediate | Harbor View Hotel
Today’s ride first takes you to Menemsha, a supremely picturesque fishing village situated on Menemsha Pond and Vineyard Sound. This historic harbor serves as the point of departure for most of the local fishermen and is usually bustling with activity. Then head through quaint and quiet villages that evoke the island’s maritime past. Fuel your ride and indulge your artistic side with a picnic lunch at the Field Gallery and Sculpture Garden.
Then ride out to Aquinnah Cliffs (formerly Gay Head), one of the most spectacular spots on the island. After enjoying the multi-mile views from the lookout, you take the boardwalk to the beach so as to better see the mosaic of colors for which the cliffs are rightfully famous. You might also stop at the top of the cliffs to visit the several interesting shops owned by the indigenous Wampanoag Indians.
Today’s ride first takes you to Menemsha, a supremely picturesque fishing village situated on Menemsha Pond and Vineyard Sound. This historic harbor serves as the point of departure for most of the local fishermen and is usually bustling with activity. Then head through quaint and quiet villages that evoke the island’s maritime past. Fuel your ride and indulge your artistic side with a picnic lunch at the Field Gallery and Sculpture Garden.
Then ride out to Aquinnah Cliffs (formerly Gay Head), one of the most spectacular spots on the island. After enjoying the multi-mile views from the lookout, you take the boardwalk to the beach so as to better see the mosaic of colors for which the cliffs are rightfully famous. You might also stop at the top of the cliffs to visit the several interesting shops owned by the indigenous Wampanoag Indians.
DAY 5 - Artists, galleries & cottages
Distance: 26 or 40 miles | Terrain: Easier to Intermediate | Harbor View Hotel
Follow bike paths to West Tisbury, home to a number of Vineyard artists, and galleries, and to Alley’s, a quintessential New England general store. You then weave your way past Lambert’s Cove and take back roads into Vineyard Haven where you visit the handsome West Chop Lighthouse with its great view over Vineyard Sound. Here you might also enjoy the numerous small shops in the village and maybe stop for refreshments at the iconic Black Dog Tavern.
Then cycle along a beautiful bike path to Oak Bluffs. Here you explore famous labyrinthine streets lined with fanciful rainbow-colored gingerbread cottages and visit the town’s antique Flying Horses Carousel. You may also want to splurge at one of the local ice cream emporiums before finishing the day’s ride along the Beach Road bike path as it cuts its way between the ocean on one side and beautiful salt marshes on the other. You end your ride in Edgartown to get ready for our celebratory last evening together.
Follow bike paths to West Tisbury, home to a number of Vineyard artists, and galleries, and to Alley’s, a quintessential New England general store. You then weave your way past Lambert’s Cove and take back roads into Vineyard Haven where you visit the handsome West Chop Lighthouse with its great view over Vineyard Sound. Here you might also enjoy the numerous small shops in the village and maybe stop for refreshments at the iconic Black Dog Tavern.
Then cycle along a beautiful bike path to Oak Bluffs. Here you explore famous labyrinthine streets lined with fanciful rainbow-colored gingerbread cottages and visit the town’s antique Flying Horses Carousel. You may also want to splurge at one of the local ice cream emporiums before finishing the day’s ride along the Beach Road bike path as it cuts its way between the ocean on one side and beautiful salt marshes on the other. You end your ride in Edgartown to get ready for our celebratory last evening together.
DAY 6 - Departure Day
Distance: 17 miles | Terrain: Easier
On Friday you can opt for an early morning ferry ride to Chappaquiddick before cycling along a beautiful bike path to Oak Bluffs. Here we explore famous labyrinthine streets lined with fanciful rainbow-colored gingerbread cottages and visit the town’s antique Flying Horses Carousel. You may also want to splurge at one of the local ice cream emporiums before finishing the day’s ride along the Beach Road bike path as it cuts its way between the ocean on one side and beautiful salt marshes on the other. You end your tour with a ride on the ferry back to Woods Hole and a shuttle to the Palmer House Inn.
On Friday you can opt for an early morning ferry ride to Chappaquiddick before cycling along a beautiful bike path to Oak Bluffs. Here we explore famous labyrinthine streets lined with fanciful rainbow-colored gingerbread cottages and visit the town’s antique Flying Horses Carousel. You may also want to splurge at one of the local ice cream emporiums before finishing the day’s ride along the Beach Road bike path as it cuts its way between the ocean on one side and beautiful salt marshes on the other. You end your tour with a ride on the ferry back to Woods Hole and a shuttle to the Palmer House Inn.
Itinerary
From start to finish, check out the route.
DAY 1 - Welcome to Cape Cod!
Arrival day | Palmer House Inn
Sunday we are welcomed to Cape Cod by the innkeepers at the Palmer House Inn in Falmouth. The inn is a delightful Victorian property perfectly situated in the tree lined historic district … and only a 4-minute walk from all the wonderful shops, galleries and restaurants of Falmouth. In the evening we gather for the short stroll to one of the area’s finest restaurants followed by a friendly get together in the common areas of the inn.
Sunday we are welcomed to Cape Cod by the innkeepers at the Palmer House Inn in Falmouth. The inn is a delightful Victorian property perfectly situated in the tree lined historic district … and only a 4-minute walk from all the wonderful shops, galleries and restaurants of Falmouth. In the evening we gather for the short stroll to one of the area’s finest restaurants followed by a friendly get together in the common areas of the inn.
DAY 2 - Shining Sea Bike Path
Distance: 24 or 34 miles | Terrain: Easier | Palmer House Inn
Monday’s ride is spectacular. Part of the day we follow the famous Shining Sea Bikeway as we weave our way past salt marshes, cranberry bogs, bird sanctuaries, beaches and harbors. We follow some quiet roads to the shores of Vineyard Sound in Falmouth, and then follow Surf Drive and Beach Road past Little Pond and Inner Harbor where hundreds of yachts and sailboats sway at anchor. We skirt past Oyster Pond and can pause here to breathe in the sea air or watch osprey and heron or take a brief side trip to Spohr Gardens where we are treated to an array of over 100,000 daffodils, lilies, magnolias and azaleas.
Monday’s ride is spectacular. Part of the day we follow the famous Shining Sea Bikeway as we weave our way past salt marshes, cranberry bogs, bird sanctuaries, beaches and harbors. We follow some quiet roads to the shores of Vineyard Sound in Falmouth, and then follow Surf Drive and Beach Road past Little Pond and Inner Harbor where hundreds of yachts and sailboats sway at anchor. We skirt past Oyster Pond and can pause here to breathe in the sea air or watch osprey and heron or take a brief side trip to Spohr Gardens where we are treated to an array of over 100,000 daffodils, lilies, magnolias and azaleas.
DAY 3 - Martha’s Vineyard
Distance: 30 or 40 miles | Terrain: Easier | Harbor View Hotel
After a superb breakfast, we ride back into Woods Hole to start our ferry ride to Martha’s Vineyard. This is a delightful transition from mainland to island and includes gorgeous views of the harbor and Vineyard Sound. We arrive 45 minutes later in Vineyard Haven and ride from there along a lovely route (that includes a sea side bike path) to the easterly end of the island. Streets lined with handsome Eighteenth Century houses surrounded by white picket fences and topped with widow walks announce that you have arrived in Edgartown, a world-renowned seaport that still reflects the wealth and good taste of the phenomenally successful whaler captains of the early 1800’s. Our home is here for the next three nights where we are guests at the prestigious Harbor View Hotel located near the Chappaquiddick Ferry landing and just a few minute’s walk from all the boutique shops and waterfront galleries for which Edgartown is so rightfully famous.
After a superb breakfast, we ride back into Woods Hole to start our ferry ride to Martha’s Vineyard. This is a delightful transition from mainland to island and includes gorgeous views of the harbor and Vineyard Sound. We arrive 45 minutes later in Vineyard Haven and ride from there along a lovely route (that includes a sea side bike path) to the easterly end of the island. Streets lined with handsome Eighteenth Century houses surrounded by white picket fences and topped with widow walks announce that you have arrived in Edgartown, a world-renowned seaport that still reflects the wealth and good taste of the phenomenally successful whaler captains of the early 1800’s. Our home is here for the next three nights where we are guests at the prestigious Harbor View Hotel located near the Chappaquiddick Ferry landing and just a few minute’s walk from all the boutique shops and waterfront galleries for which Edgartown is so rightfully famous.
DAY 4 - Vineyard, artists, and galleries
Distance: 23 or 38 miles | Terrain: Easier to Intermediate | Harbor View Hotel
Wednesday’s ride first takes us to Katama where we can warm our feet in the sand on the beautiful three-mile barrier beach, then follow bike paths to West Tisbury, home to a number of Vineyard artists, and galleries, and to Alley’s, a quintessential general store. We then weave our way past Lambert’s Cove and take back roads into Vineyard Haven where we visit the handsome West Chop Lighthouse with its great view over Vineyard Sound. Here we might also enjoy the numerous small shops in the village and maybe stop for refreshments at the iconic Black Dog Tavern. In the evenings we have plenty of time to explore Edgartown. Edgartown is a great place to walk and, if you are in the mood, a great place to shop as well. Most stores are boutiques for high end apparel, jewelry, etc. but arts and antiques are also represented. Rounding out the selection are the requisite T-shirt and souvenir shops and you will want to indulge in the time-honored tradition of sampling the fudge and brittle at Murdick’s.
Wednesday’s ride first takes us to Katama where we can warm our feet in the sand on the beautiful three-mile barrier beach, then follow bike paths to West Tisbury, home to a number of Vineyard artists, and galleries, and to Alley’s, a quintessential general store. We then weave our way past Lambert’s Cove and take back roads into Vineyard Haven where we visit the handsome West Chop Lighthouse with its great view over Vineyard Sound. Here we might also enjoy the numerous small shops in the village and maybe stop for refreshments at the iconic Black Dog Tavern. In the evenings we have plenty of time to explore Edgartown. Edgartown is a great place to walk and, if you are in the mood, a great place to shop as well. Most stores are boutiques for high end apparel, jewelry, etc. but arts and antiques are also represented. Rounding out the selection are the requisite T-shirt and souvenir shops and you will want to indulge in the time-honored tradition of sampling the fudge and brittle at Murdick’s.
DAY 5 - Quaint and quiet villages
Distance: 26 or 40 miles | Terrain: Easier to Intermediate | Harbor View Hotel
Thursday’s ride takes us “up island” through quaint and quiet villages that evoke the island’s maritime past. We ride out to Aquinnah Cliffs (formerly Gay Head), one of the most spectacular spots on the island. After enjoying the multi-mile views from the lookout we will take the boardwalk to the beach so as to better see the mosaic of colors for which the cliffs are rightfully famous. We might also stop at the top of the cliffs to visit the several interesting shops owned by the indigenous Wampanoag Indians. On your way back from Aquinnah we will stop in the fishing village of Menemsha, a supremely picturesque fishing village situated on Menemsha Pond and Vineyard Sound. This historic harbor serves as the point of departure for most of the local fishermen, and is usually bustling with activity. We will also plan to picnic here, perhaps after a scenic walk along beautiful Menemsha Beach.
Thursday’s ride takes us “up island” through quaint and quiet villages that evoke the island’s maritime past. We ride out to Aquinnah Cliffs (formerly Gay Head), one of the most spectacular spots on the island. After enjoying the multi-mile views from the lookout we will take the boardwalk to the beach so as to better see the mosaic of colors for which the cliffs are rightfully famous. We might also stop at the top of the cliffs to visit the several interesting shops owned by the indigenous Wampanoag Indians. On your way back from Aquinnah we will stop in the fishing village of Menemsha, a supremely picturesque fishing village situated on Menemsha Pond and Vineyard Sound. This historic harbor serves as the point of departure for most of the local fishermen, and is usually bustling with activity. We will also plan to picnic here, perhaps after a scenic walk along beautiful Menemsha Beach.
DAY 6 - Departure Day
Distance: 17 miles | Terrain: Easier
On Friday you can opt for an early morning ferry ride to Chappaquiddick before cycling along a beautiful bike path to Oak Bluffs. Here we explore famous labyrinthine streets lined with fanciful rainbow-colored gingerbread cottages and visit the town’s antique Flying Horses Carousel. You may also want to splurge at one of the local ice cream emporiums before finishing the day’s ride along the Beach Road bike path as it cuts its way between the ocean on one side and beautiful salt marshes on the other. You end your tour with a ride on the ferry back to Woods Hole and a shuttle to the Palmer House Inn.
On Friday you can opt for an early morning ferry ride to Chappaquiddick before cycling along a beautiful bike path to Oak Bluffs. Here we explore famous labyrinthine streets lined with fanciful rainbow-colored gingerbread cottages and visit the town’s antique Flying Horses Carousel. You may also want to splurge at one of the local ice cream emporiums before finishing the day’s ride along the Beach Road bike path as it cuts its way between the ocean on one side and beautiful salt marshes on the other. You end your tour with a ride on the ferry back to Woods Hole and a shuttle to the Palmer House Inn.
Itinerary
From start to finish, check out the route.
DAY 1 - Welcome to Cape Cod!
Arrival day | Palmer House Inn
Sunday we are welcomed to Cape Cod by the innkeepers at the Palmer House Inn in Falmouth. The inn is a delightful Victorian property perfectly situated in the tree lined historic district … and only a 4-minute walk from all the wonderful shops, galleries and restaurants of Falmouth. In the evening we gather for the short stroll to one of the area’s finest restaurants followed by a friendly get together in the common areas of the inn.
Sunday we are welcomed to Cape Cod by the innkeepers at the Palmer House Inn in Falmouth. The inn is a delightful Victorian property perfectly situated in the tree lined historic district … and only a 4-minute walk from all the wonderful shops, galleries and restaurants of Falmouth. In the evening we gather for the short stroll to one of the area’s finest restaurants followed by a friendly get together in the common areas of the inn.
DAY 2 - Shining Sea Bike Path
Distance: 24 or 34 miles | Terrain: Easier | Palmer House Inn
Monday’s ride is spectacular. Part of the day we follow the famous Shining Sea Bikeway as we weave our way past salt marshes, cranberry bogs, bird sanctuaries, beaches and harbors. We follow some quiet roads to the shores of Vineyard Sound in Falmouth, and then follow Surf Drive and Beach Road past Little Pond and Inner Harbor where hundreds of yachts and sailboats sway at anchor. We skirt past Oyster Pond and can pause here to breathe in the sea air or watch osprey and heron or take a brief side trip to Spohr Gardens where we are treated to an array of over 100,000 daffodils, lilies, magnolias and azaleas.
Monday’s ride is spectacular. Part of the day we follow the famous Shining Sea Bikeway as we weave our way past salt marshes, cranberry bogs, bird sanctuaries, beaches and harbors. We follow some quiet roads to the shores of Vineyard Sound in Falmouth, and then follow Surf Drive and Beach Road past Little Pond and Inner Harbor where hundreds of yachts and sailboats sway at anchor. We skirt past Oyster Pond and can pause here to breathe in the sea air or watch osprey and heron or take a brief side trip to Spohr Gardens where we are treated to an array of over 100,000 daffodils, lilies, magnolias and azaleas.
DAY 3 - Martha’s Vineyard
Distance: 30 or 40 miles | Terrain: Easier | Harbor View Hotel
After a superb breakfast, we ride back into Woods Hole to start our ferry ride to Martha’s Vineyard. This is a delightful transition from mainland to island and includes gorgeous views of the harbor and Vineyard Sound. We arrive 45 minutes later in Vineyard Haven and ride from there along a lovely route (that includes a sea side bike path) to the easterly end of the island. Streets lined with handsome Eighteenth Century houses surrounded by white picket fences and topped with widow walks announce that you have arrived in Edgartown, a world-renowned seaport that still reflects the wealth and good taste of the phenomenally successful whaler captains of the early 1800’s. Our home is here for the next three nights where we are guests at the prestigious Harbor View Hotel located near the Chappaquiddick Ferry landing and just a few minute’s walk from all the boutique shops and waterfront galleries for which Edgartown is so rightfully famous.
After a superb breakfast, we ride back into Woods Hole to start our ferry ride to Martha’s Vineyard. This is a delightful transition from mainland to island and includes gorgeous views of the harbor and Vineyard Sound. We arrive 45 minutes later in Vineyard Haven and ride from there along a lovely route (that includes a sea side bike path) to the easterly end of the island. Streets lined with handsome Eighteenth Century houses surrounded by white picket fences and topped with widow walks announce that you have arrived in Edgartown, a world-renowned seaport that still reflects the wealth and good taste of the phenomenally successful whaler captains of the early 1800’s. Our home is here for the next three nights where we are guests at the prestigious Harbor View Hotel located near the Chappaquiddick Ferry landing and just a few minute’s walk from all the boutique shops and waterfront galleries for which Edgartown is so rightfully famous.
DAY 4 - Vineyard, artists, and galleries
Distance: 23 or 38 miles | Terrain: Easier to Intermediate | Harbor View Hotel
Wednesday’s ride first takes us to Katama where we can warm our feet in the sand on the beautiful three-mile barrier beach, then follow bike paths to West Tisbury, home to a number of Vineyard artists, and galleries, and to Alley’s, a quintessential general store. We then weave our way past Lambert’s Cove and take back roads into Vineyard Haven where we visit the handsome West Chop Lighthouse with its great view over Vineyard Sound. Here we might also enjoy the numerous small shops in the village and maybe stop for refreshments at the iconic Black Dog Tavern. In the evenings we have plenty of time to explore Edgartown. Edgartown is a great place to walk and, if you are in the mood, a great place to shop as well. Most stores are boutiques for high end apparel, jewelry, etc. but arts and antiques are also represented. Rounding out the selection are the requisite T-shirt and souvenir shops and you will want to indulge in the time-honored tradition of sampling the fudge and brittle at Murdick’s.
Wednesday’s ride first takes us to Katama where we can warm our feet in the sand on the beautiful three-mile barrier beach, then follow bike paths to West Tisbury, home to a number of Vineyard artists, and galleries, and to Alley’s, a quintessential general store. We then weave our way past Lambert’s Cove and take back roads into Vineyard Haven where we visit the handsome West Chop Lighthouse with its great view over Vineyard Sound. Here we might also enjoy the numerous small shops in the village and maybe stop for refreshments at the iconic Black Dog Tavern. In the evenings we have plenty of time to explore Edgartown. Edgartown is a great place to walk and, if you are in the mood, a great place to shop as well. Most stores are boutiques for high end apparel, jewelry, etc. but arts and antiques are also represented. Rounding out the selection are the requisite T-shirt and souvenir shops and you will want to indulge in the time-honored tradition of sampling the fudge and brittle at Murdick’s.
DAY 5 - Quaint and quiet villages
Distance: 26 or 40 miles | Terrain: Easier to Intermediate | Harbor View Hotel
Thursday’s ride takes us “up island” through quaint and quiet villages that evoke the island’s maritime past. We ride out to Aquinnah Cliffs (formerly Gay Head), one of the most spectacular spots on the island. After enjoying the multi-mile views from the lookout we will take the boardwalk to the beach so as to better see the mosaic of colors for which the cliffs are rightfully famous. We might also stop at the top of the cliffs to visit the several interesting shops owned by the indigenous Wampanoag Indians. On your way back from Aquinnah we will stop in the fishing village of Menemsha, a supremely picturesque fishing village situated on Menemsha Pond and Vineyard Sound. This historic harbor serves as the point of departure for most of the local fishermen, and is usually bustling with activity. We will also plan to picnic here, perhaps after a scenic walk along beautiful Menemsha Beach.
Thursday’s ride takes us “up island” through quaint and quiet villages that evoke the island’s maritime past. We ride out to Aquinnah Cliffs (formerly Gay Head), one of the most spectacular spots on the island. After enjoying the multi-mile views from the lookout we will take the boardwalk to the beach so as to better see the mosaic of colors for which the cliffs are rightfully famous. We might also stop at the top of the cliffs to visit the several interesting shops owned by the indigenous Wampanoag Indians. On your way back from Aquinnah we will stop in the fishing village of Menemsha, a supremely picturesque fishing village situated on Menemsha Pond and Vineyard Sound. This historic harbor serves as the point of departure for most of the local fishermen, and is usually bustling with activity. We will also plan to picnic here, perhaps after a scenic walk along beautiful Menemsha Beach.
DAY 6 - Departure Day
Distance: 17 miles | Terrain: Easier
On Friday you can opt for an early morning ferry ride to Chappaquiddick before cycling along a beautiful bike path to Oak Bluffs. Here we explore famous labyrinthine streets lined with fanciful rainbow-colored gingerbread cottages and visit the town’s antique Flying Horses Carousel. You may also want to splurge at one of the local ice cream emporiums before finishing the day’s ride along the Beach Road bike path as it cuts its way between the ocean on one side and beautiful salt marshes on the other. You end your tour with a ride on the ferry back to Woods Hole and a shuttle to the Palmer House Inn.
On Friday you can opt for an early morning ferry ride to Chappaquiddick before cycling along a beautiful bike path to Oak Bluffs. Here we explore famous labyrinthine streets lined with fanciful rainbow-colored gingerbread cottages and visit the town’s antique Flying Horses Carousel. You may also want to splurge at one of the local ice cream emporiums before finishing the day’s ride along the Beach Road bike path as it cuts its way between the ocean on one side and beautiful salt marshes on the other. You end your tour with a ride on the ferry back to Woods Hole and a shuttle to the Palmer House Inn.
Itinerary
From start to finish, check out the route.
DAY 1 - Welcome to Cape Cod!
Arrival day | Palmer House Inn
Sunday we are welcomed to Cape Cod by the innkeepers at the Palmer House Inn in Falmouth. The inn is a delightful Victorian property perfectly situated in the tree lined historic district … and only a 4-minute walk from all the wonderful shops, galleries and restaurants of Falmouth. In the evening we gather for the short stroll to one of the area’s finest restaurants followed by a friendly get together in the common areas of the inn.
Sunday we are welcomed to Cape Cod by the innkeepers at the Palmer House Inn in Falmouth. The inn is a delightful Victorian property perfectly situated in the tree lined historic district … and only a 4-minute walk from all the wonderful shops, galleries and restaurants of Falmouth. In the evening we gather for the short stroll to one of the area’s finest restaurants followed by a friendly get together in the common areas of the inn.
DAY 2 - Shining Sea Bike Path
Distance: 24 or 34 miles | Terrain: Easier | Palmer House Inn
Monday’s ride is spectacular. Part of the day we follow the famous Shining Sea Bikeway as we weave our way past salt marshes, cranberry bogs, bird sanctuaries, beaches and harbors. We follow some quiet roads to the shores of Vineyard Sound in Falmouth, and then follow Surf Drive and Beach Road past Little Pond and Inner Harbor where hundreds of yachts and sailboats sway at anchor. We skirt past Oyster Pond and can pause here to breathe in the sea air or watch osprey and heron or take a brief side trip to Spohr Gardens where we are treated to an array of over 100,000 daffodils, lilies, magnolias and azaleas.
Monday’s ride is spectacular. Part of the day we follow the famous Shining Sea Bikeway as we weave our way past salt marshes, cranberry bogs, bird sanctuaries, beaches and harbors. We follow some quiet roads to the shores of Vineyard Sound in Falmouth, and then follow Surf Drive and Beach Road past Little Pond and Inner Harbor where hundreds of yachts and sailboats sway at anchor. We skirt past Oyster Pond and can pause here to breathe in the sea air or watch osprey and heron or take a brief side trip to Spohr Gardens where we are treated to an array of over 100,000 daffodils, lilies, magnolias and azaleas.
DAY 3 - Martha’s Vineyard
Distance: 30 or 40 miles | Terrain: Easier | Harbor View Hotel
After a superb breakfast, we ride back into Woods Hole to start our ferry ride to Martha’s Vineyard. This is a delightful transition from mainland to island and includes gorgeous views of the harbor and Vineyard Sound. We arrive 45 minutes later in Vineyard Haven and ride from there along a lovely route (that includes a sea side bike path) to the easterly end of the island. Streets lined with handsome Eighteenth Century houses surrounded by white picket fences and topped with widow walks announce that you have arrived in Edgartown, a world-renowned seaport that still reflects the wealth and good taste of the phenomenally successful whaler captains of the early 1800’s. Our home is here for the next three nights where we are guests at the prestigious Harbor View Hotel located near the Chappaquiddick Ferry landing and just a few minute’s walk from all the boutique shops and waterfront galleries for which Edgartown is so rightfully famous.
After a superb breakfast, we ride back into Woods Hole to start our ferry ride to Martha’s Vineyard. This is a delightful transition from mainland to island and includes gorgeous views of the harbor and Vineyard Sound. We arrive 45 minutes later in Vineyard Haven and ride from there along a lovely route (that includes a sea side bike path) to the easterly end of the island. Streets lined with handsome Eighteenth Century houses surrounded by white picket fences and topped with widow walks announce that you have arrived in Edgartown, a world-renowned seaport that still reflects the wealth and good taste of the phenomenally successful whaler captains of the early 1800’s. Our home is here for the next three nights where we are guests at the prestigious Harbor View Hotel located near the Chappaquiddick Ferry landing and just a few minute’s walk from all the boutique shops and waterfront galleries for which Edgartown is so rightfully famous.
DAY 4 - Vineyard, artists, and galleries
Distance: 23 or 38 miles | Terrain: Easier to Intermediate | Harbor View Hotel
Wednesday’s ride first takes us to Katama where we can warm our feet in the sand on the beautiful three-mile barrier beach, then follow bike paths to West Tisbury, home to a number of Vineyard artists, and galleries, and to Alley’s, a quintessential general store. We then weave our way past Lambert’s Cove and take back roads into Vineyard Haven where we visit the handsome West Chop Lighthouse with its great view over Vineyard Sound. Here we might also enjoy the numerous small shops in the village and maybe stop for refreshments at the iconic Black Dog Tavern. In the evenings we have plenty of time to explore Edgartown. Edgartown is a great place to walk and, if you are in the mood, a great place to shop as well. Most stores are boutiques for high end apparel, jewelry, etc. but arts and antiques are also represented. Rounding out the selection are the requisite T-shirt and souvenir shops and you will want to indulge in the time-honored tradition of sampling the fudge and brittle at Murdick’s.
Wednesday’s ride first takes us to Katama where we can warm our feet in the sand on the beautiful three-mile barrier beach, then follow bike paths to West Tisbury, home to a number of Vineyard artists, and galleries, and to Alley’s, a quintessential general store. We then weave our way past Lambert’s Cove and take back roads into Vineyard Haven where we visit the handsome West Chop Lighthouse with its great view over Vineyard Sound. Here we might also enjoy the numerous small shops in the village and maybe stop for refreshments at the iconic Black Dog Tavern. In the evenings we have plenty of time to explore Edgartown. Edgartown is a great place to walk and, if you are in the mood, a great place to shop as well. Most stores are boutiques for high end apparel, jewelry, etc. but arts and antiques are also represented. Rounding out the selection are the requisite T-shirt and souvenir shops and you will want to indulge in the time-honored tradition of sampling the fudge and brittle at Murdick’s.
DAY 5 - Quaint and quiet villages
Distance: 26 or 40 miles | Terrain: Easier to Intermediate | Harbor View Hotel
Thursday’s ride takes us “up island” through quaint and quiet villages that evoke the island’s maritime past. We ride out to Aquinnah Cliffs (formerly Gay Head), one of the most spectacular spots on the island. After enjoying the multi-mile views from the lookout we will take the boardwalk to the beach so as to better see the mosaic of colors for which the cliffs are rightfully famous. We might also stop at the top of the cliffs to visit the several interesting shops owned by the indigenous Wampanoag Indians. On your way back from Aquinnah we will stop in the fishing village of Menemsha, a supremely picturesque fishing village situated on Menemsha Pond and Vineyard Sound. This historic harbor serves as the point of departure for most of the local fishermen, and is usually bustling with activity. We will also plan to picnic here, perhaps after a scenic walk along beautiful Menemsha Beach.
Thursday’s ride takes us “up island” through quaint and quiet villages that evoke the island’s maritime past. We ride out to Aquinnah Cliffs (formerly Gay Head), one of the most spectacular spots on the island. After enjoying the multi-mile views from the lookout we will take the boardwalk to the beach so as to better see the mosaic of colors for which the cliffs are rightfully famous. We might also stop at the top of the cliffs to visit the several interesting shops owned by the indigenous Wampanoag Indians. On your way back from Aquinnah we will stop in the fishing village of Menemsha, a supremely picturesque fishing village situated on Menemsha Pond and Vineyard Sound. This historic harbor serves as the point of departure for most of the local fishermen, and is usually bustling with activity. We will also plan to picnic here, perhaps after a scenic walk along beautiful Menemsha Beach.
DAY 6 - Departure Day
Distance: 17 miles | Terrain: Easier
On Friday you can opt for an early morning ferry ride to Chappaquiddick before cycling along a beautiful bike path to Oak Bluffs. Here we explore famous labyrinthine streets lined with fanciful rainbow-colored gingerbread cottages and visit the town’s antique Flying Horses Carousel. You may also want to splurge at one of the local ice cream emporiums before finishing the day’s ride along the Beach Road bike path as it cuts its way between the ocean on one side and beautiful salt marshes on the other. You end your tour with a ride on the ferry back to Woods Hole and a shuttle to the Palmer House Inn.
On Friday you can opt for an early morning ferry ride to Chappaquiddick before cycling along a beautiful bike path to Oak Bluffs. Here we explore famous labyrinthine streets lined with fanciful rainbow-colored gingerbread cottages and visit the town’s antique Flying Horses Carousel. You may also want to splurge at one of the local ice cream emporiums before finishing the day’s ride along the Beach Road bike path as it cuts its way between the ocean on one side and beautiful salt marshes on the other. You end your tour with a ride on the ferry back to Woods Hole and a shuttle to the Palmer House Inn.
Map
Dates & Pricing
Prices are per person based on double occupancy (2 people in one room). Single supplement for private room is listed at the top of this page. A deposit of $500 holds your reservation for most tours. For weekend tours, the deposit is $300.
What’s Included
Round trip ferry to Martha’s Vineyard and the ferry to Chappaquiddick, 5 nights 'lodging, 3 dinners (you are on your own for dinner 2 nights in Edgartown), 5 breakfasts, a picnic, use of a bicycle and helmet. Free transfer provided from/to Falmouth bus station at the start of the tour. Arrival: 5:30 PM pickup at Falmouth Bus Station. Airfare and car parking at ferry not included.
Dates & Pricing
Prices are per person based on double occupancy (2 people in one room). Single supplement for private room is listed at the top of this page. A deposit of $500 holds your reservation for most tours. For weekend tours, the deposit is $300.
What’s Included
Round trip ferry to Martha’s Vineyard and the ferry to Chappaquiddick, 5 nights 'lodging, 3 dinners (you are on your own for dinner 2 nights in Edgartown), 5 breakfasts, a picnic, use of a bicycle and helmet. Free transfer provided from/to Falmouth bus station at the start of the tour. Arrival: 5:30 PM pickup at Falmouth Bus Station. Airfare and car parking at ferry not included.
Inns
Where you stay along the way.
Palmer House Inn
A charming bed and breakfast located in Falmouth, Massachusetts. Falmouth is a delightful New England village on Upper Cape Cod. Our romantic bed and breakfast is located in the Historic District, a quiet residential area of tree-lined streets, picket fences, colorful gardens, and elegant homes all decorated for the holidays. Beautiful beaches, quaint shops, ferry shuttles and excellent restaurants, are only a short stroll from our Cape Cod Bed and Breakfast.
Harbor View Hotel
Built in 1891, overlooking Martha’s Vineyard’s Edgartown Lighthouse, Edgartown Harbor and Chappaquiddick Island, the Harbor View Hotel is flanked by historic homes from 19th Century whaling captains. With stately elm trees lining the streets, you can walk from the Harbor View to everything in Edgartown. They have been rated one of the “World’s Best Hotels” by Travel + Leisure and the “Best Overall Place to Stay” by Martha’s Vineyard Magazine.
Inns
Where you stay along the way.
Palmer House Inn
A charming bed and breakfast located in Falmouth, Massachusetts. Falmouth is a delightful New England village on Upper Cape Cod. Our romantic bed and breakfast is located in the Historic District, a quiet residential area of tree-lined streets, picket fences, colorful gardens, and elegant homes all decorated for the holidays. Beautiful beaches, quaint shops, ferry shuttles and excellent restaurants, are only a short stroll from our Cape Cod Bed and Breakfast.
Harbor View Hotel
Built in 1891, overlooking Martha’s Vineyard’s Edgartown Lighthouse, Edgartown Harbor and Chappaquiddick Island, the Harbor View Hotel is flanked by historic homes from 19th Century whaling captains. With stately elm trees lining the streets, you can walk from the Harbor View to everything in Edgartown. They have been rated one of the “World’s Best Hotels” by Travel + Leisure and the “Best Overall Place to Stay” by Martha’s Vineyard Magazine.
Inns
Where you stay along the way.
Palmer House Inn
A charming bed and breakfast located in Falmouth, Massachusetts. Falmouth is a delightful New England village on Upper Cape Cod. Our romantic bed and breakfast is located in the Historic District, a quiet residential area of tree-lined streets, picket fences, colorful gardens, and elegant homes all decorated for the holidays. Beautiful beaches, quaint shops, ferry shuttles and excellent restaurants, are only a short stroll from our Cape Cod Bed and Breakfast.
Harbor View Hotel
Built in 1891, overlooking Martha’s Vineyard’s Edgartown Lighthouse, Edgartown Harbor and Chappaquiddick Island, the Harbor View Hotel is flanked by historic homes from 19th Century whaling captains. With stately elm trees lining the streets, you can walk from the Harbor View to everything in Edgartown. They have been rated one of the “World’s Best Hotels” by Travel + Leisure and the “Best Overall Place to Stay” by Martha’s Vineyard Magazine.
Inns
Where you stay along the way.
Palmer House Inn
A charming bed and breakfast located in Falmouth, Massachusetts. Falmouth is a delightful New England village on Upper Cape Cod. Our romantic bed and breakfast is located in the Historic District, a quiet residential area of tree-lined streets, picket fences, colorful gardens, and elegant homes all decorated for the holidays. Beautiful beaches, quaint shops, ferry shuttles and excellent restaurants, are only a short stroll from our Cape Cod Bed and Breakfast.
Harbor View Hotel
Built in 1891, overlooking Martha’s Vineyard’s Edgartown Lighthouse, Edgartown Harbor and Chappaquiddick Island, the Harbor View Hotel is flanked by historic homes from 19th Century whaling captains. With stately elm trees lining the streets, you can walk from the Harbor View to everything in Edgartown. They have been rated one of the “World’s Best Hotels” by Travel + Leisure and the “Best Overall Place to Stay” by Martha’s Vineyard Magazine.
Guests say …
Quotes from guests about this tour:
"we just loved the ocean side rides."
Wendy G.
"Great location, beautiful views."
Jean
"Nice bike routes. Beautiful scenery. Frank was great! Very knowledgeable and interesting to talk to."
Allison L.
Gallery
Images from this tour. Click each to see it larger.
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