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Biking Vacation Cape Cod & Martha's Vineyard​

Activity Level: Easy  |  Daily Mileage: 18 – 58 mi  |  Daily Biking: 2 – 4 1/2 hr
Land only
6 days from only
Pre-trip Extension:
Boston · 2 nights $345

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Detailed Itinerary

Day 1 - Arrive in Chatham, Cape Cod

Travel to Cape Cod and the Bradford Inn. If you're flying to Massachusetts, VBT will offer a shuttle from Boston's Logan International Airport. The shuttle works on a “show and go” basis and will make its only departure from the airport to the inn at 12:30 pm. Shuttle reservations are not required or available. Meet the driver outside Terminal C, on the second level, at the second island out. Your shuttle bus will carry “Access Express” titles, and the driver will be holding a VBT sign. Please allow for traffic delays.

If you are scheduled to arrive at the airport after 12:30 pm or are delayed, please take a taxi or bus at your own expense. VBT does recommend that guests try to arrange their arrival at Logan International Airport prior to 12:30 pm, as Chatham is approximately an hour and 45 minutes from Boston. If you are delayed or your travel plans change, please contact the first inn; 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 Chatham while on tour. You can park at the Bradford Inn while a guest at the inn. When you leave Chatham, the leaders will help you with the transfer of your vehicle to another location, where you may leave it while you're on Martha's Vineyard. You may return to this location at the end of the tour by way of the VBT van. We will shuttle to Woods Hole on Tuesday to ferry onto Martha's Vineyard. If you'd like to park your car in Woods Hole at the ferry terminal and avoid the shuttle back to Chatham at the end of the tour, the cost will be approximately $12 per day. Shuttle time is approximately one hour and 30 minutes.

VBT Pre-Trip Extension guests: You have another morning to enjoy Boston. At 12:50 pm, a shuttle will meet and transfer you to The Bradford Inn. Please wait for the shuttle at the corner of the Fairmont Battery Wharf's drive and Commercial Street. Your shuttle bus will carry “Access Express” titles, and the driver will be holding a VBT sign. The shuttle will be coming from Logan International Airport with other VBT guests. Please allow for traffic delays.

The tour begins at our Cape Cod hotel, the Bradford Inn, located in Chatham, Massachusetts. After settling in, meet your Trip Leaders at 3:30 pm for a safety and bike-fitting session, followed by a short warm-up ride and introduction to Chatham. Check in is at 4:00 pm. Your room may be ready earlier; please confirm with the front desk upon arrival. Later, join your fellow travelers over a wine and cheese reception, followed by dinner at the nearby Wild Goose Tavern.

Day 2 - Cape Cod Rail Trail / Cape Cod National Seashore

Our morning cycle takes us from the inn to join the Old Colony Rail Trail and the Cape Cod Rail Trail. The Cape Cod Rail Trail follows a former railroad passage for 25 miles through the towns of Dennis, Harwich, Brewster, Orleans, Eastham, and Wellfleet. Its paved surface, few hills, and well-marked automobile crossings make it ideal for biking.

Much of today's riding is through the protected Cape Cod National Seashore. We'll stop en route at the Salt Pond Visitor Center in Eastham. This is Cape Cod National Seashore's main visitor facility, with frequent orientation movies, a well-stocked bookstore, and a comprehensive museum. Offering breathtaking views of Nauset Marsh, this visitor center is also convenient to the popular 1.5-mile Nauset Marsh Trail and the Buttonbush Trail.

After lunch, choose between riding or shuttling back to Chatham, or continue on to visit Coast Guard Beach, Three Sisters Lighthouses, and Nauset Light Beach. We'll return to Chatham mostly along the bike path with some secondary road riding, or choose to continue cycling to the southern tip of Cape Cod Bay and take in a breathtaking view of the Tidal Flats at First Encounter Beach.

Back in Chatham, relax around the inn's swimming pool, stroll the village's beaches, or explore the town with its variety of shops. There are a number of great restaurant options for dinner on your own tonight. Your Trip Leaders will be happy to help with recommendations.

Day 3 - Ferry to Martha's Vineyard / Oak Bluffs / Edgartown / Chappaquiddick Island

After breakfast, we shuttle to Woods Hole and board a ferry to Martha's Vineyard. “The Vineyard,” as locals know it, is New England's largest island (23 miles long by 9 miles wide). Under the protective arm of Cape Cod, the cold Labrador Current is warded off, while waters warmed by the Gulf Stream flow up from the south. We will be able to stretch our legs on the way to Oak Bluffs via East Chop Lighthouse. Once there, we will have free time in Oak Bluffs to have lunch and explore the small town. 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! Afterwards, we'll ride along the State Beach bike path to Edgartown and our Martha's Vineyard hotel for the next three nights, the Harbor View Hotel & Resort. 

If you'd like a few more miles of riding, board the “Chappy” ferry for a three-minute sail across the 300-yard-wide strait separating Martha's Vineyard from Chappaquiddick Island. Having short trips and no timetable, the Chappaquiddick Ferry is always on time! The island's main attractions are, of course, the infamous Dike Bridge, along with the Mytoi Japanese Garden. 

Later, we return to the inn, settle into our rooms, and perhaps take a swim in the heated pool before our included dinner at one of Edgartown's local favorite and celebrated restaurants.

Day 4 - Vineyard Haven / Art galleries & crafters

After breakfast, we will ride out of Edgartown toward Vineyard Haven along the bike path. Along our route, we'll have a chance to explore Vineyard Haven, Martha's Vineyard's only year-round port of entry, before continuing on an epic cycling loop to West Chop Lighthouse and Lambert's Cove Road. As we cycle along the Island's interior, your Trip Leaders will point out lunch options in between visits to Chilmark Pottery, Martha's Vineyard Glassworks, Polly Hill Arboretum, the Field Gallery, and the Granary Gallery. The Granary Gallery boasts the most amazing paintings, sculptures, and photography from more than 300 of the island's most celebrated artisans. 

After lunch, we'll 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, this forest is a 5,000-acre pine and scrub oak area crisscrossed with hiking trails.

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

Day 5 - Menemsha / Aquinnah Cliffs

Today, we will be heading “up island.” The term comes from sailing days, when a vessel was running “up” its longitude when it was sailing west away from the prime meridian. In a similar manner, a ferry always comes “up” from Nantucket. 

Today's ride will be all the way 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 at Aquinnah are a mile long and are sprinkled with tropical fossils. The Aquinnah lighthouse stands atop the cliffs, creating a very dramatic view. The beaches below are a delightful spot to picnic and swim. 

Along the way, we'll ride through the fishing village of Menemsha. Used as the setting for the film Jaws, the area continues to serve as a working fishing port and as home to the U.S. Coast Guard. A convenient and fun seasonal bike ferry connects Menemsha with Aquinnah.

Day 6 - Ride to Katama Beach / Depart

After breakfast, we'll offer an early-morning ride to Katama Beach. Also known as South Beach, we'll enjoy three miles of barrier beach on the South Shore of the island. 

After returning to the hotel for a shower and to check out, we will transfer to Vineyard Haven for an included lunch. All aboard! Our Steamship Authority ferry leaves for a 45-minute crossing to Woods Hole. A shuttle from Woods Hole Ferry Terminal to Logan International Airport will be provided with a departure time from Woods Hole at 3:30 pm. We recommend a flight out of Boston no earlier than 7:00 pm.

If you parked your car at the start of the tour, the VBT van will transfer you back to Chatham to collect it.

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