Towns

Oak Bluffs

Oak Bluffs is where WhatsUpMartha spends a lot of time. If you’re looking to go out at night, Oak Bluffs ‘OB” for island slang is where it’s at. You can cruise Circuit Avenue, where the bars and restaurants are a plenty and mingle with some of the islands best visitors and residents. Why? Because they’re out! We highly recommend OB on weekends and nights, but if you’re a day timer, it’s got all the perks that you’re looking for on a nice hot, summer day.

Edgartown

The more quaint and colonial of Martha’s Vineyard, you’re going to find white fences galore, classy dining, boutique shopping and the upper part of society. But, don’t let this fool you, there are always some rebels in the mix. Edgartown, may be one of the most pretty towns on the island, but they too know how to have a good time. There are a few great bars and restaurants we highly recommend and of course, some epic spots to catch a smooch or enjoy a bottle of wine. It’s all about the vistas.

Menemsha

Menemsha is an adventure to find, but when you come around the bend in the road on this small fishing village, you’re going to know why it’s so spectacular. The sunset for one, is by far one of the most spoken about on island. It’s epic. After that, there’s a great lobster/fish joint (Can you guess the name?) that sells boiled lobsters and raw shellfish that you can munch on while watching time pass, or even better, the commercial fishing boats slump up and down with the tide. If you’re into no frills, no table cloths, no nonsense, check out Menemsha.

Aquinnah

The Indian Wapanoag tribe have inhabited this land for centuries. Be sure to check it out, but as far as What’s Up; you need not know anything besides the fact that the clay cliffs are out of this world. The sight is pristine, the beach below the cliffs, has a distinct personality found in very few other places. Check it out for sure, picnics on beach encouraged. You know what to do.

Vineyard Haven

We have to tell you now, but Vineyard Haven is a dry town. That means after Prohibition ended, Vineyard Haven said “Hey, that wasn’t such a bad idea, let’s keep it up!” So, they did. But, don’t let it fool you. There’s scores of great shops, packed with things you’ll need and of course, some awesome restaurants that have really had fun with the Byob policy (bring your own wine too!). Either way, we’re pretty confident you’ll find the secret spots in Vineyard Haven we love…if you’re lucky we’ll tell you!