welcome to martha's vineyard
“Menemsha is an adorable fishing village in Chilmark, and a place very beloved to me because it’s where my family’s home is located. There are many perks to staying in Menemsha: you can walk to restaurants, shops, the beach, and have access to fish straight off the boat. When you’re up-island (Chilmark, Aquinnah, West Tisbury) time tends to pass at a slower pace, and the area is dry (yes, there’s no alcohol sold), which limits the development. Up-island also has miles of bucolic farmland, lush green forests, and beautiful beaches.
Down-island (Oak Bluffs, Edgartown, Vineyard Haven) has more of what most people imagine quaint New England towns to be. There you’ll find bars, restaurants, and movie theaters, and it’s much more touristy.
While my heart will always belong up-island, I recommend visiting all the towns because they’re so different. For example, Aquinnah has celebrated Native American culture and the Gay Head Lighthouse. And Oak Bluffs has gingerbread cottages, back-door donuts (trust me), and the oldest running carousel in America, while Edgartown has a whaling past, cobblestone streets, and white clapboard houses with black shutters. At its widest, the island is only 25 miles across, so seeing each town shouldn’t be a problem.
For the purpose of this guide, though, I’ve focused mostly up-island.”