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Maryland Bay to Beach Bike Tour

  • Harbor sunset
  • Wetland biking
  • Red-winged blackbird
  • Steamed crab
  • Harriet Tubman Museum
  • Assateague Island pony
  • Beach at Assateague Island National Seashore
  • Assateague ponies by marsh
  • Mallard duck snuggled in pansies
DURATION
6 Day(s)
DAILY BIKING
9 to 50 miles
TRIP DIFFICULTY
1-Easier
REVIEWS
STARTING FROM
$2695
SINGLES ADD FROM
$600

Trip Overview

Celebrate spring or fall on the Tidewater Peninsula in Maryland! Gorgeous, easy cycling awaits you as you explore the coves and inlets of the Chesapeake Bay and stay at three exceptional inns. "Adventure Cyclist" magazine calls this “one of the 10 best places to tour in North America.” The roads are gently rolling as you wind your way through the Chesapeake estuary and its scenic shores. There’s the option for additional riding for the energetic, so this is a perfect tour to tune up your skills.

Known as Maryland’s Eastern Shore, this area offers you one of the country’s premier biking routes — taking quiet roads to beautiful Oxford and then crossing the Tred Avon River via the small Oxford-Bellevue Ferry. You stay at the edge of the bay on Tilghman Island and then on a tidal river next to the longest-running ferry in the country. Explore historic St. Michaels … enjoy wandering the streets lined with Colonial-era homes and elegant shops, strolling past the boat-lined marinas, and taking the included tour of the excellent Chesapeake Bay Maritime Museum. Spend a stunning day cycling through Blackwater National Wildlife Refuge — a haven for bald eagles, osprey and thousands of ducks and geese. The next day starts with a small ferry boat ride, then spin down quiet roads along the coast to another fishing village. Finally, spend two days exploring the ocean side of the peninsula … including visiting the famous wild ponies at Assateague Island National Seashore.

DAY 1 - Arrival Day
Distance 10 or 22 miles | Terrain: Easier | The Wylder Hotel, Tilghman Island
Begin your tour on Tilghman Island at the Wylder Inn. After a bike fitting, you have a shakeout ride at 3 p.m. Explore the Tilghman Island area and bike up to another local fishing village. Dinner is at the Wylder Inn, leaving plenty of time to explore the shore of the Chesapeake and the small village on Tilghman Island.
DAY 2 - Easton and the Oxford-Bellevue Ferry
Distance: 25, 35 or 38 miles | Terrain: Easier | The Wylder Hotel
On this tour you enjoy what is considered one of the premier coastal biking routes in the eastern U.S. Ride a mix of shoulders and quiet roads to St. Michaels and then make a short crossing of the Tred Avon River on the Oxford-Bellevue Ferry. Founded in 1683, this privately owned ferry is believed to be the oldest in the country. Spin through the tree-lined village of Oxford well-known for boat building and maritime activities since the early settlers arrived here. Once in Oxford village, there’s a great place for a bayside lunch … and perhaps a visit to the Scottish Highland Creamery for a scoop of Victor Barlow’s homemade ice cream. After lunch, cross the Tred Avon on the ferry again and cycle back into St. Michaels. Guests can change there and stay for the afternoon to explore the village or bike or shuttle back to the Wylder Inn … and return to St. Michaels in the late afternoon. Dinner is in St. Michaels.
DAY 3 - Wildlife Refuge & Harriet Tubman History
Distance: 38 or 48 miles | Terrain: Easier | Whitehaven Hotel
Today’s spectacular ride takes you through the Blackwater National Wildlife Refuge with an included picnic lunch. This 25,000-acre preserve was originally established in 1933 as a haven for ducks and geese migrating along the Atlantic Flyway (upwards of 35,000 geese and 15,000 ducks visit each year) and is host to one of the largest breeding populations of bald eagles on the East Coast. It is also a haven for several troubled species including the endangered Delmarva fox squirrel and the migrant peregrine falcon. "Time Magazine" once called this refuge “nature on the throne of her glory,” and you will quickly understand why. You also stop in the recently established Harriett Tubman Underground Railroad National Historical Park, with an option to tour the well-designed visitor center and see several historic sites. After your ride, there’s a short shuttle to the Whitehaven Hotel — located at the ferry crossing on the tidal Wicomico River.
DAY 4 - Deal Island & Chesapeake Lowlands
Distance: 38 or 48 miles | Terrain: Easier | The Atlantic Hotel
Start the day with a ride across a small rope-drawn ferry that is considered the oldest ferry in the U.S. Continue along quiet roads and past wetlands to Deal Island, another small fishing village overlooking the Chesapeake. Nearby is Smith Island in the Chesapeake, so be sure to try a delicious slice of the famous many-layered Smith Island cake with your lunch! End the day with a transfer to Berlin, Maryland, and the Atlantic Hotel. Scenic Berlin has 47 structures on the National Register of Historic Places (including our hotel) and has served as the backdrop for movies such as “Runaway Bride” and “Tuck Everlasting.” You also have a chance to stop at a couple of the top craft breweries on Maryland’s Eastern Shore this day: Evolution Brewery in Salisbury and Burley Oak Brewing in Berlin. Dinner is on your own in Berlin.
DAY 5 - Snow Hill & Assateague Island
Distance: 31 or 50 miles | Terrain: Easier | The Atlantic Hotel
Ride a loop to Snow Hill, Maryland, where you enjoy lunch in another historic riverside town. After lunch, head back toward Berlin and out to Assateague Island for an afternoon walk along the beach and visits with the famous Assateague ponies. You can bike or van back after lunch, and the evening ends with a celebration dinner in Berlin at the Atlantic Hotel. There’s also time to visit one of Maryland’s best craft breweries, Burley Oak.
DAY 6 - Departure Day
Distance: 24 or 29 miles | Terrain: Easier
On your final day, take a lovely early morning bike ride or van trip back out to Assateague Island for the sunrise over the Atlantic, if you are an early riser. Riders can enjoy a final morning of relaxed distances or a longer ride along the coastal area before your shuttle back to your car at Tilghman Island or to Easton Airport for transport options to BWI airport.
DAY 1 - Arrival Day
St. Michaels Harbour Inn
We begin our tour in Saint Michaels, a quaint waterfront village situated on a picturesque peninsula between Tilghman Island and Easton. It’s well known for its interesting mix of history, shops, and small town charm. The town’s historic streets are lined with Colonial-era houses and shops, evidence that Saint Michaels has been a shipping and trading center since the 1630s. While in Saint Michaels, we are guests at the beautiful Harbour Inn, where each of our elegant rooms enjoys a beautiful view of the harbor and the Miles River, and where you can opt for a relaxing spa treatment or massage to unwind after your day of cycling and sightseeing.
DAY 2 - Easton and the Oxford-Bellevue Ferry
Distance: 26 or 38 miles | Terrain: Easier | Harbour Inn
On this tour we treat you to what is considered one of the premier coastal biking routes on the East Coast. We ride the bike path through Easton and then wend our way along back roads to Oxford, a charming, tree-lined village on the banks of the Tred Avon River that has been well known for its boat building and maritime activities since the early settlers first arrived here. We recommend a great place for a bayside lunch and our exploration of Oxford often ends with a visit to the Scottish Highland Creamery for a scoop of Victor Barlow’s homemade ice cream. After lunch Captain Tom Bixler welcomes us aboard the small Oxford-Bellevue Ferry. Founded in 1683, this privately owned ferry is believed to be the oldest in the country. After crossing we ride pretty back roads through Royal Oak and Bellevue back to Saint Michaels.
DAY 3 - Tilghman's Island & Maritime History
Distance: 18 miles | Terrain: Easier | Harbour Inn
This day is highlighted by a trip to the end of Tilghman’s Island through estuaries, farm fields and the view across the Chesapeake Bay. Crossing the drawbridge on Tilghman’s Island, you arrive on one of the Chesapeake’s iconic locations, where fishing and crabbing are still a way of life. Have lunch at Two If By Sea, and take time to explore the history- and Bay-themed bookstore next door. Return to Saint Michaels by van to enjoy more corners of the peninsula. And visit the fascinating Chesapeake Bay Maritime Museum, where we can learn about the history of the Bay, and its traditions in boat building, commercial fishing, yachting and navigation. There are 23 buildings here on 18 acres with interactive exhibits, the popular Hooper Straight Lighthouse, and several historic vessels docked at the waterfront boat yard.
DAY 4 - Wildlife Refuge & Harriet Tubman History
Distance: 38 or 48 miles | Terrain: Easier | The Atlantic Hotel
On Wednesday, we have a spectacular ride that takes us through the Blackwater National Wildlife Refuge. This 25,000 acre preserve was originally established in 1933 as a haven for ducks and geese migrating along the Atlantic Flyway (upwards of 35,000 geese and 15,000 ducks visit each year) and is host to one of the largest breeding populations of bald eagles on the East Coast. It is also a haven for several troubled species including the endangered Delmarva fox squirrel and the migrant peregrine falcon. Time magazine once called this refuge “nature on the throne of her glory,” and you will quickly understand why. We also stop in the recently established Harriett Tubman Underground Railroad National Historical Park, touring the well-designed visitor center and seeing several historic sites. We end the day with a transfer to Berlin, Maryland, and the Atlantic Hotel. Scenic Berlin has 47 structures on the National Register of Historic Places (including our hotel) and has served as the backdrop for movies such as Runaway Bride and Tuck Everlasting.
DAY 5 - Snow Hill & Assateague Island
Distance: 31 or 50 miles | Terrain: Easier | The Atlantic Hotel
On Thursday, we ride a loop to Snow Hill, Maryland, where we enjoy lunch at another historic riverside town. After lunch, we’ll head back toward Berlin and out to Assateague Island for an afternoon walk along the beach and visits with the famous Assateague ponies. You can bike or van after lunch, and the evening will end with a celebration dinner in Berlin at the Atlantic Hotel. There will also be time to visit one of Maryland’s best craft breweries, Burley Oak.
DAY 6 - Departure Day
Distance: 24 or 29 miles | Terrain: Easier
On our final day, we take a lovely early morning ride or van trip back out to Assateague for the sunrise over the Atlantic, if you are an early riser. Riders can enjoy a final morning of relaxed distances or a longer ride along the coastal area before our shuttle back to Saint Michaels.
DAY 1 - Arrival Day
St. Michaels Harbour Inn
We begin our tour in Saint Michaels, a quaint waterfront village situated on a picturesque peninsula between Tilghman Island and Easton. It’s well known for its interesting mix of history, shops, and small town charm. The town’s historic streets are lined with Colonial-era houses and shops, evidence that Saint Michaels has been a shipping and trading center since the 1630s. While in Saint Michaels, we are guests at the beautiful Harbour Inn, where each of our elegant rooms enjoys a beautiful view of the harbor and the Miles River, and where you can opt for a relaxing spa treatment or massage to unwind after your day of cycling and sightseeing.
DAY 2 - Easton and the Oxford-Bellevue Ferry
Distance: 26 or 38 miles | Terrain: Easier | Harbour Inn
On this tour we treat you to what is considered one of the premier coastal biking routes on the East Coast. We ride the bike path through Easton and then wend our way along back roads to Oxford, a charming, tree-lined village on the banks of the Tred Avon River that has been well known for its boat building and maritime activities since the early settlers first arrived here. We recommend a great place for a bayside lunch and our exploration of Oxford often ends with a visit to the Scottish Highland Creamery for a scoop of Victor Barlow’s homemade ice cream. After lunch Captain Tom Bixler welcomes us aboard the small Oxford-Bellevue Ferry. Founded in 1683, this privately owned ferry is believed to be the oldest in the country. After crossing we ride pretty back roads through Royal Oak and Bellevue back to Saint Michaels.
DAY 3 - Tilghman's Island & Maritime History
Distance: 18 miles | Terrain: Easier | Harbour Inn
This day is highlighted by a trip to the end of Tilghman’s Island through estuaries, farm fields and the view across the Chesapeake Bay. Crossing the drawbridge on Tilghman’s Island, you arrive on one of the Chesapeake’s iconic locations, where fishing and crabbing are still a way of life. Have lunch at Two If By Sea, and take time to explore the history- and Bay-themed bookstore next door. Return to Saint Michaels by van to enjoy more corners of the peninsula. And visit the fascinating Chesapeake Bay Maritime Museum, where we can learn about the history of the Bay, and its traditions in boat building, commercial fishing, yachting and navigation. There are 23 buildings here on 18 acres with interactive exhibits, the popular Hooper Straight Lighthouse, and several historic vessels docked at the waterfront boat yard.
DAY 4 - Wildlife Refuge & Harriet Tubman History
Distance: 38 or 48 miles | Terrain: Easier | The Atlantic Hotel
On Wednesday, we have a spectacular ride that takes us through the Blackwater National Wildlife Refuge. This 25,000 acre preserve was originally established in 1933 as a haven for ducks and geese migrating along the Atlantic Flyway (upwards of 35,000 geese and 15,000 ducks visit each year) and is host to one of the largest breeding populations of bald eagles on the East Coast. It is also a haven for several troubled species including the endangered Delmarva fox squirrel and the migrant peregrine falcon. Time magazine once called this refuge “nature on the throne of her glory,” and you will quickly understand why. We also stop in the recently established Harriett Tubman Underground Railroad National Historical Park, touring the well-designed visitor center and seeing several historic sites. We end the day with a transfer to Berlin, Maryland, and the Atlantic Hotel. Scenic Berlin has 47 structures on the National Register of Historic Places (including our hotel) and has served as the backdrop for movies such as Runaway Bride and Tuck Everlasting.
DAY 5 - Snow Hill & Assateague Island
Distance: 31 or 50 miles | Terrain: Easier | The Atlantic Hotel
On Thursday, we ride a loop to Snow Hill, Maryland, where we enjoy lunch at another historic riverside town. After lunch, we’ll head back toward Berlin and out to Assateague Island for an afternoon walk along the beach and visits with the famous Assateague ponies. You can bike or van after lunch, and the evening will end with a celebration dinner in Berlin at the Atlantic Hotel. There will also be time to visit one of Maryland’s best craft breweries, Burley Oak.
DAY 6 - Departure Day
Distance: 24 or 29 miles | Terrain: Easier
On our final day, we take a lovely early morning ride or van trip back out to Assateague for the sunrise over the Atlantic, if you are an early riser. Riders can enjoy a final morning of relaxed distances or a longer ride along the coastal area before our shuttle back to Saint Michaels.
DAY 1 - Arrival Day
St. Michaels Harbour Inn
We begin our tour in Saint Michaels, a quaint waterfront village situated on a picturesque peninsula between Tilghman Island and Easton. It’s well known for its interesting mix of history, shops, and small town charm. The town’s historic streets are lined with Colonial-era houses and shops, evidence that Saint Michaels has been a shipping and trading center since the 1630s. While in Saint Michaels, we are guests at the beautiful Harbour Inn, where each of our elegant rooms enjoys a beautiful view of the harbor and the Miles River, and where you can opt for a relaxing spa treatment or massage to unwind after your day of cycling and sightseeing.
DAY 2 - Easton and the Oxford-Bellevue Ferry
Distance: 26 or 38 miles | Terrain: Easier | Harbour Inn
On this tour we treat you to what is considered one of the premier coastal biking routes on the East Coast. We ride the bike path through Easton and then wend our way along back roads to Oxford, a charming, tree-lined village on the banks of the Tred Avon River that has been well known for its boat building and maritime activities since the early settlers first arrived here. We recommend a great place for a bayside lunch and our exploration of Oxford often ends with a visit to the Scottish Highland Creamery for a scoop of Victor Barlow’s homemade ice cream. After lunch Captain Tom Bixler welcomes us aboard the small Oxford-Bellevue Ferry. Founded in 1683, this privately owned ferry is believed to be the oldest in the country. After crossing we ride pretty back roads through Royal Oak and Bellevue back to Saint Michaels.
DAY 3 - Tilghman's Island & Maritime History
Distance: 18 miles | Terrain: Easier | Harbour Inn
This day is highlighted by a trip to the end of Tilghman’s Island through estuaries, farm fields and the view across the Chesapeake Bay. Crossing the drawbridge on Tilghman’s Island, you arrive on one of the Chesapeake’s iconic locations, where fishing and crabbing are still a way of life. Have lunch at Two If By Sea, and take time to explore the history- and Bay-themed bookstore next door. Return to Saint Michaels by van to enjoy more corners of the peninsula. And visit the fascinating Chesapeake Bay Maritime Museum, where we can learn about the history of the Bay, and its traditions in boat building, commercial fishing, yachting and navigation. There are 23 buildings here on 18 acres with interactive exhibits, the popular Hooper Straight Lighthouse, and several historic vessels docked at the waterfront boat yard.
DAY 4 - Wildlife Refuge & Harriet Tubman History
Distance: 38 or 48 miles | Terrain: Easier | The Atlantic Hotel
On Wednesday, we have a spectacular ride that takes us through the Blackwater National Wildlife Refuge. This 25,000 acre preserve was originally established in 1933 as a haven for ducks and geese migrating along the Atlantic Flyway (upwards of 35,000 geese and 15,000 ducks visit each year) and is host to one of the largest breeding populations of bald eagles on the East Coast. It is also a haven for several troubled species including the endangered Delmarva fox squirrel and the migrant peregrine falcon. Time magazine once called this refuge “nature on the throne of her glory,” and you will quickly understand why. We also stop in the recently established Harriett Tubman Underground Railroad National Historical Park, touring the well-designed visitor center and seeing several historic sites. We end the day with a transfer to Berlin, Maryland, and the Atlantic Hotel. Scenic Berlin has 47 structures on the National Register of Historic Places (including our hotel) and has served as the backdrop for movies such as Runaway Bride and Tuck Everlasting.
DAY 5 - Snow Hill & Assateague Island
Distance: 31 or 50 miles | Terrain: Easier | The Atlantic Hotel
On Thursday, we ride a loop to Snow Hill, Maryland, where we enjoy lunch at another historic riverside town. After lunch, we’ll head back toward Berlin and out to Assateague Island for an afternoon walk along the beach and visits with the famous Assateague ponies. You can bike or van after lunch, and the evening will end with a celebration dinner in Berlin at the Atlantic Hotel. There will also be time to visit one of Maryland’s best craft breweries, Burley Oak.
DAY 6 - Departure Day
Distance: 24 or 29 miles | Terrain: Easier
On our final day, we take a lovely early morning ride or van trip back out to Assateague for the sunrise over the Atlantic, if you are an early riser. Riders can enjoy a final morning of relaxed distances or a longer ride along the coastal area before our shuttle back to Saint Michaels.
DAY 1 - Arrival Day
St. Michaels Harbour Inn
We begin our tour in Saint Michaels, a quaint waterfront village situated on a picturesque peninsula between Tilghman Island and Easton. It’s well known for its interesting mix of history, shops, and small town charm. The town’s historic streets are lined with Colonial-era houses and shops, evidence that Saint Michaels has been a shipping and trading center since the 1630s. While in Saint Michaels, we are guests at the beautiful Harbour Inn, where each of our elegant rooms enjoys a beautiful view of the harbor and the Miles River, and where you can opt for a relaxing spa treatment or massage to unwind after your day of cycling and sightseeing.
DAY 2 - Easton and the Oxford-Bellevue Ferry
Distance: 26 or 38 miles | Terrain: Easier | Harbour Inn
On this tour we treat you to what is considered one of the premier coastal biking routes on the East Coast. We ride the bike path through Easton and then wend our way along back roads to Oxford, a charming, tree-lined village on the banks of the Tred Avon River that has been well known for its boat building and maritime activities since the early settlers first arrived here. We recommend a great place for a bayside lunch and our exploration of Oxford often ends with a visit to the Scottish Highland Creamery for a scoop of Victor Barlow’s homemade ice cream. After lunch Captain Tom Bixler welcomes us aboard the small Oxford-Bellevue Ferry. Founded in 1683, this privately owned ferry is believed to be the oldest in the country. After crossing we ride pretty back roads through Royal Oak and Bellevue back to Saint Michaels.
DAY 3 - Tilghman's Island & Maritime History
Distance: 18 miles | Terrain: Easier | Harbour Inn
This day is highlighted by a trip to the end of Tilghman’s Island through estuaries, farm fields and the view across the Chesapeake Bay. Crossing the drawbridge on Tilghman’s Island, you arrive on one of the Chesapeake’s iconic locations, where fishing and crabbing are still a way of life. Have lunch at Two If By Sea, and take time to explore the history- and Bay-themed bookstore next door. Return to Saint Michaels by van to enjoy more corners of the peninsula. And visit the fascinating Chesapeake Bay Maritime Museum, where we can learn about the history of the Bay, and its traditions in boat building, commercial fishing, yachting and navigation. There are 23 buildings here on 18 acres with interactive exhibits, the popular Hooper Straight Lighthouse, and several historic vessels docked at the waterfront boat yard.
DAY 4 - Wildlife Refuge & Harriet Tubman History
Distance: 38 or 48 miles | Terrain: Easier | The Atlantic Hotel
On Wednesday, we have a spectacular ride that takes us through the Blackwater National Wildlife Refuge. This 25,000 acre preserve was originally established in 1933 as a haven for ducks and geese migrating along the Atlantic Flyway (upwards of 35,000 geese and 15,000 ducks visit each year) and is host to one of the largest breeding populations of bald eagles on the East Coast. It is also a haven for several troubled species including the endangered Delmarva fox squirrel and the migrant peregrine falcon. Time magazine once called this refuge “nature on the throne of her glory,” and you will quickly understand why. We also stop in the recently established Harriett Tubman Underground Railroad National Historical Park, touring the well-designed visitor center and seeing several historic sites. We end the day with a transfer to Berlin, Maryland, and the Atlantic Hotel. Scenic Berlin has 47 structures on the National Register of Historic Places (including our hotel) and has served as the backdrop for movies such as Runaway Bride and Tuck Everlasting.
DAY 5 - Snow Hill & Assateague Island
Distance: 31 or 50 miles | Terrain: Easier | The Atlantic Hotel
On Thursday, we ride a loop to Snow Hill, Maryland, where we enjoy lunch at another historic riverside town. After lunch, we’ll head back toward Berlin and out to Assateague Island for an afternoon walk along the beach and visits with the famous Assateague ponies. You can bike or van after lunch, and the evening will end with a celebration dinner in Berlin at the Atlantic Hotel. There will also be time to visit one of Maryland’s best craft breweries, Burley Oak.
DAY 6 - Departure Day
Distance: 24 or 29 miles | Terrain: Easier
On our final day, we take a lovely early morning ride or van trip back out to Assateague for the sunrise over the Atlantic, if you are an early riser. Riders can enjoy a final morning of relaxed distances or a longer ride along the coastal area before our shuttle back to Saint Michaels.
DAY 1 - Arrival Day
St. Michaels Harbour Inn
We begin our tour in Saint Michaels, a quaint waterfront village situated on a picturesque peninsula between Tilghman Island and Easton. It’s well known for its interesting mix of history, shops, and small town charm. The town’s historic streets are lined with Colonial-era houses and shops, evidence that Saint Michaels has been a shipping and trading center since the 1630s. While in Saint Michaels, we are guests at the beautiful Harbour Inn, where each of our elegant rooms enjoys a beautiful view of the harbor and the Miles River, and where you can opt for a relaxing spa treatment or massage to unwind after your day of cycling and sightseeing.
DAY 2 - Easton and the Oxford-Bellevue Ferry
Distance: 26 or 38 miles | Terrain: Easier | Harbour Inn
On this tour we treat you to what is considered one of the premier coastal biking routes on the East Coast. We ride the bike path through Easton and then wend our way along back roads to Oxford, a charming, tree-lined village on the banks of the Tred Avon River that has been well known for its boat building and maritime activities since the early settlers first arrived here. We recommend a great place for a bayside lunch and our exploration of Oxford often ends with a visit to the Scottish Highland Creamery for a scoop of Victor Barlow’s homemade ice cream. After lunch Captain Tom Bixler welcomes us aboard the small Oxford-Bellevue Ferry. Founded in 1683, this privately owned ferry is believed to be the oldest in the country. After crossing we ride pretty back roads through Royal Oak and Bellevue back to Saint Michaels.
DAY 3 - Tilghman's Island & Maritime History
Distance: 18 miles | Terrain: Easier | Harbour Inn
This day is highlighted by a trip to the end of Tilghman’s Island through estuaries, farm fields and the view across the Chesapeake Bay. Crossing the drawbridge on Tilghman’s Island, you arrive on one of the Chesapeake’s iconic locations, where fishing and crabbing are still a way of life. Have lunch at Two If By Sea, and take time to explore the history- and Bay-themed bookstore next door. Return to Saint Michaels by van to enjoy more corners of the peninsula. And visit the fascinating Chesapeake Bay Maritime Museum, where we can learn about the history of the Bay, and its traditions in boat building, commercial fishing, yachting and navigation. There are 23 buildings here on 18 acres with interactive exhibits, the popular Hooper Straight Lighthouse, and several historic vessels docked at the waterfront boat yard.
DAY 4 - Wildlife Refuge & Harriet Tubman History
Distance: 38 or 48 miles | Terrain: Easier | The Atlantic Hotel
On Wednesday, we have a spectacular ride that takes us through the Blackwater National Wildlife Refuge. This 25,000 acre preserve was originally established in 1933 as a haven for ducks and geese migrating along the Atlantic Flyway (upwards of 35,000 geese and 15,000 ducks visit each year) and is host to one of the largest breeding populations of bald eagles on the East Coast. It is also a haven for several troubled species including the endangered Delmarva fox squirrel and the migrant peregrine falcon. Time magazine once called this refuge “nature on the throne of her glory,” and you will quickly understand why. We also stop in the recently established Harriett Tubman Underground Railroad National Historical Park, touring the well-designed visitor center and seeing several historic sites. We end the day with a transfer to Berlin, Maryland, and the Atlantic Hotel. Scenic Berlin has 47 structures on the National Register of Historic Places (including our hotel) and has served as the backdrop for movies such as Runaway Bride and Tuck Everlasting.
DAY 5 - Snow Hill & Assateague Island
Distance: 31 or 50 miles | Terrain: Easier | The Atlantic Hotel
On Thursday, we ride a loop to Snow Hill, Maryland, where we enjoy lunch at another historic riverside town. After lunch, we’ll head back toward Berlin and out to Assateague Island for an afternoon walk along the beach and visits with the famous Assateague ponies. You can bike or van after lunch, and the evening will end with a celebration dinner in Berlin at the Atlantic Hotel. There will also be time to visit one of Maryland’s best craft breweries, Burley Oak.
DAY 6 - Departure Day
Distance: 24 or 29 miles | Terrain: Easier
On our final day, we take a lovely early morning ride or van trip back out to Assateague for the sunrise over the Atlantic, if you are an early riser. Riders can enjoy a final morning of relaxed distances or a longer ride along the coastal area before our shuttle back to Saint Michaels.

Map

Dates & Pricing

Prices are based on double occupancy. 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.

Start End Cost Availability
May 02, 2021 May 07, 2021 $2695.00 1 to 4 spaces left! Reserve Reserve
Oct 03, 2021 Oct 08, 2021 $2695.00 Available! Reserve Reserve
Oct 10, 2021 Oct 15, 2021 $2695.00 Available! Reserve Reserve

What’s Included

Two leaders, Oxford ferry, Whitehaven ferry, entry to Blackwater Preserve, entry to Chesapeake Bay Maritime Museum, 5 nights’ lodging, 5 breakfasts, 1 picnic lunch, 4 dinners (you are on your own for 1 dinner in Berlin), bicycle and helmet. Free transfer provided from/to Easton, Maryland bus station/airport. Airfare not included.

Dates & Pricing

Prices are based on double occupancy. 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.

Start: May 02, 2021
End: May 07, 2021
Cost: $2695.00
Availability: 1 to 4 spaces left!
Reserve
Start: Oct 03, 2021
End: Oct 08, 2021
Cost: $2695.00
Availability: Available!
Reserve
Start: Oct 10, 2021
End: Oct 15, 2021
Cost: $2695.00
Availability: Available!
Reserve

What’s Included

Two leaders, Oxford ferry, Whitehaven ferry, entry to Blackwater Preserve, entry to Chesapeake Bay Maritime Museum, 5 nights’ lodging, 5 breakfasts, 1 picnic lunch, 4 dinners (you are on your own for 1 dinner in Berlin), bicycle and helmet. Free transfer provided from/to Easton, Maryland bus station/airport. Airfare not included.

Inns

Where you stay along the way.

Wylder Hotel
The Wylder has been welcoming guests since 1898. It's a place where guests can reconnect with nature and one another. This bayside retreat is located on a small 3-mile island on the Chesapeake Bay. This small watermen’s town just may be the perfect retreat. The resort features 9.5 acres and only 50 hotel rooms primarily with outdoor access and no public elevators or open lobbies.
Whitehaven Hotel
In 1995, the 19th century Whitehaven Hotel was saved from deterioration and decline through the cooperative efforts of local residents, the Maryland Historic trust and by those captivated by its charming location in a riverfront Eastern Shore village at the Whitehaven ferry, minutes from the Chesapeake Bay. The Hotel, now one of the last of its kind, provided lodging for travelers crossing the Wicomico by horse to Quantico, Salisbury and Princess Anne and by steamship to ports as far as Baltimore.
The Atlantic Hotel
The historic Atlantic Hotel has served the town of Berlin for the past 120 years with outstanding cuisine, gracious service and upscale accommodations in Victorian-period style.

Inns

Where you stay along the way.

St. Michaels Harbour Inn
St. Michaels Harbour Inn, Marina & Spa is a year-round luxury resort, situated right off the Miles River, on the harbor in historic St. Michaels, on Maryland’s Eastern Shore.
The Atlantic Hotel
The historic Atlantic Hotel has served the town of Berlin for the past 120 years with outstanding cuisine, gracious service and upscale accommodations in Victorian-period style.

Inns

Where you stay along the way.

St. Michaels Harbour Inn
St. Michaels Harbour Inn, Marina & Spa is a year-round luxury resort, situated right off the Miles River, on the harbor in historic St. Michaels, on Maryland’s Eastern Shore.
The Atlantic Hotel
The historic Atlantic Hotel has served the town of Berlin for the past 120 years with outstanding cuisine, gracious service and upscale accommodations in Victorian-period style.

Inns

Where you stay along the way.

St. Michaels Harbour Inn
St. Michaels Harbour Inn, Marina & Spa is a year-round luxury resort, situated right off the Miles River, on the harbor in historic St. Michaels, on Maryland’s Eastern Shore.
The Atlantic Hotel
The historic Atlantic Hotel has served the town of Berlin for the past 120 years with outstanding cuisine, gracious service and upscale accommodations in Victorian-period style.

Inns

Where you stay along the way.

St. Michaels Harbour Inn
St. Michaels Harbour Inn, Marina & Spa is a year-round luxury resort, situated right off the Miles River, on the harbor in historic St. Michaels, on Maryland’s Eastern Shore.
The Atlantic Hotel
The historic Atlantic Hotel has served the town of Berlin for the past 120 years with outstanding cuisine, gracious service and upscale accommodations in Victorian-period style.

Inns

Where you stay along the way.

St. Michaels Harbour Inn
St. Michaels Harbour Inn, Marina & Spa is a year-round luxury resort, situated right off the Miles River, on the harbor in historic St. Michaels, on Maryland’s Eastern Shore.
The Atlantic Hotel
The historic Atlantic Hotel has served the town of Berlin for the past 120 years with outstanding cuisine, gracious service and upscale accommodations in Victorian-period style.

Guests say …

Quotes from guests about this tour:


"Guides were awesome, everything about the Blackwater and Berlin part of the trip, flexibility with distances."
Gloria A

"Discovery did their usually fabulous job of taking care of the details."
Sarah & Rich.

"Every day I had great moments.  It is a trip I will long remember fondly."
Dierdre C.

Gallery

Images from this tour. Click each to see it larger.

Harbor sunset Wetland biking Red-winged blackbird Steamed crab Harriet Tubman Museum Assateague Island pony Beach at Assateague Island National Seashore Assateague ponies by marsh Mallard duck snuggled in pansies