Martha’s Vineyard’s Cottage Town: Oak Bluffs Travel Guide // Brittany from Boston

Martha’s Vineyard’s Cottage Town: Oak Bluffs Travel Guide

Posted on Posted in Boston, North America, Travel

Martha’s Vineyard is not only the locals’ favorite summer colony, it also draws visitors from the country and world over who have heard of its quaint, traditional charm. All around the island, you’ll find Cape-style homes with bare wood-paneled exteriors weathered by the warm summer sun, and hydrangea bushes taking over their front yards. You’ll see boats in the harbors that are well-loved and actively-used, you’ll see families on the beaches with children building sandcastles as high as they possibly can, an old island-native walking his black Labrador down the block, and American flags fluttering in the wind on every lawn. Life is slow here, so slow that it’s almost stuck in time. If it is stuck in time, it’s a time when the neighbors were actually friends, when their biggest worry was whether it was a good beach day, and when the simple joys of the sea and the sun dictated the pace of things. Martha’s Vineyard is a time-honored favorite, and as soon as you see it for yourself you’ll understand why. When the mainland-ers are making their annual summer trek out to Martha’s Vineyard, they have a few options of where to stay on this little island. Edgartown is great for shopping, Vineyard Haven is the place to go for the most action this little island can muster, and Aquinnah is where you go to get away from it all. But Oak Bluffs is where the charm and character lives on in its purest form. Oak Bluffs is Martha’s Vineyard’s Worst-Kept Secret and the one place you need to know when planning your vacation. Here’s what you need to know for your visit, your Oak Bluffs Travel Guide.

Martha’s Vineyard’s Cottage Town: Oak Bluffs Travel Guide // Brittany from Boston

Oak Bluffs Travel Guide

When To Go

Summer is when the island is the most amiable and lively, when the beaches fill up with visitors and the island swells in population. The summer is the high season, from June to August. Because it is such a popular time to visit, it is quite crowded and actually you can find it difficult to secure accommodation. If you want to visit in the summer, which is the best time, then you should think about booking your accommodation a year ahead of time. It’s not possible to book a last-minute trip for Martha’s Vineyard in the summer. However you can also try to visit in the shoulder season, in May or September, when you will still enjoy some nice weather. But I would advise against visiting in winter, as there is very little to do, many businesses are closed for the season, and the charm of the island is masked by the challenging weather.

How To Get There

By far the most popular way to reach Martha’s Vineyard is by ferry and there are several companies that operate ferry service between the mainland and the island. In fact, several ferries actually arrive directly in Oak Bluffs. Steamship Authority departs from Woods Hole, Hy-Line Cruises departs from Hyannis and Nantucket, Island Queen departs from Falmouth, and Seastreak departs from New Bedford, New York, and New Jersey. In order to reach the ferry launch points you can park at one of the affiliated parking lots and board the shuttle bus to the harbor. If you are traveling from Boston you can take the CapeFlyer train to Cape Cod and then take the shuttle to the ferry, though these trains operate on a limited basis. Other than traveling by ferry, you can also have the option to travel to Martha’s Vineyard by plane, helicopter, or personal boat charter.

Martha’s Vineyard’s Cottage Town: Oak Bluffs Travel Guide // Brittany from Boston

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What To Do

Oak Bluffs is home to the famous gingerbread cottages, which transport visitors back in time to the 1800s when they were constructed. This collection of homes, totaling over 300 cottages, have a whimsical fairy-like architectural style complemented by bright paint colors. These homes have often been with a family for many generations, some dating back to the origin of the homes, when they were tent camping plots, before they were built into wooden cottages. It’s a lovely neighborhood to walk through, admiring and photographing the various homes, and chatting with the owners who can often be found relaxing in rocking chairs on their front porch.

In keeping with the expectations of an island getaway, you can enjoy a day at the beach, a walk up to one of the lighthouses, or a stroll around the marina to admire the boats, when you’re here in Oak Bluffs. Inkwell Beach is quite nearby to town but if you want a quieter beach experience, head out to Joseph Sylvia State Beach. The East Chop Lighthouse is a pleasant 45-minute walk from downtown. When you’re passing through the downtown area, you’ll want to stop in to do some local shopping and I recommend you visit Slip 77, Secret Garden, and Island Images Gallery. You may also enjoy taking a bike or scooter rental to explore around town or the rest of the island, and there are plenty of shops offering these rentals in town. You can take a sunset boat tour from the Oak Bluffs marina to get a different view of the island, available with Plan Sea Adventure Charters or The Skipper. And of course you can take some daytrips to explore the rest of the island, and you can use the island bus service to travel around between towns.

Martha’s Vineyard’s Cottage Town: Oak Bluffs Travel Guide // Brittany from Boston

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Where To Eat

There is an abundance of fresh and delicious seafood in Oak Bluffs. Nancy’s and Sand Bar & Grille enjoy great views overlooking the marina, especially during sunset. The selection of whiskeys at 20byNine is the perfect complement to a cozy delicious dinner one night while you’re in town. Lola’s  is the locals’ favorite dinner spot. And Slice of Life offers delicious healthy options, so good that President Obama ate there! Don’t forget to finish each day with an ice cream, because you are on vacation after all. My favorite ice cream shops are Mad Martha’s and Vineyard’s Best Ice Cream.

Then of course at night there is some nightlife on the island, for those who are not already exhausted from playing in the sun all day. Sundowner drinks with a view of the sunset are available all along the marina. Try Offshore Ale Co. and Lookout Tavern.

Martha’s Vineyard’s Cottage Town: Oak Bluffs Travel Guide // Brittany from Boston

Where To Stay

Oak Bluffs and in fact all of Martha’s Vineyard is characterized by its quaint small-town style, so you won’t be surprised that they have no big hotels here. There are some boutique hotels and B&B’s available on the island, which are really beautifully designed and offer you a unique feel for Martha’s Vineyard. Some of my favorites are The Oak Bluffs Inn, Summercamp Hotel, & Pequot Hotel. It’s also very nice to visit with a group of friends or your family, and in fact this is the way that most people visit the island. The typical way to stay at Martha’s Vineyard is by renting a home for a week, which is handled by such property management firms as Martha’s Vineyard Island Home Realty and Anchor Realty. Sometimes you will find these homes listed on home-sharing websites like airbnb, but it’s a time-honored tradition to take a week-long rental of a home on Martha’s Vineyard from the local rental companies. This is a nice tradition actually because you have the opportunity to settle in to island life and fit into the neighborhood and community. You have your own home for the week, with a porch to sit out for a coffee in the morning or a sundowner at night, with a grill to make your own BBQ, with a living room where you’ll gather and create memories from the trip, and with your own space to enjoy restful nights after lots of time in the sun all day. If you can manage to get a bit of a group together and rent a home on Martha’s Vineyard, it’s really the best way to experience the island. These rentals are often booked far ahead of time, and in fact it’s not too soon to book next year’s trip this summer, though the winter or spring beforehand will usually still have plenty to choose from. With the gingerbread cottages, the situation is even more unique because they are historic properties and the local governance restricts their rental period to just 6 weeks each summer so these will need to be booked a full year in advance.

Martha’s Vineyard’s Cottage Town: Oak Bluffs Travel Guide // Brittany from Boston

Martha’s Vineyard’s Cottage Town: Oak Bluffs Travel Guide // Brittany from Boston

Martha’s Vineyard’s Cottage Town: Oak Bluffs Travel Guide // Brittany from Boston


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