Martha's Vineyard Travel Guide: Oak Bluffs

Martha's Vineyard is the perfect weekend getaway (or even a day trip). After all, it's only a ferry ride away. We love Martha's Vineyard and are excited to launch this three-part travel guide so that we can share all of our favorite places with you gals! Parts 2 and 3 of the guide will cover Edgartown and Vineyard Haven - so keep an eye out for those in the coming weeks. But now, let us introduce you to Oak Bluffs! 


You can catch a ferry to the island from a couple different locations; Woods Hole, Hyannis, Falmouth, New Bedford, as well as some Rhode Island, New York, and New Jersey locations. Which ferry to take is up to you:  do you prefer longer drives? Longer ferry rides, cheaper tickets, or you need a ride to the ferry? The shortest ferry ride is the Island Queen ferry ($20 round-trip) from Falmouth to Martha’s Vineyard (it only takes 35 minutes), but it’s almost a 2 hour drive from Boston to Falmouth. Parking is $15/day. Another option is to catch the Seastreak ferry ($70 round-trip) from New Bedford, which is only an hour and 15 minute drive from Boston. They do offer transportation from Boston to New Bedford for an extra fee. The Seastreak ferry takes about an hour to get to Martha’s Vineyard and parking is from $13-$25/day.

The boats drop off in two MV towns: Vineyard Haven and Oak Bluffs. So, if you're planning to spend your vaca in Oak Bluffs, its obviously easiest to catch a ferry that goes straight there. If you go to Vineyard Haven, it isn't the end of the world -  rent bikes and ride them to OB. Car rentals are available as well. Surprisingly, there’s also public transportation on Martha’s Vineyard in the form of the VTA bus! 


Island Bar and Grill

Island Bar is the place to go for your typical pub grub with some nautical flare. They feature has a variety of seafood options on the menu: fried scallops, fried shrimp, fish & chips, fish wraps and delicious lobster rolls. No visit to Martha's Vineyard is complete without a lobster roll!

Lookout Tavern

If you’re looking for an after dinner spot, head to Lookout Tavern. This is our fav spot in OB for nightlife and good drinks. Hint: order the sangria!


Nancy’s is a great combination of both of the above. They have great food, but they are best known for their signature cocktail: the dirty banana. This sweet frozen treat is equal parts naughty and nice making for the perfect vacation indulgence. 

Mad Martha's Ice Cream

Now for dessert! If you have a sweet tooth, finding good ice cream is always priority. Luckily they have that covered on the island. Mad Martha’s Ice Cream is the place to go, they have two locations - Oaks Bluff and Edgartown.



The Black Dog is a great store for those seeking Martha’s Vineyard nostalgia. Visit On Kennebec boutique for trendy clothes and chic accessories. There's also a Johnny Cupcakes location in OB which is another cool shop for snarky  graphic tees. There are plenty of places to get MV-branded clothing, but we highly suggest Tease Outlets for good quality and price.


Definitely go for a swim while you’re on the island! The water feels amazing, especially after a bike ride around town.

Oak bluffs gingerbread cottages

Oak bluffs gingerbread cottages

Explore & Learn

If it is too cold to swim, visit the gingerbread houses near the Tabernacle. Most of the shops and restaurants a walkable distance from here. Martha’s Vineyard also has a museum that is a great indoor activity, or plan to tour some of the lighthouses on the island. Or go to Pirate Adventures (it’s for kids but it’s still fun)! 


Colleen Gordon is a content contributor for JUGs, but also shares her views over at her blog Here She Stands. You can follow Colleen on Twitter @here_she_stands.