
Maryland: Eastern Shore & Chesapeake Bay
Guided Biking
- Daily Mileage: 6 - 33 miles|
- Biking: 1 - 4 hours|
Starting From
6-day Bike Tour Only
$2,545
Per person, double occupancy
Maryland: Eastern Shore & Chesapeake Bay
You won’t find another cycling tour like this splendid spin along Maryland’s Chesapeake Bay! With our deep local connections, VBT brings you a unique adventure featuring Southern warmth and hospitality. In the quaint coastal village of Rock Hall, you’ll be treated like family by your charismatic local innkeepers. Here, you might choose to relax—sipping cocktails by the water, taking a dip in the saltwater pool, or listening to the piano in your inn’s charming parlor. Pedaling the cheerful inlets of Chesapeake Bay, you’ll pass stately bayside homes, spin through the Blackwater National Wildlife Refuge, and visit the Harriet Tubman Underground Railroad State Park. For the quintessential Maryland experience, you’ll meet a local fisherman and cruise on his traditional skipjack while listening to spirited tales of life on the water.
Tour Highlights
- Sail the eastern shores with Captain Ed aboard the skipjack HM Krentz
- Feast on the region’s famous seafood
- Ride through the Blackwater National Wildlife Refuge, a haven for more than 250 bird species, and learn about Harriet Tubman at the newly opened Underground Railroad State Park and Visitor Center
- Travel on the country’s oldest privately owned ferry (since 1760), across the Tred-Avon River between Oxford and Bellevue
- Cycle the quiet country roads leading to the charming small towns of Oxford, St. Michaels, Rock Hall, and Easton
What to Expect
This tour offers easy ride options with only a few gradual hills. It is possible to ride the entire week without the need for assistance, but our VBT support vehicle is always available in cases of inclement weather or for those who wish to shorten their rides.
- Daily Mileage: 6 - 33 miles|
- Biking: 1 - 4 hours|
- Group Size: 20
Cycling
Cyclists
Support
Average High /
Low Temperature (°F):
Apr67º/48º
May75º/57º
Jun83º/65º
Sep80º/65º
Oct71º/53º
Average
Precipitation:
Apr2.9 in
May3.5 in
Jun4.4 in
Sep4.0 in
Oct3.4 in
Tour Only |
|
---|---|
5 nights in charming country inns | |
11 meals: 5 breakfasts, 3 lunches, 3 dinners | |
Transportation from Baltimore/Washington International Airport to Easton | |
Transportation from Rock Hall to Baltimore/Washington International Airport |

Road Bicycle (Carbon frame)
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Step-Through Electric-Assisted Bicycle (E-bike)
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Step-Through (Mixte Hybrid) Comfort Bicycle
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Step-Over (Diamond) Comfort Bicycle
See More >Biking Packages Include:
Custom VBT Bike and Helmet
Two Local, Bilingual Trip Leaders
Support Vehicle
Luggage Transportation
Ride with GPS and Daily Route Notes
Welcome Reception
Facilitated Cultural Experiences
Your Choice of VBT Branded Gear for Your Adventure
Accommodations (May vary depending on departure date. )

What a fantastic trip! Our tour leaders Mark and Barney took excellent care of us. They really worked with us to make sure we had a good comfortable riding experience. The rides, the food, the additional tours, and the hotels were all excellent and very enjoyable. It was wonderful to meet so many new friends from all over.
Maryland: Cycling the Chesapeake Bay
Beautiful area of our country to bike . The route was mostly flat and very scenic. Great tours of Chesapeake area. Sailing adventure of the Bay was delightful. Our guides were very informed about the area . They went out of their way to make us all comfortable.
Maryland: Cycling the Chesapeake Bay
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