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Massachusetts: Cape Cod & Martha’s Vineyard

Coastal forests, breathtaking seashores, rolling farm fields, and colorful cliffs frame your Cape Cod and Martha’s Vineyard bike adventure. Cycle the Cape’s famous Rail Trail to scenic lighthouses, and through Martha’s Vineyard’s gingerbread cottages, artists’ colonies, and tranquil beaches. Along the way, serene marshes, sweeping dunes, lush lagoons, and breathtaking shores greet you at every turn. Enjoy a picnic feast in the Cape Cod Seashore National Park. Ride through the Manuel F. Correllus State Forest, a 5,000-acre pine and scrub oak forest crisscrossed with hiking trails. In Menemsha—a working fishing port and setting of the film Jaws—absorb the seaside ambiance. And from the brilliantly colored Aquinnah Cliffs, revel in panoramic view of the sea stretched out before you.

Tour Highlights

  • Enjoy the lovely vistas along the Cape Cod Rail Trail
  • Stop at Salt Pond Visitors Center for views of Nauset Marsh and a lesson on natural habitats
  • Pause for a picnic lunch along the Cape Cod National Seashore
  • Savor a tour and cheese tasting at The Grey Barn and Farm in West Tisbury
  • Take a spin on the Vineyard’s State Beach bike path
  • Browse the handicrafts of Vineyard Haven’s wonderful artisans
  • Cycle the pastoral pathways of Correllus State Forest on a dedicated bike path
  • Pedal along the soaring Aquinnah cliffs and through the Menemsha fishing village
  • Visit the Mytoi Japanese Garden on Chappaquiddick Island
  • Ferry across the Vineyard Sound
  • Walk the grounds of Martha’s Vineyard’s Polly Hill Arboretum

What to Expect

This tour offers mostly easy terrain with the occasional rolling hill and the opportunity for some longer moderate rides. Our VBT van support shuttle is always available throughout the trip. During peak season, roughly July 1 to August 25, there is more traffic on the Cape and Islands, but you will get to experience the best weather and have the opportunity to explore lively bike paths, beaches, shops, and restaurants.

  • Daily Mileage: 8 - 57|
  • Biking: 1 - 6 hr|
Activity Easy Easy
Bar Graph Beginner - Experienced
Vehicle Support Vehicle

Average High /
Low Temperature (°F):








May3.55 in

Jun3.51 in

Jul3.1 in

Aug3.96 in

Sep3.48 in

Oct3.95 in

Tour Only

2 nights at a renowned resort and 3 nights in a quintessential island inn Check
10 meals: 5 breakfasts, 2 lunches, 2 dinners Check

Step-Through (Mixte Hybrid) Comfort Bicycle

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Step-Over (Diamond) Comfort Bicycle

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Road Bicycle (Aluminum alloy frame)

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Electric-Assisted Bicycle (E-bike)

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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, Sep 26 to Fri, Oct 1 - 2021

Show Itinerary:

Travel to Cape Cod and the Chatham Bars Inn. If you’re flying to Massachusetts, VBT offers a shuttle from Boston’s Logan International Airport. The shuttle works on a “show and go” basis with no reservations accepted and will leave the airport at 12:30 p.m. Meet the driver outside Terminal C, on the upper (second) level, at the second island out. Your shuttle bus will be a black executive mini-coach, and the driver will be holding a VBT sign.

If you are scheduled to arrive at the airport after 12:30 p.m. or are delayed, you will need to take a taxi or bus at your own expense. VBT recommends that guests try to arrange their arrival at Logan International Airport prior to 12:30 p.m. as Chatham is approximately an hour and 45 minutes from Boston (traffic permitting). If you are delayed or your travel plans change, please contact the resort; they will pass your message on to your VBT trip leaders. If you are driving to the Cape, we recommend that you leave your vehicle in a lot at the Chatham Bars Inn while there. You will need to move your car to Woods Hole at the remote parking lot near the ferry terminal on Day 3 of the tour. The cost will be approximately $15-$20 per day.

Your Cape Cod bike tour begins at our Cape Cod accommodations, Chatham Bars Inn, located in Chatham. Meet your trip leaders at 3:30 p.m. for a safety and bike-fitting session, followed by a warm-up ride and introduction to the area. Your short jaunt will give you your first views of the Atlantic Ocean at the Chatham Lighthouse & Coast Guard Station. Please come dressed to cycle or have your cycling clothes accessible in a separate bag or daypack. We will have time to settle into your rooms following the bike-fitting and warm-up ride.

Check in is at 4:00 p.m., but your room may be ready earlier. This evening, join your fellow travelers for a welcome reception, followed by dinner at the inn.

Accommodation: Chatham Bars Inn, Chatham
Included Meals: Dinner

Today’s Ride Choice:
Cumulative Distance Range: 7.5 miles
Warm-up Chatham: 7.5 miles

What to Expect: Your warm-up spin gives you the opportunity to get acquainted with the bicycle that will be your stalwart companion for the week. You will follow gentle terrain passing Chatham Lighthouse Beach to the Monomoy National Wildlife Refuge. Continue past the harbors of South Chatham before returning to the hotel through the village—your first introduction to Chatham’s quaint Main Street.

This morning, your route takes you from the resort to the Cape Cod Rail Trail. The rail trail follows a former railroad passage to the Outer Cape. The paved surface, few hills, and well-marked automobile crossings make it ideal for biking.

Much of today’s Cape Cod bike route runs through the protected Cape Cod National Seashore. You’ll stop at the Salt Pond Visitor Center in Eastham (opening times subject to seasonal availability). This is Cape Cod National Seashore’s primary visitor center, with frequent orientation movies, a well-stocked bookstore, and a comprehensive museum. Offering breathtaking views of Nauset Marsh, the center also offers convenient access to the popular 1.5-mile Nauset Marsh Trail and the Buttonbush Trail. You may extend your ride along a beautiful coastal loop, stopping at Coast Guard Beach, Nauset Light Beach, Nauset Light, and the Three Sister Lighthouses. Stop for an included picnic in the Cape Cod National Seashore National Park. Visit the historic landmark and tidal flats of First Encounter Beach, the site of the first meeting between the Native Americans and Pilgrims prior to their settling in Plymouth. Head back to reward yourself at Hot Chocolate Sparrow. You may ride or shuttle back to the inn.

Back at the resort, enjoy some free time at the hotel this evening or take a stroll into the quaint New England village of Chatham. There are great restaurant options for dinner on your own tonight. Your trip leaders will be happy to help with recommendations.

Accommodation: Chatham Bars Inn, Chatham
Included Meals: Breakfast, Lunch

Today’s Ride Choices:
Cumulative Distance Range: 9 – 57 miles
Chatham to Doane Rock Picnic Area: 29 miles
Doane Rock Picnic Area to Orleans: 9 miles
Orleans to Chatham Bars Inn: 19 miles

What to Expect: After a start on local roads, our morning ride takes the Cape Cod Rail Trail all the way to the Salt Pond Visitor’s Center on a mostly flat, paved path with clearly marked automobile crossings. The 12-mile option passes through sawgrass, sand dunes and wooded glades. Those looking for a long ride may cycle back to Chatham.

After breakfast, you’ll shuttle (approximately 1.5 hours) to Woods Hole and board a ferry to Martha’s Vineyard. (If you have driven to Chatham, you will drive your own car and park it in Woods Hole remote parking and use their complimentary shuttle service to the ferry terminal.) “The Vineyard,” as locals know it, is New England’s largest island, 23 miles long and 9 miles wide. Under the protective arm of Cape Cod, the cold Labrador Current is warded off from the island’s shores while waters warmed by the Gulf Stream flow up from the south.

Your leaders will unload your bicycle at the park upon exiting the ferry. Oak Bluffs has been a summer resort since the early 1800s, and its history is reflected in the colorful gingerbread cottages surrounding the village green. The town’s Flying Horses Carousel has been in operation since 1884. You’ll ride along the State Beach bike path to Edgartown where you will spend the next three nights. Lunch today is on your own; your leaders will offer recommendations for the best local cuisine.

If you’d like more riding time today, board the “Chappy” ferry for a three-minute sail across the 300-yard strait that separates Martha’s Vineyard from Chappaquiddick Island. With short trips and no timetable, the Chappaquiddick Ferry is always “on time.” The island’s main attractions are, of course, the infamous Dike Bridge, and the Mytoi Japanese Garden, set in a lovely pine forest.

Later, return to the inn, settle into your room, and perhaps take a swim in the heated pool. You will have many options for dinner at any one of Edgartown’s celebrated restaurants. Your trip leaders will have suggestions for you.

Accommodation: Harbor View Hotel & Resort, Edgartown
Included Meals: Breakfast

Today’s Ride Choices:
Cumulative Distance Range: 14 – 17 miles
Vineyard Haven to Edgartown: 17 miles
Oak Bluffs to Edgartown: 14 miles

What to Expect: Explore Oak Bluffs and its beloved gingerbread cottages. From Oak Bluffs, cycle into Edgartown. Once in Edgartown, take the ‘On Time’ Chappy Ferry to Chappaquiddick Island. Here you’ll want to see Mytoi Japanese Gardens and the infamous Dike Bridge.

After breakfast and a short shuttle, you’ll ride from Vineyard Haven, Martha’s Vineyard’s only year-round port of entry. Then cycle a rewarding loop to West Chop Lighthouse and Lambert’s Cove Road. As you cycle along the island’s interior, stop to visit Martha’s Vineyard Glassworks, Polly Hill Arboretum, the Field Gallery, and the Granary Gallery. The Granary Gallery boasts impressive paintings, sculptures, and photography from more than 300 of the island’s most celebrated artists.

Ride to the Grey Barn and Farm for an included cheese tasting. After a picnic lunch prepared by your trip leaders, cycle back to Edgartown by way of the paved bike path through the Manuel F. Correllus State Forest. Located in the center of the island, the park is a 5,000-acre pine and scrub oak forest crisscrossed with hiking trails.

The rest of the day and dinner are at your leisure.

Accommodation: Harbor View Hotel & Resort, Edgartown
Included Meals: Breakfast, Lunch

Today’s Ride Choices:
Cumulative Distance Range: 13 – 28 miles
Tisbury & West Tisbury: 15 miles
West Tisbury to Edgartown: 13 miles

What to Expect: Ride to Vineyard Haven, the main village of Tisbury and then on to the West Chop Lighthouse. Learn about organic farming on the Vineyard at The Grey Barn and Farm during a tour and cheese tasting, followed by a picnic lunch. Visit local artists and galleries as you ride through West Tisbury.

Today you will be heading “up island.” The term comes from sailing days, when a vessel was running “up” its longitude, sailing west, away from the prime meridian. In a similar manner, a ferry always comes “up” from Nantucket, which lies to the east of the Vineyard.

Cycle to the breathtaking Aquinnah Cliffs and beach on the western part of the island. Perhaps the best-known natural feature of the Vineyard, the brilliantly colored cliffs of Aquinnah are one mile long and filled with tropical fossils. The Aquinnah Lighthouse stands atop the cliffs, striking a very dramatic pose, and the beaches below are a delightful spot for a picnic and a swim.

Along the way, you will ride through the fishing village of Menemsha. Used as the setting for the film Jaws, the village continues to serve as a working fishing port and is home to a U.S. Coast Guard station. A fun seasonal bike ferry connects Menemsha with Aquinnah. Stop to order lunch from one of the local fish markets and find a place to sit and eat overlooking the Menemsha Basin. Enjoy some free time back at the resort or in town before your farewell celebration dinner.

Accommodation: Harbor View Hotel & Resort, Edgartown
Included Meals: Breakfast, Dinner

Today’s Ride Choices:
Cumulative Distance Range: 17 – 47 miles
Ferry Two Way – Aquinnah Cliffs: 24 miles
No Ferry – Aquinnah Cliffs: 30 miles
Return to Edgartown: 17

What to Expect: Cycle along bike paths and back roads and take a unique bike ferry to the Aquinnah Cliffs. Here you can browse the shops and visit the lighthouse. The views from the escarpment overlooking the Atlantic Ocean are magnificent. Afterward, return to the bike ferry and ride to Menemsha, the backdrop town for the classic film Jaws, and your lunch spot for today. Enjoy the return ride along the island roads through Menemsha, Chilmark, and West Tisbury and along the bike path through Manuel F. Correllus State Forest back to Edgartown.

Your Cape Cod bike journey ends after breakfast, where you may join an early-morning ride to Katama Beach, also known as South Beach, and stroll three miles of barrier beach on the South Shore of the island.

After returning to the hotel to check out, you will transfer to Oak Bluffs. Your trip leaders can recommend a spot to pick up a packed lunch for your journey back to the mainland, or you can purchase lunch on board the ferry. After a 45-minute crossing to Woods Hole, a shuttle from Woods Hole Ferry Terminal to Logan International Airport will be provided, departing Woods Hole at 1:05 p.m. We recommend a flight out of Boston no earlier than 5:00 p.m. Guests who parked their cars at the remote parking lot will board a complimentary shuttle service back to the lot.

Included Meals: Breakfast

Today’s Ride Choice:
Cumulative Distance Range: 8 miles
Katama Beach: 8 miles

What to Expect: Enjoy an early morning ride to Katama Beach. Cycle through Edgartown for one last outing to the Atlantic shore. Return your bike no later than 9:30 a.m.

Meet in the lobby for a 10:30 a.m. shuttle to Oak Bluffs for lunch on your own and a ferry back to the mainland.

Massachusetts: Cape Cod & Martha's Vineyard

Download PDF Itinerary:

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Guest Reviews 70 out of 77 (91%) of reviewers recommend this tour

4.7 out of 5 stars.

Dates & Prices

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6 Days. Includes bike vacation only.

Single Supplement: From $1,045

Currently Full

Sun, Sep 26 - Fri, Oct 1, 2021


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Currently Full

Sun, Oct 3 - Fri, Oct 8, 2021


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Currently Full

Sun, Oct 10 - Fri, Oct 15, 2021


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For more information, call: 800-245-3868

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