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). “Since I grew up in Ojai, I’m so grateful I got to experience those New England summer nights, complete with clambakes and fireflies,” the now-L.A.-based Webster says. “It’s very nostalgic to me, not to mention stunningly beautiful.”
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.
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.”
“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.”
“Menemsha Beach has the best view of the sunset, which is not lost on anyone who visits the island. Grab dinner to-go at one of the many restaurants or stands like Menemsha Galley (where the clam chowder and lobster roll, above, are from), The Homeport, The Bite, Larsen’s Fish Market (where the steamers are from), or Menemsha Fish Market, then walk down to the beach for a sunset picnic with friends and family.
Pro tip: Make sure to leave yourself plenty of time to find a parking spot and potentially wait in line, because they can be long. Bring your own beer or a bottle of wine because you won’t find alcohol up-island—it’s completely dry.”
“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.”
“Lucy Vincent Beach is only open to Chilmark residents with a permit/beach sticker, which is one of the reasons it’s so special—so befriend a local or rent a house that comes with beach access! Don’t get me wrong: In the summertime it can be packed, but if you walk past the clay cliffs it’s usually less crowded. While I love this beach and spend the most time here, it makes me sad to return each year and see how quickly the beautiful red-clay cliffs are eroding. It’s a reminder that we must care for our planet and no landscape is immune to the effects of our changing climate.”
“While wondering around Menemsha I always make sure to stop at Oversouth Antiques. They have a wonderful collection of nautical knickknacks, kitchenwares, and paintings. I like bringing a little New England back home with me to L.A.”
“The Allen Farm Sheep and Wool Company is the oldest working farm on the island. I like to stop by to visit their shop where they sell blankets, sweaters, and skeins of wool, and to see the horses, donkeys, and, of course, sheep. This past summer my friends and I fell in love with an adorable runt named Midge.”
You travel because…Nothing gives me quite the high that traveling does. I love exploring and experiencing new things. I also think that changing scenery appeals to my photographer’s eye.
Your travel style in five words…Researched, but not planned. That was four words, ha! I like to research ahead of time, making a list of landmarks I’d like to visit and restaurants I’d like to try, but I’m always open to that list changing once I arrive.
Coolest place you’ve been recently…I went to Maui and Kauai with two friends to shoot for the tourism board. Both islands are so beautiful but in totally different ways. I think driving the Road to Hana and seeing the Napali Coast from a door-less helicopter are two of the most memorable things I’ve ever done.
Dying to visit…Morocco. I am endlessly inspired by the architecture, the tile, and the colors.
Travel advice you swear by…When you’re packing, roll your clothes up instead of folding them. It saves space in your suitcase and your clothes will arrive way less wrinkled.
That thing you always pack…A hat. It is, after all, my favorite accessory.
Everywhere you go, you check out the…Local cuisine.
What you bring back from every trip…About a million photos. I can’t help myself!
Your #1 tip for taking better photos…Wait until the light gets good right before sunset, or, even better, wake up early for sunrise when there are fewer people around to get in the way of your shot.
Your wackiest travel ritual…If I’m going on a long flight I wear compression socks. My friends definitely make fun of me but they stop my ankles and feet from swelling during the flight.
Phrase you try to master in the local language…Coffee and thank you.
Dream travel partner in crime…Someone who likes to explore, take pictures, and eat as much as I do. Someone who is considerate and can laugh things off. I’m pretty much describing most of my friends. Not every friend makes a great travel companion (I’ve learned that the hard way), but most of mine are!
Current favorites on Instagram…@casualtimetravel and @davidkitz. They have such a unique perspective. I love how they see L.A.
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