Meet Our Neighbor: 6 Fun Things to Do in Oak Bluffs

We feel sorry for folks who don’t get along with their neighbors — because we love ours! Oak Bluffs is a leisurely seven miles from Edgartown and easy to get to by car, bus, or bike. On your visit, carve out some time for swimming, sightseeing, and sweets with a few of our favorite things to do in Oak Bluffs.


See the Sights on a Bike

Photo: Amy Meredith via flickr (CC BY-ND 2.0)

No car? No problem! Save your visit for a day with clear skies and get there by bike in about half an hour. Follow Beach Road from Edgartown to Oak Bluffs for a scenic route along the waterfront and Caroline Tuthill Wildlife Preserve. Keep an eye out for the Jaws Bridge along your journey! Keep pedaling until you take a left onto Tuckernuck Ave where you’ll spill out into Circuit Avenue — the hub of fun things to do in Oak Bluffs.


Go for a Seasonal Swim

Martha’s Vineyard beaches are the bread and butter of every island vacation, and Oak Bluffs is home to one of our favorites. Joseph Sylvia State Beach (simply “State Beach” if you want to be in-the-know) boasts two miles of sandy bliss. The shallow waters and generally gentle waves make this one of the best options for swimmers and families with floaties in-tow.


Be a Tourist

First-time visitors have a few must-see sights to add to their list of things to do in Oak Bluffs. Keep your camera or phone at the ready as you stroll through the Martha’s Vineyard Campmeeting Association. You’ll recognize the iconic collection of brightly colored, intricately designed Gingerbread Houses and The Tabernacle. When your feet need a break, take a spin on the Flying Horses Carousel (America’s oldest!) to see how many brass rings you can collect.


Delight in Downtown Shopping

Photo: 6SN7 via flickr (CC BY 2.0)

Circuit Avenue in Oak Bluffs is a shopper’s paradise, so carve out plenty of time to pop into all of the shops here. You’ll find familiar island names like Vineyard Vines and The Black Dog alongside local gems like The Lazy Frog game store or the eclectic Craftworks craft store. Hopefully, you’ve saved room in your suitcase for souvenirs because you’ll find a dozen island gift shops along the avenue. There’s space for one more coffee mug in the cabinet, right?


Pick Up a Pick-Me-Up

More interested in treating yourself to something tasty than something tactile? Oak Bluffs has a number of ways to indulge the sweet and savory visitor. Pick up a pint of Vineyard-brewed beer at Offshore Ale Company, and share a pie from their wood-fired pizza menu. On a hot summer day, you’ll have your pick of ice cream shops to grab a scoop like Mad Martha’s, Ben and Bill’s, or the new Rosie’s Frozen Yogurt (an island first!). For treats baked to perfection, drop by Martha’s Vineyard Gourmet Cafe’ & Bakery for cupcakes, donuts, and apple fritters (a local favorite).  


Visit East Chop Lighthouse

If you’re conducting your own Martha’s Vineyard lighthouse tour, you can check one of the five off the list here. One of the top things to do in Oak Bluffs is pay a visit to the historic East Chop Lighthouse. While the structure itself is commanding on its own, the beautiful backdrop of Vineyard Haven Harbor makes this bluff even more picture-perfect. If you play your cards right, you can witness a photo-worthy sunset alongside a peek inside the lighthouse.

Photo: Massachusetts Office of Travel & Tourism via flickr (CC BY-ND 2.0)


Once your day trip has concluded, bring your souvenirs (real or story-form) back to the Square. Relive the best parts of the day’s adventures over a drink at Chesca’s or catch up on some much needed R&R tucked away in the comfort of your room.

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