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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.

Positive Impact

VBT is proud to support Wine to Water with a donation on behalf of each guest on this tour. Wine to Water is an international organization providing access to clean drinking water and emergency supplies in water-challenged regions. We believe in giving back to the places that have enriched the lives of our guests. We’re committed to identifying and supporting sustainable initiatives in a variety of areas including education, world health, economic equality, safe drinking water, the environment, and the preservation of cultural traditions.

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
Activity Easy
Bar Graph Beginner - Experienced
Vehicle Support Vehicle

Average High /
Low Temperature (°F):







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

2025 2024

Step-Through Electric-Assisted Bicycle (E-bike)

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Road Bicycle (Carbon frame)

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Step-Through (Mixte Hybrid) Comfort Bicycle

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Step-Over (Diamond) Comfort Bicycle

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2025 2024

Step-Through Electric-Assisted Bicycle (E-bike)

See More >

Road Bicycle (Carbon frame)

See More >

Step-Through (Mixte Hybrid) Comfort Bicycle

See More >

Step-Over (Diamond) Comfort Bicycle

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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


Sun, Apr 27 to Fri, May 2, 2025

Show Itinerary:

VBT provides a shuttle from Baltimore-Washington International Airport (BWI) to the Tidewater Inn in Easton, departing at 1:00 p.m.

Travel to Easton and the Tidewater Inn where your group and trip leaders will meet at 3:00 p.m. for a safety and bike-fitting session, followed by a short warm-up ride. At 5:00 p.m., meet up with the group for an orientation and welcome reception before a 7:00 p.m. dinner at the inn.

Today's Ride Choices

Afternoon: Warm-up Easton — 6 miles

What to Expect:

Your warm-up ride gives you the opportunity to get acquainted with the bicycle that will be your stalwart companion for the week. Leave the Tidewater Inn and enjoy a ride on the quiet Easton Rails to Trails path.

Cumulative Distance Range: 6 miles

Included Meals: Dinner

Today you are in for a treat. The Oxford/St. Michaels Loop is considered one of the premiere biking routes on the East Coast. You will ride a clockwise route from your inn, through Oxford, a 17th-century town with a long tradition of boat building. Cutts and Case Boatyard has a number of classic wooden boats on display, two short blocks from our rest stop.

The modest Oxford-Bellevue ferry, the oldest privately owned ferry still in operation in America will carry you across the Tred Avon River. From Bellevue, you will ride through the small town of Royal Oak, stopping for an included lunch in St. Michaels, a small bayside town on a long, narrow neck of land.

Then board the HM Krentz and sail the Eastern Bay. Our skipper, Captain Ed, has spent more than 35 years dredging oysters and sailing skipjacks and his boat is a broad-beamed former working skipjack. Her stable decks are perfect for enjoying the bracing sea air. There is time to visit the impressive Chesapeake Bay Maritime Museum for a self-guided tour. The museum has over 10 exhibit buildings, the 1879 Hooper Strait Lighthouse, a working boatyard, and the world’s largest collection of Bay boats. St. Michaels also offers wonderful shopping, snacking, and plenty of people-watching opportunities.

Mileage hounds may increase your ride total by riding toward Tilghman Island from St. Michaels after lunch before backtracking to St. Michaels.

Easton has been featured on many “best small towns in America” lists. The village is small in scale but packed with great dining, antique shops, galleries, and stores. The Tidewater Inn has played a central role in the village since 1712. The hotel features great eating and drinking at Hunter’s Tavern.

This evening you will be on your own for dinner and additional exploring. Your VBT trip leaders will be happy to give you suggestions for great local restaurants.

Today's Ride Choices

Morning: Easton to St. Michael’s — 19 miles

Afternoon: St. Michael’s to Claiborne Landing to St. Michael’s — 10 miles

What to Expect:

The St. Michael’s Loop is recognized as one of the premier bike trails in the Mid-Atlantic region. The popular tourist destination of St. Michaels has many shops. Here, you will enjoy lunch and a self-guided tour of the Chesapeake Bay Maritime Museum.

This afternoon’s route delivers more scenic views of the water at Claiborne Landing before returning back to St. Michael’s.

Cumulative Distance Range: 10 — 29 miles

Included Meals: Breakfast, Lunch

Leaving Easton this morning, shuttle 30 minutes to nearby Cambridge. Today’s ride starts in front of the town’s Harriet Tubman ‘take my hand’ mural.

Our scenic ride takes place in the Blackwater National Wildlife Refuge. Called one of the “Last Great Places” by the Nature Conservancy, these 32,000 acres offer quiet roadways, ideal for cycling. Established 90 years ago, this preserve was created as a haven for migrating birds and to protect endangered birds and animals. Here, nature lovers will enjoy stepping off their bikes for strolls along the marked trails through protected marshland.

You may also stop in the recently established Harriett Tubman Underground Railroad State Park, with an opportunity to tour the visitor center.

After exploring and relaxing over a picnic lunch provided by your trip leaders, you’ll shuttle to the Rock Hall and our inn, where a swim in the saltwater pool and a cool drink on the dock may be in order. Your hosts Jim and Joanne welcome us. Dinner is at the inn tonight.

Today's Ride Choices

Morning: Blackwater National Wildlife Refuge — 20 miles

What to Expect:

Your morning ride takes you to the Blackwater National Wildlife Refuge for some bird-watching. Scenic riding is on paved, quiet roadways. Stop to enjoy a picnic lunch provided by your trip leaders, and for a chance to visit the newly established Harriet Tubman Underground Railroad State Park before shuttling north to Rock Hall and our inn for the next three nights.

Cumulative Distance Range: 20 miles

Included Meals: Breakfast, Lunch, Dinner

More than half of the land in Kent County is devoted to farming. Spend the morning riding through its peaceful agricultural terrain.

Pedal past rows of wheat, corn, and soybeans on shaded lanes leading down to rewarding views of the Sassafras River and Turner’s Creek. Stop at Sassafras Natural Resources Management Area for a relaxing respite. This area is noted for its views of the Sassafras River and Chesapeake Bay from the high banks that face south. The river’s edge is an active birding area, and you may spot a mix of songbirds, waterfowl, and raptors.

Later, ride to the Crow Vineyard & Winery. This 365-acre, third-generation working farm produces award winning wines, among other things. After a tour and tasting here, shuttle back to the inn (30 minutes).

This afternoon’s ride option from the inn is a quiet one out into a peaceful wildlife refuge with views of the Chester River all around. You might want to take a walk along the wooden Tubby Cove Boardwalk which extends over the marsh to a wooded island. Once on the island, the boardwalk continues to two viewing platforms and a rough walking trail off the main path which ends at an elevated viewing platform providing vistas of Chesapeake Bay and into Tubby Cove and Calf Pasture Cove.

Dinner is on your own tonight in one of Rock Hall’s restaurants.

Today's Ride Choices

Morning: Rock Hall to Kent County — 29 or 37 miles

Afternoon: Eastern Neck Wildlife Refuge — 13 miles

What to Expect:

Today’s morning ride will take you deep into the farmland of Kent County.  Approximately 60% of the county land is devoted to a variety of crops. You’ll stop for a picnic break at Sassafras Natural Resources Management Area. After lunch, visit the Crow Vineyard & Winery for a tour and a tasting of the family’s award-winning wines. After a shuttle to the inn, the afternoon ride option takes you to the Eastern Neck Wildlife Refuge for some bird-watching. Today may offer an additional independent ride for experienced cyclists. Ask your trip leader for details.

Cumulative Distance Range: 13 — 50 miles

Included Meals: Breakfast, Lunch

After breakfast, ride north today to Chestertown, a historic colonial town on the Chester River. Chestertown was founded in 1705 and was one of Maryland’s six Royal Ports of Entry. In the mid-18th century, it was the second leading port in Maryland. The town’s shipping industry boom led to vast wealth for many of its inhabitants, evident as you pedal past the classically styled brick mansions and townhouses along the waterfront. Your VBT trip leaders will offer you a self-guided cycling tour of the historic section of Chestertown.

Continue exploring the town’s brick sidewalks visiting shops and galleries along the way. Take the time to enjoy lunch on your own at a local cafe, bakery, or one of the town’s numerous restaurants. Your VBT trip leaders will provide you with some great recommendations.

If you prefer a non-riding option, you may spend the day at the inn or enjoy browsing the charming shops and relaxing in the cafes in Rock Hall.

Tonight, we gather for a festive farewell dinner to celebrate your trip biking the Eastern Shore.

Today's Ride Choices

Morning: Inn to Chestertown — 19 miles

Afternoon: Chestertown to Inn — 14 miles

What to Expect:

Today’s ride is in the country. Cycle along quiet roads surrounded by farmland into Chestertown, a historic colonial town on the Chester River. Once there, enjoy lunch on your own and explore the town.  You have the option of taking a self-guided architectural tour by foot or by bike. Your leaders can provide you with a locally-produced map and brochure.  After your exploration, cycle back to the inn or shuttle back with your leaders in the van. Today may offer an additional independent ride for experienced cyclists. Ask your trip leader for details.

Cumulative Distance Range: 19 — 33 miles

Included Meals: Breakfast, Dinner

Your Eastern Shore biking vacation concludes mid-morning at the inn. Your included shuttle will take you back to Baltimore-Washington International Airport (BWI), arriving around 12:00 p.m. We suggest a flight out of BWI no earlier than 2:00 p.m.

Included Meals: Breakfast

Maryland: Eastern Shore & Chesapeake Bay

Download PDF Itinerary:

Tour Only (PDF)


90 out of 94 (95%)
4.6 out of 5 stars.
Read More Reviews

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.

, Michigan

Biking Chesapeake Bay Area

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.

Sandy P, Orange County, CA

The West Coast Review

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