By Flickr user David Berkowitz
Martha’s Vineyard promises the quintessential New England vacation experience: long stretches of sand; a green, pastoral interior; lighthouses; elegant marinas; gorgeous homes and hotels; and authentically local cafes, bars and restaurants. The fishing is good, the food is excellent, the scenery is perfect, you can catch the ferry to Cape Cod, and yes, Jaws was filmed here!
Martha’s Vineyard gets very busy in the summer months, so it’s worth considering where to stay in advance. Luxurious Edgartown is a classic choice and a good option for first-time visitors, because it’s so quintessentially New England: expect the homes of old seafarers, upmarket restaurants and cafes, elegant boutique shopping, charming, walkable streets, and easy ferry access to the beaches and islands. Oak Bluffs is a good neighbourhood for beach lovers and families, but it also has some lively nightlife options. West Tisbury is a green and peaceful pick, ideal for anyone hoping for a really relaxed break. “Up island”, Chilmark and Aquinnah have a larger population of year-round residents (fishermen and farmers), as well as arty types, and essential workers.
Ideal for: beach break, family holiday, relaxed vacation, romantic escape
Edgartown is a classic New England vacation destination. It’s located on the eastern side of Martha’s Vineyard and was the first bit of the area to be settled, around 1640. The atmosphere, architecture, beaches and landscape of Edgartown are all appealing. There are a number of historic homes, many built by sea captains, and plenty of charming picket fences along streets neatly lined with 19th century architecture. There are also whaling and sailing churches, and two of Martha’s Vineyard’s five lighthouses. Edgartown also has a charming, protected harbour, with ample mooring. Its nine beaches are open to the public, but just two and a half miles outside of town is South Beach, which has fantastic facilities for sailing and water sports. Edgartown’s reputation for great restaurants is well known, and its reputation for boutique and gallery shopping is also solid.
Did you know? Edgartown has had a few names during its time, including Nunnepog, but it's never been called Edgarton.
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Ideal for: beach breaks, family holidays, fishing and sailing, relaxed vacation
Image by KathyBarclay from Pixabay
Oak Bluff is renowned for its colourful “gingerbread houses”: Victorian-built and wonderfully whimsical, these houses were built in the latter half of the 19th century as the Martha’s Vineyard Camp Meeting Association (a Christian holiday camp that you’re still able to book the cottages through today). Other reasons to choose to stay in Oak Bluffs include the beautiful, bustling harbour, which offers opportunities for watersports and chartering boats for fishing or sailing. It also has the largest marina on the island. The beaches are lovely — notably Inkwell and State Beaches — and Oak Bluffs has a fantastic reputation for food and drink, especially ice cream. The Main Street is lined with charming boutiques and art galleries.
Did you know? Oak Bluffs has the oldest operating carousel in the US, with a charming collection of steeds still up for fun even after around 150 years.
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Ideal for: beach breaks, family holiday, sightseeing, sailing and fishing, relaxing escapes
The Vineyard Haven village is in the town of Tisbury: it’s the bit around the historic harbour and shipyards, from the ocean, along Beach Road and Main Street to the library. The stretch has historic sights and the harbour, but also a commercial zone with boutiques, galleries and studios, and plenty of restaurants, cafes and bars. There are plenty of old whaling captains’ and merchants’ houses as you walk further into Tisbury proper, along with a historic cemetery, the Martha’s Vineyard Film Centre, the Martha’s Vineyard Playhouse, and the Martha’s Vineyard Museum, which was converted from a former Marine Hospital. Vineyard Haven has a row of beaches, including Owen Park beach, which is lovely for families. The West Chop lighthouse is also worth visiting.
Did you know? Vineyard Haven is only the name of one section of the town of Tisbury, but the names are used interchangeably, and Vineyard Haven is commonly used as a title for the whole town
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Ideal for: relaxed escapes, family holidays, rural retreats
By Flickr user Ernest McGray, Jr.
West Tisbury is an up-island town, one of the less touristy towns of Martha’s Vineyard, in the island’s agricultural heartland. The other ‘up-island’ towns are Chilmark and Aquinnah. There are still second homes here, and some lovely accommodation options, including guesthouses and B&Bs, but this is also a settlement of farmers and fishermen, and you’ll definitely see historic farmhouses. West Tisbury is also known for its forests and ponds, the West Tisbury Farmer’s Market, the Polly Hill Arboretum, and its historic general store, called Alley’s. West Tisbury also has a number of galleries and artists’ studios, and it’s close to Martha’s Vineyard Airport.
Did you know? Alley's is the oldest shop on the island, famous for selling penny candy.
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Ideal for: relaxed escapes, family holidays, beach breaks, foodies
Chilmark is an ‘up-island’ town with some beautiful beaches and a rolling, green interior interwoven with charming, old low stone walls. These days it’s also known as a favourite vacation spot for the Obama family, who rent out an estate called Blue Heron Farm. As well as the peace they come for Menemsha, an historic, but working fishing village, and Menemsha Beach, a beautiful local beach, with smashing sunsets and fantastic seafood you can buy fresh from the docks. Much of the area surrounding Chilmark is protected, and there are some spectacular walking and hiking trails. In March, Chilmark hosts a film festival, and in the summer, they host some great markets.
Did you know? The sunsets at Menemsha Beach are so beautiful that crowds often gather and applaud the sun as it dips below the water
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Ideal for: relaxed escapes, beach breaks, families, walkers, fossil hunters, sightseeing
Image by Susan OLeary from Pixabay
Aquinnah is the third ‘up island’ town, located in a remote, clifftop spot on the western tip of Martha’s Vineyard. The town used to be called Gay Head, named for the fantastically colourful clay cliffs it sits atop. The cliffs, and the view from them, are very special: the cliffs have stripes of bright rust, pale lemons and peaches, and blacks too, and from the top of them you can see the Vineyard Sound, all the way to the Elizabeth Islands. The cliffs are fragile, though, eroding at a rate that must be quite alarming for residents, but which does mean that fossils are forever being brought close to the surface of the cliffs, so it’s a great destination for fossil hunting. It’s also brilliant for birdwatching. Aquinnah’s beaches are probably the main reason to stay here, though. Not all of them are public, but there is still a good choice amongst those that are. The Wampanoag indigenous tribe have lived in this area for thousands of years, and still do today, and they bring their rich cultural history to the town in many forms, including to the local shops and businesses. If you want landmarks, visit the lighthouse and the Aquinnah Cultural Centre.
Did you know? In 2015, the historic Gay Head Lighthouse was moved 39 metres inland to help it escape the speed at which the cliffs are eroding.