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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
$3495
SINGLES ADD FROM
$950

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. (Rooms with 2 beds are limited for this tour, but alternate lodging may be possible. Please contact our office for details.)

Surfaces for this tour: 99% Paved and 1% Gravel.

Itinerary

From start to finish, check out the route.

DAY 1 - Arrival Day
Distance 10 or 22 miles | Terrain: Easier | Knapp's Narrows Marina & Inn
Begin your tour on Tilghman Island at the Knapp's Narrows Marina & 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 together tonight, 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 |Knapp's Narrows Marina & Inn
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, which has been well-known for boat building and maritime activities since the early settlers arrived here. After exploring, cross the Tred Avon on the ferry again and cycle back into St. Michaels for lunch. Guests can change there and stay for the afternoon to explore the village or bike or shuttle back to the 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. Cycle on quiet roads to Sugar Water Manor for a special picnic lunch and visit to this lovely waterfront farm. Here there are rescued farm animals to visit … plus, kayaks and a pool for your use. Or do some added miles on your bike. 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." 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 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.

Start End Cost Availability
Oct 06, 2024 Oct 11, 2024 $3495.00 Available! Reserve Reserve

What’s Included

5 nights’ lodging in rooms with 1 bed, 4 breakfasts, 1 brunch, 2 picnic lunches, 4 dinners (you are on your own for 1 dinner in Berlin). Free transfer provided at one time from/to Easton, Maryland bus station/airport. Oxford ferry, Whitehaven ferry, entry to Blackwater National Wildlife Refuge, entry to Chesapeake Bay Maritime Museum. We also include detailed maps and itineraries, experienced guides, full van support — plus use of a bike and helmet. Airfare is 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.

Start: Oct 06, 2024
End: Oct 11, 2024
Cost: $3495.00
Availability: Available!
Reserve

What’s Included

5 nights’ lodging in rooms with 1 bed, 4 breakfasts, 1 brunch, 2 picnic lunches, 4 dinners (you are on your own for 1 dinner in Berlin). Free transfer provided at one time from/to Easton, Maryland bus station/airport. Oxford ferry, Whitehaven ferry, entry to Blackwater National Wildlife Refuge, entry to Chesapeake Bay Maritime Museum. We also include detailed maps and itineraries, experienced guides, full van support — plus use of a bike and helmet. Airfare is not included.

Inns

Where you stay along the way.

Knapp's Narrows Marina & Inn
Knapps Narrows Marina & Inn is located on Maryland’s Eastern Shore in Tilghman, adjacent to the Knapps Narrows Bridge. The property features a 20-room waterfront inn with sweeping views of the Chesapeake Bay. Each room has its own waterfront balcony or patio.
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 usual fabulous job of taking care of the details."
— Sarah.

"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