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One Day in Oak Bluffs, Martha’s Vineyard

One Day in Oak Bluffs, Martha’s Vineyard

A few weekends ago, my family and I took a day trip to Martha’s Vineyard. My parents, sister, and aunt left early in the morning to hit all the major towns in MV, but as I don’t enjoy waking up early, my boyfriend and I grabbed the ferry at around noon.

I haven’t been to the Vineyard since I was a little kid, so I hardly remember it at all. From what I’ve heard, Oak Bluffs is the “hub” of the Vineyard; once I got there, I immediately knew why. The shops and spots are quintessentially New England when it comes to the architecture, vibe, cuisine, and fashion. Since I enjoyed my day in Oak Bluffs, MV, I’ve shared a breakdown of the highlights, in case you decide to make a stop in this quaint town.


Getting There

Since Martha’s Vineyard is an island, you’ll need to catch a ferry. There are multiple ferries from Falmouth, Hyannis, and New Bedford that will take you to the Vineyard. If you’re coming from a farther distance, you can even catch a ferry from Rhode Island, New York, or New Jersey. Make sure you keep an eye on your respective ferry schedule; if you miss the last one, you’ll probably have to book a hotel and stay the night!

Take me back please 😞#homesick #boston

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What to Do

Walk along the “gingerbread” cottages

This gorgeous sight was probably the highlight of my recent day trip to Oak Bluffs. These nineteenth-century cottages may be the most quaint, picturesque homes I’ve seen since my trip to Amsterdam in 2014. With the ornate trim and bright colors, these homes look like something out of a fairytale.

oak bluffs martha's vineyard


Get a tan on Joseph Sylvia State Beach

If you’re looking for a change of scenery from downtown Oak Bluffs, catch a bus over to State Beach. You can lounge in the sun or rent a paddleboat or kayak to work off the calories you’ll be eating later in fried seafood and beer. If you’re feeling brave, take a plunge off the “Jaws Bridge,” the famous filming location from the hit blockbuster.

This day will be one to remember! 💯✔ #JawsBridge #GoodTimes #Summer2017

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Ride the Flying Horses Carousel

Known as the oldest platform carousel in the U.S., this historical site was built in 1876 in Coney Island and transported to Oak Bluffs in 1884. You can watch eager children grab the rings, in search of the lucky brass ring, or you can take on the challenge yourself (as I did). If you grab the brass ring, you get to stay onboard for a free ride.

oak bluffs martha's vineyard


Go shopping on Circuit Avenue.

This tourist-packed street consists of some of the best ice cream shops, bakeries, and shops in Oak Bluffs’ downtown area. Grab a “Martha’s Vineyard” sweatshirt, Jaws T-shirt, or other item that nonverbally brags about your trip to Cape Cod. Circuit Avenue makes for some great people-watching, as I’m sure you can imagine.

oak bluffs martha's vineyard


Stroll through Ocean Park

If you want some fresh air but don’t feel like getting all sandy at the beach, make your way over to Ocean Park, which is practically steps away from the ferry. Whether you’re bringing a picnic lunch, a frisbee, or just your camera along, you’ll be in complete bliss. The Victorian-style homes along the park make for a Martha’s Vineyard Full House moment and the landscaping and flowers along the simple park grounds will captivate you. Ocean Park is the ideal spot for sunny afternoons and chilly sunsets.

oak bluffs martha's vineyard


Visit the East Chop Lighthouse

If you’ve rented a car or bikes (or are up for a nice walk), check out the famous East Chop Lighthouse, which is about 2 miles from the downtown Oak Bluffs area. You might even get to enjoy an East Chop sunset if you’re lucky.


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If you’re planning a trip to Martha’s Vineyard in the near or late future, Oak Bluffs is the ideal spot for an action-packed day. Hitting Vineyard Haven or Edgartown is ideal for a scenic trip to MV, but Oak Bluffs is really where it’s happening.


oak bluffs martha's vineyard


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