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Martha's Vineyard Itinerary - 7 Day

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Fishing village in Martha's Vineyard, Cape Cod Massachusetts
Fishing village | Martha's Vineyard

Our Martha's Vineyard itinerary explores the island's beautiful beaches, hiking trails, and bike paths. With its weathered cape houses and salty seaside villages, Martha's Vineyard is a great place to experience authentic New England travel. Located off of the southern tip of Cape Cod, Massachusetts, visitors can fully discover each of the island's six villages in a week. Use our 'Martha's Vineyard Itinerary - 7 Day' to discover some 124 miles of beaches and 44 miles of paved bike paths.

Ocean Vistas on Cape Cod | Martha's Vineyard Itinerary 7 Day
Ocean Vistas on Martha's Vineyard


On the eastern end of the island there are three bustling up-island villages (Vineyard Haven, Oak Bluffs, and Edgartown). On the western side there are three rustic, down-island villages (Aquinnah, Chilmark, and W. Tisbury). Each has its own appeal. One commonality is a lack of chain stores and restaurants. Instead, expect endless coastline, gently rolling hills, dense woods, pastures, and endless things to do on Martha's Vineyard.

Gassing up in Menemsha | Martha's Vineyard Itinerary | Cape Cod Massachusetts
Gassing up in Menemsha


From mid-May to September, the island’s population swells from around 17,000 to 200,000. At this time of year, the island is hopping. Long, hot days bleed into breezy evenings. Everything is open. There are loads of concerts and shows to attend. Public transportation is at its peak.

Boardwalk to the Beach | Best Things to do in Martha's Vineyard | New England Travel Blog
Boardwalk to the Beach

Summer is fun, but the best time of year to visit Martha's Vineyard is in the autumn. The days from late-September to October are warm (65-75’), and the foliage does not peak until early November. The beaches, bike paths, and hiking trails are uncrowded. The locals relax. The pace slows. It’s paradise.

Menemsha, Martha's Vineyard | Things to do in Martha's Vineyard | Cape Cod, Massachusetts
Menemsha, Martha's Vineyard


Our Martha's Vineyard itinerary brings you up- and down- island to some of Randy and I's favorite places. If you are not a biker, you can hike portions of the trails mentioned. Working Joe Travel's list of the best things to do in Martha's Vineyard includes exploring Edgartown, biking in Oak Bluffs, beachcombing under the Cliff of Aquinnah, discovering lighthouses, and cruising the open sea. We hope you find the itinerary the right blend of relaxation and activity.

For more information on traveling to New England read our articles on:

Martha's Vineyard Itinerary 7 Day At A Glance
Sunset at the Beach | Martha's Vineyard Things To Do | New England Travel Blog
Sunset at the Beach


Most people arrive on Martha’s Vineyard by boat or airplane. Once on the island, there are rental cars, taxi-vans, private drivers, bikes, mopeds, and a bus system for transport. In the summer, it is not necessary to take a car to the island. The roads are crowded and there is little parking. It can be more relaxing to rent bikes and utilize the bus system.

Berries in the Field | Martha's Vineyard Day Trip | Cape Cod, Massachusetts
Berries in the Field

In the fall, the situation is different. The roads are uncrowded, there are plenty of places to park, and the buses do not run as frequently. As summer fades, the most efficient way to navigate the island is with a personal vehicle. Randy and I bring our car with a bike rack holding our bikes. We take the Steam Authority Ferry out of Woods Hole.

Estuary on Martha's Vineyard | Best Time to Visit Martha's Vineyard | New England Travel
Estuary on Martha's Vineyard


Each village on the island has its own charm. There are many types of lodgings throughout the island including luxury hotels, motels, inns, and private houses. In recent years, more establishments have been offering ‘suites’ which typically include small kitchenettes.

We recommend staying in Edgartown. The old whaling village is beautiful with its stately mansions, boutique shopping and lively wharf. It has wonderful restaurants, great nearby beaches, and the feeling of staying in a ‘real’ New England town. The village is centrally located and a great base for discovering all this Cape Cod, Massachusetts island has to offer.

Edgartown Lighthouse | Best Things to do in Martha's Vineyard, Cape Cod
Edgartown Lighthouse


Day 1: Woods Hole, Woods Hole Ferry, and Vineyard Haven

Make your reservation with the Steamship Authority for mid-day, but arrive early to tour Woods Hole. This interesting little village is home to a number of top scientific institutes. Many of these have hours open to the public. Try the exhibits at the New England Fisheries Science Center and the Woods Hole Oceanographic Institute.

Woods Hole Ferry to Vineyard Haven | Martha's Vineyard Itinerary | New England Travel
Woods Hole Ferry to Vineyard Haven

Between campus buildings, there are many artisan shops featuring unusual prints and weaves, photography, and crafts. Woods Hole also has some beautiful hiking. We suggest taking a walk through town and along the harbor. Then, trekking past the Coast Guard base and out to the Nobska Lighthouse (3 mile round trip).

Coast Guard Ship, Woods Hole | Martha's Vineyard Itinerary 7 Day | Cape Cod
Coast Guard Ship, Woods Hole

Have lunch on the deck of a local seafood restaurant before taking your place in line to board the Woods Hole ferry. The ferry ride is only 45 minutes, but plan on a few hours as it takes time to embark and disembark your vehicle.

Roofs of Vineyard Haven | Martha's Vineyard Things To Do | Cape Cod, Massachusetts
Roofs of Vineyard Haven

Once you arrive in Vineyard Haven, find a spot to park your car. Stroll around this lively, little beach town’s galleries and tees shirt shops. Sailboats and schooners fill the harbor. Walk the wharf and the piers. When you work up an appetite, go to the Black Dog Tavern for a waterfront meal. If there is a wait, poke around the company store. Its touristy and loads of fun.

Next, make your way to your lodgings and spend the rest of day exploring your surroundings.

Vineyard Haven & Black Dog Tavern | Martha's Vineyard, Cape Cod | New England
Vineyard Haven & Black Dog Tavern

Day 2: Biking to South Beach and Explore Edgartown

Start your day with a bike ride. The Edgartown to South Beach bike route is a 7-mile round trip on a paved bike path (Katama Road to Atlantic Dr. to Herring Creek Road). It starts in the center of Edgartown. Once you reach the edge of the village, the terrain is mostly easy spinning. At the entrance to South Beach, lock your bike in a rack and walk the wide-open beach known for its huge waves. There are no facilities so be sure to pack water and snacks.

Biking in Edgartown | Martha's Vineyard Itinerary | New England Travel
Biking in Edgartown
South Beach | Martha's Vineyard Itinerary | Cape Cod, Massachusetts
South Beach, Martha's Vineyard

Back at your room, take a break. Then, ready to explore Edgartown. The village is famous for so much; fabulous shopping, fine dining, a gorgeous working wharf, and stately white clapboard mansions. You can explore its historic homes and the Old Whaling Church. Or simply wander its quaint streets searching for unique clothing, jewelry and housewares.

Edgartown Harbor | Martha's Vineyard Day Trip | Cape Cod, Massachusetts
Edgartown Harbor

Day 3: Up Island Tour and the Cliffs of Aquinnah Road Trip

Drive to the Gay Head Lighthouse in Aquinnah at the southern tip of the island. Then, travel on to Wampanoag Reservation and the Aquinnah Cliffs. Once parked, you can trek along the trails at the top of cliffs for great views of the nearby Elizabeth Islands. Afterwards, walk along Moshup Beach for dramatic views of the multi-colored towering clay cliffs.

Gay Head Lighthouse | Martha's Vineyard Attractions | New England Travel
Gay Head Lighthouse
The Cliffs of Aquinnah | Martha's Vineyard Day Trip, Cape Cod
The Cliffs of Aquinnah

Our next stop is the village of Menemsha. The historic fishing village has been worked by the same families for generations. Stop for lunch in this colorful, low-key, quintessentially New England port. There are fish markets and cook to order restaurants onsite. After eating, stroll along the beach.

Fishing Village | Menemsha | Martha's Vineyard Itinerary 7 Day
Fishing Village | Menemsha
Fisherman on Martha's Vineyard | Martha's Vineyard Day Trip | Cape Cod
Fisherman on Martha's Vineyard

Loop through the towns of Chilmark and West Tisbury, or motor along a north-west route. The interior of the island is wooded. There are lots of farms and artisan’s galleries. Keep an eye out for open studios, sculpture galleries, and antique shops.

Sea Sculpture Menemsha | Things to do in Martha's Vineyard | New England Travel
Sea Sculpture Menemsha

Day 4: Oak Bluffs Biking

Beginning in Edgartown, take the 6 mile bike trail to Oak Bluffs via Beach Road. This flat, paved trail will take you past fantastic views of Nantucket Sound on one side of the trail, and Sengekontacket Pond on the other.

Sea Grass Along the Trail | Martha's Vineyard Cape Cod
Sea Grass Along the Trail

When you reach Oak Bluffs, rest for awhile in Ocean Park, a 7-acre green space that overlooks the ocean. When you are ready to start pedaling again, cruise through the charming streets of the Camp Meeting Association with its rows of colorful gingerbread cottages. There is a lovely harbor to explore, a vibrant main street (Circuit Ave.) to shop, and a carousel from the 1800s, the Flying Horse, to ride.

Oak Bluff Ginger Bread Cottages | Things to do in Martha's Village | Cape Cod, Massachusetts
Oak Bluff Ginger Bread Cottages
The Harbor at Oak Bluffs | Martha's Vineyard Itinerary | New England Travel Blog
The Harbor at Oak Bluffs

When you are ready to return to Edgartown you can take a paved in-island route, or as Joe and I prefer, take the same route back. This time pause along the route, to walk along the 5-mile long State Beach. Pause at the Oak Bluffs / Edgartown town line and jump off of “Jaws” bridge (made famous in the movie by the same name) – or just watch the young people take the plunge.

The "Jaws" Bridge, Martha's Vineyard | Cape Cod Massachusetts
The "Jaws" Bridge, Martha's Vineyard

Day 5: Day at Sea / Water Sports and Down Time

To truly experience the island, you must also see it from the sea. There are so many ways to get out on the water. There are sea kayaking, catamaran, schooner, sail boat, jet ski, and party boat tours and rentals. We have enjoyed a number of these experiences over the years. Perhaps our favorite, was a day spent blue fishing on a privately chartered fishing boat. There were 6-8 of us on board. After a bit of scouting, the blues started biting and we spent the rest of the afternoon wrestling these spectacular fish out of the ocean. That night, with bruised backs and upper arms, we feasted.

Fishing Boats | Martha's Vineyard Things to Do | New England
Fishing Boats on Martha's Vineyard

Day 6: Morning hiking (or biking) and a Lighthouse Tour

This morning get outside. If you feel like a bike ride, try one of the State Forest Loops. There is a 3-mile and a 10-mile paved route about 4 miles outside of Edgartown. Or, if you feel like a hike, drive to the Long Point Wild Life Refuge in West Tisbury. The refuge has miles of trails with ocean vistas. There are single track trails, dirt roads, boardwalks and beaches to trek over. Bring binoculars!

Hiking on Martha's Vineyard | Things to do in Martha's Vineyard | Cape Cod
Hiking on Martha's Vineyard

Depending on where you spent the morning, map out a route that will take you to the island’s lighthouses (all located by beautiful vistas and nearby beaches). Include the East and West Chop Lighthouses, and Edgartown Light.

West Chop Lighthouse, Vineyard Haven | Martha's Vineyard Itinerary | Cape Cod
West Chop Lighthouse

Day 7: Chill Day

Shopping. Beach. Pool. Pack.

Let's do this again next year, Laura and Randy

For more information on traveling to New England read our articles on:

Chilling on Martha's Vineyard | Cape Cod, Massachusetts
Chilling on Martha's Vineyard


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