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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|
  • Biking: 1 - 6 hr|
Activity Easy Easy
Cycling
Bar Graph Beginner - Experienced
Cyclists
Vehicle Support Vehicle
Support

Average High /
Low Temperature (°F):

Apr67º/48º

May75º/57º

Jun70º/41º

Sep67º/37º

Oct71º/53º

Average
Precipitation:

Apr2.9 in

May3.5 in

Jun1.5 in

Sep1.3 in

Oct3.4 in

Tour Only

5 nights in charming country inns Check
11 meals: 5 breakfasts, 3 lunches, 3 dinners 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

Itinerary

Sun, Apr 10 to Fri, Apr 15 - 2022

Show Itinerary:

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 Choice

Afternoon: Warm-up Chatham 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
Accommodation: Tidewater Inn, Easton
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 counter-clockwise route from your inn, 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 of. 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 through Royal Oak to reach Bellevue. Upon arrival, board the modest Oxford-Bellevue ferry, the oldest privately owned ferry still in operation in America. You’ll arrive in Oxford, a 17th-century town with a long tradition of boat building. Don’t forget to stop for homemade ice cream at the Scottish Highland Creamery.

After your mid-afternoon ice cream delight, continue back to the inn. 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: Easton to St. Michael’s – 13 miles
Afternoon: St. Michael’s to Oxford to Easton – 20 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 takes you through the charming, tree-lined town of Oxford, one of the oldest towns in America.

Cumulative Distance Range: 13 – 33 miles
Accommodation: Tidewater Inn, Easton
Included Meals: Breakfast, Lunch

More than half of the land in Talbot 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 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, and indigo buntings.

Later, ride to the sleepy town of Cordova. You might enjoy exploring the town’s two general stores before turning west back toward Easton. 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. In Cordova, you can visit the town’s two general stores before continuing 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
Accommodation: Tidewater Inn, Easton
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
Accommodation: Inn at Huntingfield Creek, Rock Hall
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. 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.

Cumulative Distance Range: 19 – 33 miles
Accommodation: Inn at Huntingfield Creek, Rock Hall
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

Reviews

Guest Reviews 25 out of 29 (86%) of reviewers recommend this tour

4.6 out of 5 stars.

Dates & Prices

Tour Only

6 Days. Includes bike vacation only.

Single Supplement: From $545

Sun, Apr 10 - Fri, Apr 15, 2022

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$1,995

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Sun, Apr 17 - Fri, Apr 22, 2022

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$2,345

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Sun, Apr 24 - Fri, Apr 29, 2022

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Sun, May 1 - Fri, May 6, 2022

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$2,395

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Sun, May 8 - Fri, May 13, 2022

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Sun, May 15 - Fri, May 20, 2022

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Sun, May 22 - Fri, May 27, 2022

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Sun, May 29 - Fri, Jun 3, 2022

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Sun, Jun 5 - Fri, Jun 10, 2022

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Sun, Sep 4 - Fri, Sep 9, 2022

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Private Group

Sun, Sep 11 - Fri, Sep 16, 2022

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Sun, Sep 18 - Fri, Sep 23, 2022

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Sun, Sep 25 - Fri, Sep 30, 2022

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Sun, Oct 2 - Fri, Oct 7, 2022

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Sun, Oct 9 - Fri, Oct 14, 2022

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Sun, Oct 16 - Fri, Oct 21, 2022

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For more information, call: 800-245-3868

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