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Maryland: Cycling the Chesapeake Bay

Cycle in a small group and experience the very soul of the Chesapeake Bay through its maritime tradition, close-knit communities, protected seashores, and regional cuisine as distinctively flavorful as any in the world.

  • Activity Level: Easy
  • Daily Mileage: 13 - 32 mi
  • Daily Biking: 2 - 4 1/2 hr
  • Small Groups: 20
  • Biking
  • Easy

Why You'll Love This Tour


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.

Cultural Highlights

  • 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

Climate Information

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

What’s Included:

  • 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
  • Daily route directions and maps
  • Welcome reception
  • Sightseeing and cultural activities
  • Transfers
  • 5% Frequent Traveler Credit to use on your next VBT vacation
  • Special Good Buy Discount
Dates & Prices
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Departure: Sunday, October 23
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Land Only Single Supplement: $495

Please note: Web Special savings cannot be combined with any other offer. Standard Terms & Conditions apply when purchasing this trip. 2016 Prices include all airline surcharges and Government taxes and fees. Ask our Tour Consultants for details. Every effort has been made to produce this information accurately. We reserve the right to correct errors. Prices are based on preferences selected above, including meals and sightseeing as specified in What’s Included. All prices are subject to change. Departure dates and prices shown may be updated several times daily, and apply to new bookings only.

Itinerary & Map
Or, Expand All Days
DAY 1: Arrive Easton / Warm-up ride / Welcome reception

Make your own arrangements for travel to Maryland. If you’re flying to Baltimore, VBT will offer a shuttle from the Baltimore-Washington International Airport (BWI). The shuttle works on a “show and go” basis and will make its only departure from the airport to the inn at 1:00 pm. Shuttle reservations are not required or available. The shuttle will depart from the lower level, the baggage claim level, at Door 10 on the inner roadway. Your shuttle bus will carry “GO The Airport Shuttle” titles, and the driver will be holding a VBT sign.

If you are scheduled to arrive at the airport after 1:00 pm or are delayed, you must take a taxi or bus at your own expense. If you are driving to the tour, we recommend that you leave your vehicle in Easton while on tour. You can park at the Tidewater Inn while on tour (Sunday through Thursday nights inclusive). You may return to this location at the end of the tour by way of the VBT van.

If you are delayed or your travel plans change, please contact the Tidewater inn at 410.822.1300; they will pass your message to your VBT Trip Leaders.

Our group meets at the Tidewater Inn to begin our Maryland vacation. After settling in, explore the village from the hotel’s central location. At 3:00 pm, join your VBT Trip Leaders for a safety and bike-fitting session, followed by a short warm-up ride. At 5:00 pm, meet up with the group for an orientation and welcome reception before a 7:00 pm dinner at the inn.

Hotel: Tidewater Inn
Meals: D
Daily Options: 6 miles

DAY 2: Ride the Oxford & St. Michaels Trail / Lunch in St. Michaels / Guided visit to the Chesapeake Bay Maritime Museum

Today you are in for a treat. The Oxford/St. Michaels loop is considered one of the premiere biking routes on the East Coast. We’ll ride counter-clockwise from our inn, stopping for an included lunch in St. Michaels, a small bayside town on a long, narrow neck of land. Afterward, our group will have a self-guided tour of the impressive Chesapeake Bay Maritime Museum. The museum comprises more than ten exhibit buildings, the 1879 Hooper Strait Lighthouse, a working boatyard, and the world’s largest collection of Bay boats. Plus, St. Michaels offers wonderful shopping, snacking, and plenty of people-watching opportunities.

After our visit in St. Michaels, we’ll hop back on our bikes, riding through Royal Oak to reach Bellevue. Upon arrival, we’ll board the modest Oxford-Bellevue ferry, the oldest privately owned ferry still in operation in America. After crossing, we’ll be in Oxford. Worth a visit, this 17th-century town has a long tradition of boat building. If you want to stop for homemade ice cream, The Scottish Highland Creamery is the place for it.

After your mid-afternoon ice cream treat, we’ll continue riding back to our inn. Easton has been featured on many “best small towns in America” lists. The village is small in scale, but packed with great dining options, antiques, galleries, and shopping. Our comfortable inn has played a central role in the village since 1712. Recently renovated, it features great eating and drinking at Hunters’ Tavern.

For dinner, choose from one of the fine restaurants in town.

Hotel: Tidewater Inn
Meals: B, L
Daily Options: 13 or 18 miles

DAY 3: Ride the farmlands of Talbot County / Cordova / Wine Tasting

More than half of the land in Talbot County is devoted to farming, and we’ll spend the morning riding through its wide-open fields and pastures.

We divert from the rows of wheat, corn, and soybeans, riding on shaded lanes leading down to rewarding views of the Choptank River. Stop at Kingston Landing for a relaxing respite. The river’s edge is an active birding area, and you may spot Bald Eagles, Yellow-throated Warblers, or Indigo Buntings.

Later, we’ll ride on to the sleepy town of Cordova. You might enjoy exploring the town’s two general stores before we turn west, riding back toward Easton. En route to our inn, we’ll stop for a picnic lunch on the grounds of a family-run winery. After our picnic, enjoy a tasting of our hosts’ wines.

Tonight’s dinner is at one of Easton’s popular restaurants.

Hotel: Tidewater Inn
Meals: B, L, D
Daily Options: 19 or 27 miles

DAY 4: Sail to Rock Hall / Eastern Neck Island National Wildlife Refuge

This morning, we board the HM Krentz for a sail north through the Kent Narrows to Rock Hall. Our skipper, Captain Ed, has spent more than 35 years dredging oysters and sailing skipjacks for his livelihood, and his boat is a broad-beamed former working skipjack. Her stable decks are perfect for catching the sea air.

Upon arrival in Rock Hall, we’ll enjoy a picnic lunch before cycling to the Eastern Neck Wildlife Refuge. A glorious haven for more than 240 bird species, 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 ends at an elevated viewing platform that provides vistas of Chesapeake Bay and into Tubby Cove and Calf Pasture Cove. After exploring, we’ll continue our ride to the inn, where our hosts Jim and Joanne welcome us, and a swim in the pool and a cool drink on the dock may be in order. Dinner is on your own tonight in one of Rock Hall’s restaurants.

Hotel: Inn at Huntingfield Creek
Meals: B, L
Daily Options: 14 miles

DAY 5: Ride to Chestertown

We’ll ride north today to Chestertown, a historic colonial town located on the Chester River. Chestertown was founded in 1705 and was once one of Maryland’s six Royal Ports of Entry. In the mid-18th century, it was the second leading port in Maryland. With this important designation and the resulting shipping business, the town became quite wealthy, as heralded by the brick mansions and townhouses along the waterfront. Your leaders will offer you a self-guided cycling tour of the historic section of Chestertown.

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

If you prefer a non-riding option today, 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 to celebrate with a festive farewell dinner.

Hotel: Inn at Huntingfield Creek
Meals: B, D
Daily Options: 18 or 35 miles

DAY 6: Depart for home

Our tour concludes after breakfast at our inn. Our included shuttle is available to take you back to the Baltimore-Washington International Airport (BWI), arriving around 12:00 pm. We suggest a flight out of BWI no earlier than 2:00 pm. We will shuttle guests who have cars parked at the Tidewater Inn. This shuttle will arrive at the inn around 12:00 pm.

Meals: B
Daily Options: non-riding day

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Inn at Huntingfield Creek

The Inn at Huntingfield Creek is a 70-acre refuge in the finest Chesapeake tradition. Hosts Jim and Joanne Rich each bring business and life experiences together to create wonderful memories at this quiet, country retreat. Our group will have exclusive use of the inn during our stays. Enjoy the swimming pool, the piano in the living room, and the sunset views from the dock over the tidal waterfront. This is the perfect setting from which to venture out on our planned activities.
Free WiFi Included

Tidewater Inn

Accommodations at the Tidewater Inn offer the best of both worlds: the tranquility and charm of a historic Colonial inn along with the modern luxuries today’s traveler has come to expect. Traditional decor and furnishings offer the perfect reflection of our historic downtown Easton setting, while resort-style amenities make for an indulgent stay. Relax in plush bedding featuring pillow-top mattresses under a cascade of fine European linens. Wrap yourself in a downy Egyptian cotton robe. Enjoy tech-savvy touches like flat-screen televisions and high-speed Internet access.
Free WiFi Included

Maryland Bike Tour Photo Gallery
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