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Maryland: Eastern Shore & Chesapeake Bay

The lure of the sea runs deep in Chesapeake Bay; a rising tide of maritime traditions, close-knit communities, distinctive cuisine, and protected seashores, marshes, and coastal islands, all of which make for a spectacular trip biking the Eastern shore. The towns and villages of Maryland’s bay region have been home to generations of dedicated fishermen, craftspeople, and culinary artisans who provide a warm welcome to visitors. From the elegant 18th-century brick mansions to the weathered crab shacks by tidal ponds, you’ll experience the warm glow of daily life in a way only possible on bike and on foot. This active vacation features an exceptional bicycling landscape, delicious food, and warm and friendly people.

Tour Highlights

  • Sail the eastern shores with Captain Ed aboard the skipjack HM Krentz
  • Feast on the region’s famous seafood
  • Amble the wooden boardwalk at the Eastern Neck National Wildlife Refuge, a haven for more than 240 bird species
  • Travel on the country’s oldest privately owned ferry (since 1760), across the Tred-Avon River between Oxford and Bellevue
  • Cycle the quite country roads leading to the charming small towns of Oxford, St. Michaels, Rock Hall and Easton

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 the support vehicle, 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 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 Check
11 meals: 5 breakfasts, 3 lunches, 3 dinners Check
Transportation from Baltimore/Washington International Airport to Easton Check
Transportation from Rock Hall to Baltimore/Washington International Airport Check

Road Bicycle (Carbon frame)

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Step-Through Electric-Assisted Bicycle (E-bike) 1

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

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Step-Through (Mixte Hybrid) Comfort Bicycle

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Step-Over (Diamond) Comfort Bicycle

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Biking Packages Include:

Custom VBT Bike and Helmet

Two Local, Bilingual Trip Leaders

Vehicle Support

Luggage Transfers

Ride with GPS and Daily Route Notes

Welcome Reception

Facilitated Cultural Experiences

Your Choice of VBT Branded Gear for Your Adventure


Sun, Jun 5 to Fri, Jun 10 - 2022

Show Itinerary:

Travel to Easton and the Tidewater Inn. If you’re flying to Baltimore, VBT will offer a shuttle from Baltimore-Washington International Airport (BWI). The shuttle will make its only departure from the airport to the inn at 1:00 p.m., departing from the Lower-Level (baggage claim). Exit door 4 or 6, these doors are near Southwest baggage carousel 6. After exiting cross, the inner roadway. Your shuttle will be at the curb. Your Chesapeake Chauffeur Transportation driver will be holding a VBT sign.

If you are scheduled to arrive at the airport after 1:00 p.m. 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 during the trip. You can park at the Tidewater Inn from Sunday through Thursday night. You may return to this location at the end of the tour with the VBT van.

If you are delayed or your travel plans change, please contact the first inn. They will pass your message to your VBT trip leaders.

Your group will meet at the Tidewater Inn to begin your Maryland vacation, biking the Eastern shore. After settling in, explore the village from the hotel’s central location. At 3:00 p.m., join your VBT trip leaders 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 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. Afterward, 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.

After your visit to St. Michaels, hop back on your bikes, riding the direct route back to Easton. If the ferry is not operating (as sometimes happens early or late in the season) we ride in and out of St. Michaels, including a wooded loop through the small villages of Unionville and Tunis Mills in the morning. Unionville was settled by Africa-American who served in the regular Union army during the Civil War. Tunis Mills has a wooden decked bridge where county public works built a swimming deck and ladder for the local children.

Mileage hounds may increase your ride total by riding toward Tilghman Island from St. Michaels after lunch before backtracking to St. Michaels and back to Oxford. Or take the Unionville/Tunis Mills loop on your return from St. Michaels to Easton.

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 meet for a walking tour of Easton and then you will be on your own for dinner and additional exploring. Your VBT trip leaders or your walking tour guide will be happy to give you suggestions for great local restaurants. Tomorrow night we will dine as a group at Out of the Fire, so you may want to choose a different location for dinner tonight.

Today’s Ride Choices

Morning St. Michaels to Oxford to Easton — 20 miles

Afternoon Easton to St. Michaels — 13 miles

What to Expect: The St. Michaels loop is recognized as one of the favorite bike rides in the Mid-Atlantic region. The charming, tree-lined town of Oxford is one of the oldest towns in America. 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.

Cumulative Distance Range: 13 — 33 miles

Included Meals: Breakfast, Lunch

More than half of the land in Talbot County is devoted to farming or low density residential plots, 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 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, osprey, warblers, herons, and kingfishers.

Later, ride to the sleepy town of Cordova. En route to the inn, stop for a picnic lunch and wine tasting at Triple Creek Winery. After the picnic, you may bike back to the inn or join the trip leaders in the van to shuttle back.

Tonight’s dinner is at Out of the Fire, one of Easton’s popular restaurants.

Today’s Ride Choices

Morning Easton to Talbot County — 20 miles

Afternoon Talbot County to Easton — 8 miles

What to Expect: Today’s ride will take you deep into the farmland of Talbot County. Approximately 60% of the county land is devoted to a variety of crops. You’ll ride on shaded lanes with rewarding views of the Choptank River and stop for a quick break at Kingston Landing. After the break, we ride on to our picnic lunch spot—Triple Creek Winery. After lunch, continue riding through the countryside before returning to the hotel.

Cumulative Distance Range: 8 — 28 miles

Included Meals: Breakfast, Lunch, Dinner

This morning, 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.

After the morning sail, travel by shuttle to Rock Hall and enjoy a picnic lunch before cycling the Eastern Neck Wildlife Refuge. A glorious haven for almost 250 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 which ends at an elevated viewing platform providing vistas of Chesapeake Bay and into Tubby Cove and Calf Pasture Cove. After exploring, you’ll continue your ride to the 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 on your own tonight in one of Rock Hall’s restaurants.

Today’s Ride Choices

Afternoon Rock Hall to Eastern Neck Wildlife Refuge — 15 miles

What to Expect: Your afternoon ride takes you to the Eastern Neck Wildlife Refuge for some bird-watching. After this visit to the Eastern Neck Wildlife Refuge ride to the inn to relax and enjoy the beautiful and relaxing property where you will spend the next two nights.

Cumulative Distance Range: 15 miles

Included Meals: Breakfast, Lunch

After breakfast, ride north today to Chestertown, a historic colonial town located 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. With this important designation and the resulting shipping business, the town became quite wealthy, which becomes evident as you pedal past the 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 along 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. The interactive tour is online at After your exploration, cycle back to the inn or shuttle back with your leaders in the van.

Cumulative Distance Range: 19 — 33 miles

Included Meals: Breakfast, Dinner

Your biking the Eastern shore vacation concludes after breakfast at the inn. Your included shuttle is available to 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. For guests who parked at the Tidewater Inn, a shuttle will be provided leaving the Inn at Huntingfield Creek at 10:00 a.m. arriving in Easton around 12:00 p.m.

Included Meals: Breakfast

Maryland: Eastern Shore & Chesapeake Bay 8

Download PDF Itinerary:

Tour Only (PDF)

Accommodations (May vary depending on departure date. )

44 out of 54 (81%)
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

Maryland: Cycling the Chesapeake Bay

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

Maryland: Cycling the Chesapeake Bay

Dates & Prices

Departure Date :

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6 Days. Includes bike vacation only.

Single Supplement: From $545

Sun, Jun 5 - Fri, Jun 10, 2022


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For more information, call: 800-245-3868

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