Towns of Martha’s Vineyard

Jen O'Hanlon, REALTOR®


Martha's Vineyard is an island in Massachusetts seven miles off the coast of Cape Cod. The Island is approximately 96 square miles, a bit triangular in shape and 25 miles east to west, and about nine miles north to south. Amazingly, the population goes from about 17,000 in the off-season to 200,000 in the summer. Although the population has grown significantly over the years, the Island prides itself on its land management and success in creating permanent open spaces for everyone to enjoy.
You won't see a fast-food restaurant or a big box store on the Island as preserving the local character has always been a top priority of town governments and residents alike. You also won't find any traffic lights; the maximum speed is 45 miles an hour. There are six towns, and they all have their unique attributes and character.

Jen O'Hanlon, founder of the O'Hanlon Group

Edgartown was established in 1642 and known for its whaling history. The town is charming, to say the least, and can make you feel like you've stepped back in time with the narrow streets and historic buildings. There are many wonderful shops and restaurants in Edgartown Village and plenty of ice cream stores to choose from. The 4th of July is celebrated in style with a small-town parade and fireworks display over the harbor. Edgartown harbor is full of visitors who rent moorings and stay on their boats during the summer. Many people are drawn to the history and charm of the whaling captain's homes, and most of these in-town homes have been updated over the years, preserving the charm of an old home with all of the modern conveniences so many are accustomed to. 

Edgartown Lighthouse

The Harbor View Hotel, which first opened in 1891, is one of the best spots to enjoy lighthouse views while watching boats come and go. Chappaquiddick, fondly known as Chappy, is an island off of Edgartown, and it is known for its pristine shoreline and fantastic fishing; you can even drive your SUV onto the beach and find that perfect private spot. Getting to Chappy is by the three-car ferry that operates year-round. Chappy Island has no restaurants, stores, or gas stations. It offers lovely seclusion while just a few minutes ferry ride away from Edgartown. Katama is an area of Edgartown to the south of the town. It is loved by many for its proximity to South Beach and the great bike paths that go all the way from downtown Edgartown to the beach. While there are many homes in Katama, there's also a small airfield, two restaurants, and 160 acres of farmland restricted to agricultural and conservation use. 

Oak Bluffs is another "Down Island" town and when you come off the ferry here, you can't miss Ocean Park. It is the perfect spot to fly a kite or have a picnic between the town's main street and the ocean. This colorful town is extremely popular with day-trippers due to the passenger ferries coming and going from Falmouth, New Bedford, and Hyannis. The beautiful Victorian homes around the park enjoy ocean views and the perfect in-town location. The Martha's Vineyard Campground is our favorite part of Oak Bluffs. The unique history dates back to 1835, when methodist summer retreats were first held here, and tents were put up to house the group. Over the years, the cottages were built inspired by those tents. The colorful and ornate gingerbread cottages always bring a smile to our faces when we stroll through the campground. On the third Wednesday in August every year, Grand Illumination is held; paper lanterns are hung from the porches and are all turned on at the same time. Needless to say, this is a must-see event if you're on the island that week.

Ocean Park Gazebo In Oak Bluffs

During the summer, Oak Bluffs is bustling with tourists and locals enjoying the beaches, shopping, and restaurants. The main street, Circuit Avenue, is always lively, with people visiting shops and ice cream parlors and enjoying the nightlife. If fishing or boating is your thing, you'll want to know about the Oak Bluffs Marina. It is the largest on the Island, and the dockside activity is always lively, to say the least. The Oak Bluffs beaches are not to be missed. Inkwell beach is a popular spot to catch some rays close to town. If you want a long stroll on the beach, head to state beach just east of town and enjoy two miles of shoreline. This beach is popular because of its shallow waters and small waves. It's also an excellent spot for shellfishing. One of the historic landmarks in Oak Bluffs is the Flying Horses Carousel, constructed in 1876. The Flying Horses is the nation's oldest platform carousel located near the marina in the heart of the town. Summer on the Vineyard wouldn't be complete without fireworks, and Oak Bluffs does that in style every august. 

Less than 4 miles away is a town called Vineyard Haven. Before the Cape Cod Canal was opened in 1914, Vineyard Haven harbor was a common stop for ships traveling to and from Boston and New York. For over 200 years, Vineyard haven's history as a shipbuilding port began during that time when ships often had to stop for repairs and maintenance. Tisbury often referred to as Vineyard Haven by the locals, is our year-round town. The car ferry enters Vineyard Haven year-round, and most shops and cafes are open in the off-season. Before the world-famous black dog t-shirts were created, there was the Black Dog Tavern; opened by captain Robert S Douglas who first arrived in Vineyard Haven in 1964 with his schooner, the Shenandoah. The tavern continues to be a favorite spot for islanders and visitors alike. 

Steamship Authority Dock

The Martha's Vineyard Museum is located in Vineyard Haven and originally opened in Edgartown in 1922. A long-overdue expansion was necessary, and in June of 2019, the new museum opened its doors at the carefully restored and enhanced 1895 marine hospital.

West Tisbury is home to the farmers' market, an island tradition since 1974. Every Wednesday and Saturday from June through October, the Martha's Vineyard Agricultural Hall is home to the West Tisbury farmers market. This glorious open, fair market features local baked goods, fresh flowers, produce, seafood, meat cheeses, and many other island-grown products. Also, the MV Agricultural Society livestock show and fair are at the AG Hall every summer. This four-day event in August has been an Island institution since 1858 and was only canceled twice for four years during world war II and then in 2020 during the Covid 19 pandemic. 

Lambert's Cove beach is also in West Tisbury and is one of the most coveted beaches on the whole Island. On Vineyard sound, you'll find calm waters and a large sandy beach; it is never too crowded because it is only for residents of West Tisbury, and parking is limited. 

Chappy Ferry

There are miles of paved and unpaved trails through the Manuel F. Correllus state forest, located both in West Tisbury and Edgartown, and provide endless options for joggers, bikers, and horseback riders. West Tisbury is known as one of the three up-island towns which enjoy a more rural setting than Edgartown, Vineyard Haven, and Oak Bluffs. The term up Island originates from the sea-farers who referred to longitude line numbers going up as you head west. 

Further west is Chilmark, one of the most charming fishing villages on the east coast. Even the locals come to Menemsha to take in the sunsets and enjoy this quintessential fishing village of Chilmark. With its bustling dock and little fishing shacks, the beach located next to the harbor jetty is the best place on the Island to enjoy the magic of a Martha's Vineyard sunset. The trip isn't complete without some soft-serve ice cream at the Galley. 
Many would say that Lucy Vincent is the most beautiful beach on Martha's Vineyard; it is located on the south shore and has a magnificent cliffside and a wide sandy beach open to town residents and guests only. You'll want to come and visit in the off-season if you're not staying in Chilmark. When not at the beach, country life is what Chilmark is all about; the old stone walls and rolling fields take you back in time. There are many great walking trails in Chilmark, including Wisconsin's rock, Menemsha Hills, and the Brickyard, but blink, and you'll miss the town center. There's just a tiny post office, a general store, and one restaurant. After you've made your way through Chilmark, you'll enter Aquinnah, home of the red clay cliffs and the famous Gay Head lighthouse.

While the whole island is full of exciting history, Aquinnah may take the prize. The Wampanoag Tribe of Gayhead owns nearly 500 acres of the land in the area and has been on the Island for more than 10 000 years. The tribe's cultural district is right by the lighthouse and features several stores, the Aquinnah's shop, a restaurant overlooking the ocean, and the famous clay cliffs. Moshup Beach is a public beach at the foot of the cliffs and is one of the most stunning spots on the Island. It's definitely worth a visit, but don't plan to take any clay with you as it's against the law. 

Gay Head Lighthouse in Aquinnah

In 1799 the Gay Head lighthouse became the first lighthouse on Martha's Vineyard. It was needed to help ensure safe passage for shipping traffic through the Vineyard sound between the cliffs and the Elizabeth Islands. Over time the red brick lighthouse has been updated and preserved, and in 2015, it was moved 134 feet to a safer location

From the plane fields of Katama to the rolling hills of Chilmark and the cliffs of Gay Head, the Island's geography changes significantly from one end to the other. There are so many different things to do within each town's offerings.

It's truly impossible not to enjoy the Island no matter what time of year you come. We cannot wait to welcome you to our little paradise. 
Watch Jen O'Hanlon tour the island and make sure to subscribe for all things Martha's Vineyard on YouTube



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