Maryland Eastern Shore & Chesapeake Bay Bike Tour

Day One

Upon your arrival at Baltimore-Washington International Airport, you’ll be taken to the Tidewater Inn in Easton, Maryland. Here you will meet your fellow riders and trip leaders and be fitted for your bike. After a short warm-up ride, enjoy a welcome reception and 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.

Day Two

Today, experience a ride along the Oxford/St. Michaels Loop, considered one of the premiere biking routes on the East Coast. Ride through Oxford, a 17th-century town with a long tradition of boat building. From Oxford, be carried across the Tred Avon River aboard the modest Oxford-Bellevue ferry, the oldest privately owned ferry still in operation in America. 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. The skipper, Captain Ed, has spent more than 35 years dredging oysters and sailing skipjacks and his boat is a broad-beamed former working skipjack. 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. If you choose, increase your ride total by riding toward Tilghman Island from St. Michaels after lunch before backtracking to St. Michaels. This evening, explore Easton and enjoy dinner on your own. 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.
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 to St. Michael’s.
Cumulative Distance Range: 10 — 29 miles

Day Three

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. Today’s 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 provided picnic lunch, 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. 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 birdwatching. 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

Day Four

This morning, enjoy riding through the beautiful farmland of Kent County. 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. You may choose 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 birdwatching. Today may offer an additional independent ride for experienced cyclists. Ask your trip leader for details.
Cumulative Distance Range: 13 — 50 miles

Day Five

After breakfast, ride north 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. 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. 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, 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. 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.
Cumulative Distance Range: 19 — 33 miles

Day Six

Your Eastern Shore biking vacation concludes mid-morning at the Inn. An included shuttle will take you back to Baltimore-Washington International Airport (BWI).

FB=Full Breakfast, L=Lunch, D=Dinner