Just south of Cape Cod, the iconic Massachusetts island of Martha’s Vineyard feels like a place you need a backstage pass for. Like you could travel there on your own, find a good beach, wash down some great seafood with cold beer, and come home toting a big bag of salt-water taffy. But you’d have missed out on all those next-level, trip-making experiences that only long-time visitors and locals are privy to. You know: where to go skinny-dipping or which farmer sells homemade ice cream.
Allow us to introduce you to our Martha’s Vineyard spirit guide, photographer Jessie Webster who’s been making yearly pilgrimages to her parents’ house on the island for 27 years (and frequently documents it on her Instagram account). Below she’s put together a real-deal, locals-only guide to Martha’s Vineyard.
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... For the purpose of this guide, though, I’ve focused mostly up-island.”
“Other than a vacation rental, the Beach Plum Inn is one of the few places to stay up-island. It’s a gorgeous property and the inn itself couldn’t be more charming. Even if you’re not staying there, they have one of the island’s best restaurants—a must in my book.”
“Mermaid Farm in Chilmark is one of my favorites on the Island. I love stopping at their roadside farm stand to pick up fresh veggies, berries, raw milk, and cheese. Make sure to try their mango lassi. In the summer you can also visit them every Wednesday and Saturday at the West Tisbury Farmers Market, along with some of the other best farms on the island.”
“The Martha’s Vineyard Land Bank Commission has worked very hard to preserve some of the most beautiful spots on the island. Luckily you can visit any of their properties from sunrise to sundown, including Ice House Pond. It’s a freshwater pond tucked in a patch of forest near Lambert’s Cove. It is a little tricky to find, but once you do it is so peaceful and the water is much warmer than the ocean.”