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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.

Itinerary

From start to finish, check out the route.

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.

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
Oct 10, 2021 Oct 15, 2021 $2695.00 1 to 4 spaces left! Reserve Reserve
May 01, 2022 May 06, 2022 $2695.00 Available! Reserve Reserve
May 08, 2022 May 13, 2022 $2695.00 Available! Reserve Reserve
Oct 02, 2022 Oct 07, 2022 $2695.00 Available! Reserve Reserve
Oct 09, 2022 Oct 14, 2022 $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: Oct 10, 2021
End: Oct 15, 2021
Cost: $2695.00
Availability: 1 to 4 spaces left!
Reserve
Start: May 01, 2022
End: May 06, 2022
Cost: $2695.00
Availability: Available!
Reserve
Start: May 08, 2022
End: May 13, 2022
Cost: $2695.00
Availability: Available!
Reserve
Start: Oct 02, 2022
End: Oct 07, 2022
Cost: $2695.00
Availability: Available!
Reserve
Start: Oct 09, 2022
End: Oct 14, 2022
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.

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