Maryland: Eastern Shore & Chesapeake Bay

Your Maryland biking adventure begins at the Tidewater Inn, centrally located in the charming village of Easton. If you’re flying to Baltimore, VBT offers a complimentary shuttle from Baltimore-Washington International Airport (BWI). The shuttle will make its only departure at 1:00 p.m. from the airport to the inn.

After settling in, take some time to explore the town. At 3:00 p.m., meet your VBT trip leaders for a safety and bike-fitting session, followed by a short warm-up ride. Then, join your fellow travelers at 5:30 p.m. for an orientation and welcome reception, followed by an included dinner at 7:00 p.m. in the inn’s restaurant.

Today's Ride Choices

Afternoon: Easton Warm-Up Ride — 6 miles

What to Expect:

Your warm-up ride offers a chance to get acquainted with the bicycle that will be your trusted companion for the week. Depart from the Tidewater Inn and enjoy a relaxed spin along the quiet Easton Rails-to-Trails path.

Cumulative Distance Range: 6 miles

Included Meals: Dinner

Today you’re in for a treat—the Oxford/St. Michaels Loop is considered one of the premier biking routes on the East Coast. Your clockwise ride begins at your inn and leads through Oxford, a 17th-century town with a rich boatbuilding heritage. Just two blocks from our rest stop, you’ll find Cutts and Case Boatyard, home to a number of classic wooden boats on display.

Next, board the modest Oxford-Bellevue Ferry—the oldest privately owned ferry still in operation in America—for a short crossing of the Tred Avon River. From Bellevue, cycle through the charming town of Royal Oak, then continue on to St. Michaels, a picturesque bayside town, where you’ll enjoy an included lunch.

In the afternoon, depending on availability, you’ll either sail aboard the HM Krentz, a working sail-powered skipjack, or board a former U.S. Navy launch turned cruiser for a captain-guided orientation to the Chesapeake Bay Estuary. You’ll also have time for a self-guided tour of the outstanding Chesapeake Bay Maritime Museum, which features over ten exhibit buildings, the 1879 Hooper Strait Lighthouse, a working boatyard, and the world’s largest collection of Bay boats. St. Michaels is also ideal for browsing shops, snacking, and soaking up the lively atmosphere.

Mileage hounds can extend their ride by cycling toward Tilghman Island before looping back to St. Michaels.

Back in Easton—a town often featured on “best small towns in America” lists—you’ll find a delightful mix of dining, antique shops, galleries, and stores. The Tidewater Inn, a village centerpiece since 1712, offers fine food and drink at Hunter’s Tavern.

This evening, dinner is on your own. Your VBT trip leaders will be happy to offer recommendations for excellent local restaurants.

Today's Ride Choices

Morning: Easton to St. Michaels — 19 miles OR Tunis Mills to Easton — 11 miles

Afternoon: St. Michaels to Claiborne Landing to St. Michaels — 10 miles

What to Expect:

The St. Michaels Loop is recognized as one of the premier bike trails in the Mid-Atlantic region, leading to the charming and popular bayside town of St. Michaels, where you’ll enjoy lunch and a self-guided tour of the Chesapeake Bay Maritime Museum. This afternoon’s route offers additional scenic waterfront views before looping back to St. Michaels.

Cumulative Distance Range: 10 — 30 miles

Included Meals: Breakfast, Lunch

Leaving Easton this morning, you’ll shuttle about 30 minutes to nearby Cambridge. Today’s ride begins in front of the town’s iconic Harriet Tubman “Take My Hand” mural.

Your scenic route winds through Blackwater National Wildlife Refuge. Recognized by The Nature Conservancy as one of the “Last Great Places,” this 32,000-acre preserve offers quiet roadways ideal for cycling. Established 90 years ago, it serves as a haven for migrating birds and a sanctuary for endangered species. Nature lovers may enjoy stepping off their bikes to stroll along marked trails through the protected marshland.

You may also choose to visit the Harriet Tubman Underground Railroad State Park and explore the informative exhibits at the visitor center.

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

Today's Ride Choices

Morning: Blackwater National Wildlife Refuge — 20 miles

What to Expect:

Your morning ride takes you through the Blackwater National Wildlife Refuge for some peaceful bird-watching. Enjoy scenic cycling along paved, quiet roadways. Pause for a picnic lunch provided by your trip leaders and take time to visit the newly established Harriet Tubman Underground Railroad State Park. In the afternoon, shuttle north to Rock Hall and settle in at 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, and this morning’s ride takes you through its peaceful agricultural terrain.

Pedal past rows of wheat, corn, and soybeans on shaded lanes leading to rewarding views of the Sassafras River and Turner’s Creek. Stop at the Sassafras Natural Resources Management Area for a relaxing break. This area is known for its sweeping views of the Sassafras River and Chesapeake Bay from high banks facing south. The river’s edge is a haven for birdwatchers, with potential sightings of songbirds, waterfowl, and raptors.

Later, ride to Crow Vineyard & Winery, a 365-acre, third-generation working farm that produces award-winning wines. Enjoy a tour and tasting before shuttling back to the inn (approximately 30 minutes).

This afternoon, an optional ride from the inn leads into a tranquil wildlife refuge with views of the Chester River. Consider a walk along the Tubby Cove Boardwalk, which stretches over the marsh to a wooded island. The boardwalk continues to two viewing platforms and a rough walking trail that ends at an elevated platform offering panoramic views of Chesapeake Bay, Tubby Cove, and Calf Pasture Cove.

Dinner is on your own this evening at one of Rock Hall’s inviting 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:

This morning’s ride takes you deep into the farmlands of Kent County, where approximately 60% of the land is devoted to a variety of crops. Stop for a picnic break at the Sassafras Natural Resources Management Area before continuing to Crow Vineyard & Winery for a tour and tasting of the family’s award-winning wines. After a shuttle back to the inn, an optional afternoon ride leads to the Eastern Neck Wildlife Refuge for scenic bird-watching. Today may also offer an additional independent ride for experienced cyclists—ask your trip leaders for details.

Cumulative Distance Range: 13 — 50 miles

Included Meals: Breakfast, Lunch

After breakfast, ride north to Chestertown, a historic colonial town on the Chester River. Founded in 1705, Chestertown was one of Maryland’s six Royal Ports of Entry and, by the mid-18th century, the second leading port in the state. The town’s shipping boom brought great wealth, evident as you cycle past stately brick mansions and townhouses along the waterfront. Your VBT trip leaders will provide a self-guided cycling tour of Chestertown’s historic district.

Continue exploring the town’s brick sidewalks, visiting shops and galleries along the way. Enjoy lunch on your own at a local café, bakery, or one of the many restaurants—your trip leaders will offer recommendations.

If you prefer not to ride today, you may relax at the inn or explore the charming shops and cafés of Rock Hall.

This evening, gather for a festive farewell dinner to celebrate your journey 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 takes you along quiet country roads through scenic farmland en route to Chestertown, a historic colonial town on the Chester River. Upon arrival, enjoy lunch on your own and take time to explore. You may opt for a self-guided architectural tour—on foot or by bike—using a locally produced map and brochure provided by your trip leaders. After your visit, cycle back to the inn or return by van with your leaders. Today may also offer an additional independent ride for experienced cyclists; ask your trip leaders for details.

Cumulative Distance Range: 19 — 33 miles

Included Meals: Breakfast, Dinner

Your Eastern Shore biking vacation concludes mid-morning at the inn. An included shuttle will return you to Baltimore-Washington International Airport (BWI), arriving around 12:00 p.m. We recommend scheduling your flight no earlier than 2:00 p.m.

Included Meals: Breakfast

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.

We either sail on the HM Krentz, a working sail-powered skipjack, or board a former US Navy Launch turned cruiser, and are treated to a Captain-guided orientation to the Chesapeake Bay Estuary, depending on availability.

There is also 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. Michaels — 19 miles OR Tunis Mills to Easton — 11 miles

Afternoon: St. Michaels to Claiborne Landing to St. Michaels — 10 miles

What to Expect:

The St. Michaels 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 before returning back to St. Michael’s.

Cumulative Distance Range: 10 — 30 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