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A ridiculously cute guide to Oak Bluffs & Martha's Vineyard

Endless old-school summer vibes.

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Created by Roadtrippers - January 30th 2017

The island of Martha's Vineyard has had a reputation for being a vacation getaway spot for the East Coast's rich and glamorous for decades. Everyone from Hillary Clinton to Bill Murray has soaked in the fresh ocean air, lovely scenery, and nostalgic summer vacation vibes of The Vineyard-- and with good reason. But, you don't need to be Old Money rich to visit; heck, you don't even need to be New Money rich! A refreshing 35-minute ferry ride will take you to and from Martha's Vineyard for a quick day trip from Boston, or you can snag a spot in one of the many quaint inns or B&Bs that dot the island. However you spend the rest of your vacation is up to you... but whatever you plan to do, you're sure to fall madly in love with the breezy, vacation-ready atmosphere!

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Set the scene for your adventures across the island with a stroll past the town of Oak Bluff's signature Gingerbread Cottages. The history of how these fairytale Victorians came to exist is the story of Martha's Vineyard itself. It all started in the mid-19th century when the island was primarily used as a spot to host multi-day religious revivalist meetings. Families who came back summer after summer would set up tents, which gave way to slightly nicer tents, which eventually morphed into cottages, which steadily became more and more elaborate and colorful as the families tried to one-up each other. Scrollwork, porches, framing, bright colors, and other details add a storybook effect to the charming homes of Oak Bluff. It's unlike any other neighborhood in the country, and it's sure to inspire your next home decor project.

Polly Hill Arboretum

Step back even further in time at the island's Polly Hill Arboretum. With the main office housed in a 1670-era home, and historic farmhouse buildings scattered across the property, this is one of the best examples of how bucolic life has been on Martha's Vineyard. Throughout the grounds, you'll see plenty of plant life, too. Look for azaleas, witch-hazels, camellias, magnolias, rhododendrons, and tons more. The whole place is just begging to host a cozy little picnic lunch, if you ask me!

Menemsha Beach

Offering sweeping views of the Vineyard Sound, Menemsha Beach is a quiet beach with gentle waves and stunning sunsets. It's a popular harbor for fishing boats to bring in their catch. It's a public beach (many beaches on the island are private, or don't offer parking like Menemsha) so it should be pretty easy to reach via car or bus. The town of Menemsha has some great little shops and restaurants, and if you explore the dunes along the shore, you'll stumble upon a unique statue of a swordfish harpooner. This side of the island is a little quieter, so it's a nice spot to relax.


Chilmark, MA

You can't say that you took a trip to New England without visiting at least one historic lighthouse! Martha's Vineyard alone has five, making the island the spot with the highest concentration of lighthouses in the country. There's been a lighthouse here at Gay Head for ages, with the first one built in 1799. The light guides ships across an especially rough patch of water known as the Devil's Bridge. There's an incredibly well-documented history behind the lighthouse, and it's open seasonally, with guided tours. Pro tip: On Thursdays in July and August, it's open a little later for sunset tours!


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Summercamp Hotel

There are loads of New England-style inns in old seaside mansions on the island, but for a different change of pace, the Summercamp Hotel in Oak Bluffs is super fun. It melds the vintage atmosphere with fun, modern pops of color and touches. They've got a porch with swings and rocking chairs, and a super nice pool, along with cozy rooms and a funky lobby. Another bonus of staying here? They have a killer location within walking distance of the harbor (and the ferry!).

Flying Horses Carousel

Another famously whimsical attraction on Martha's Vineyard? The Flying Horses Carousel. It's the country's oldest platform carousel, having been built back in 1876. It was originally an amusement at New York's Coney Island, but it was moved into a red barn on the island in 1884. The carousel has been kept in impeccable shape and is open for rides (kids and adults alike are welcome) during the summer season. They're one of the only carousels that still offers free rides for anyone who can grab a brass ring, so take a go at it and enjoy the classic experience!

Offshore Ale Brewing Company

Whether you just want to unwind with a craft brew and some free peanuts, or you're looking for a casual spot to grab some New England grub, Offshore Ale Brewing Company is a gem. They make some great, easy-drinking beers like the Hop Goddess Ale, the Steeprock Stout and the lightly fruity Offshore Blueberry. As for their food, you'll find clam chowder, steamed mussels, fried calamari, oysters on the half shell, fisherman's stew, fish and chips, and more for those looking to indulge in fresh seafood. If you're craving something else, they have amazing chicken wings, a great burger, and all kinds of pizza as well.

Behind the Bookstore

Edgartown is another village worth visiting on the island. Make a point to stop by Edgartown Books to browse their offerings for something to read on the beach, or on the porch of your hotel. After you're done in the bookstore, go around the back to Behind the Bookstore, the cutest little cafe on the island. From cold brew and pour-overs to cortados, matcha, and Turkish coffee, they've got everything a coffee-lover could want. They also have breakfast (think, shakshuka, hand-cured salmon on housemade rye, and lemon-poppyseed griddlecakes) and light lunch plates (salads, sandwiches, and toast), along with cocktails and bar bites. You could easily spend all day here, reading, snacking, sipping, and enjoying the hidden gem.

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Once you step onto the island, you'll pretty much step into a storybook. Flying horses, gingerbread cottages, sunset lighthouse tours, picnics beneath magnolia trees, secret garden coffee shops, ocean views from the hotel porch swing... can it honestly get any more perfect than this?


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