Maryland: Cycling the Chesapeake Bay
The eastern shore of the Chesapeake Bay is loaded with tranquil, sublime bike routes along rural farm roads and quiet river pathways. As we pedal our way from Rock hall to Oxford, we’ll be surrounded by maritime traditions, Colonial history and plenty mouth-watering local seafood. We’ll explore artisans’ crafts stores while window shopping in downtown Easton and St. Michaels. And we’ll soak up some history both aboard a working skipjack and during a tour of the Chestertown, a former Royal British port. Embrace the serene natural setting of Eastern Neck Wildlife Refuge, home to more than 240 bird species, as well as a private 70-acre refuge that surrounds our country inn.
- Sail through the Kent Narrows aboard a skipjack and learn about local maritime tradition and oyster dredging from our skipper
- Picnic on the grounds of a family-run winery and enjoy a tasting offered by our hosts
- Enjoy a delicious lunch of Maryland’s famed Chesapeake blue crab
- Cycle the rural roads of Talbot County by green pastures, farms and the Choptank River, where bald eagles are often spotted
- Take a self-guided tour of the Chesapeake Bay Maritime Museum which includes a 19-th century lighthouse, a working boatyard, and the world's largest collection of Bay boats.
- Ride through historic Chestertown, one of Maryland's six Royal Ports of Entry in the 18-th century.
What to Expect
This tour offers options for easy rides throughout the trip. The terrain includes very few gradual hills. It’s possible to ride this entire week without the need for van shuttles. However, our VBT van support shuttle is always available in cases of inclement weather or for those who wish to shorten their rides.
Average Daily Mileage: 13 – 32 miles
Average Cycling Time: 2 – 4 1/2 hours
Average Daily Temperature (°F) – Easton
Apr 64° May 75° Aug 84° Sep 79° Oct 68°
Average Rainfall (in.) – Easton
Apr 3.4 May 3.5 Aug 4.6 Sep 3.5 Oct 3.2
- 5 nights in historic inns
- 11 meals – 5 breakfasts, 3 lunches, 3 dinners
- FREE use of our custom VBT bicycle and helmet
- Service of two VBT Trip Leaders
- FULL VAN SUPPORT
- Daily route directions and maps
- Welcome reception
- Sightseeing and cultural activities
- 5% Frequent Traveler Credit to use on your next VBT vacation
- Special Good Buy Discount