How to spend a weekend on Martha's Vineyard

By: Jessica Cho + Save to a List

Dreaming of an idyllic East Coast beach weekend? If you’re thinking of iced coffee in the morning, cape style houses, beautiful beaches, wide open meadows, fresh farm stands, lobster rolls, and summer cocktails… the Vineyard is calling your name.

Plan a weekend trip to this beach vacation destination with more flavor than you might initially expect. Each town has its own unique personality with a number of different activities to choose from. Not so sure where to start? Get ideas from this summer weekend itinerary for Martha’s Vineyard first timers.

Day 1

1. Grab coffee or breakfast at Behind the Bookstore

Behind the Bookstore is a hidden outdoor coffee shop in Edgartown. This charming spot is out of view from the main shopping strip since it’s located behind the bookstore. Once you enter, you’ll be instantly surprised and delighted by the outdoor shaded seating area with adorable overhanging lights. This place is great for grabbing a quick coffee to go, but it’s also open for all three meals. The attached Hemingway Bar is great for unique, specialty brunch cocktails and wine by the glass.

On your way out, pop into the bookstore to browse the shelves and pick up a beach read for later. 

2. Shop in Edgartown

During peak summer months, Edgartown is alive with people, inviting restaurants, ice cream shops, and more. Here, you can find clothing, surf gear, jewelry, books, souvenirs, and beautiful art exhibits. Whether you’re looking for something for yourself, a friend, or a family member, you’re sure to find something you’ll want to take home with you. 

The Blackdog is the perfect place to pick up a shirt, hat, or crew neck. Backwater Trading Co is an awesome place to shop for outdoor apparel, accessories, and fun little trinkets. And one of my personal favorite stores is The Boneyard– a cool surf shop with some seriously soft hoodies, surfboards, and wetsuits in the back.

3. Visit Martha's Vineyard beaches

You can’t visit the Vineyard without visiting one of the many gorgeous beaches. Just like each town has its own flavor, each beach has its own great qualities. There’s a variety of beach vibes, making it easy to find something that’ll be right for you. 

  • South Beach- larger waves for jumping in, boogie boarding, or body surfing - an ideal place to barbecue/have a cookout
  • State Beach- calm, flat waters, spot to jump off the famous Jaws Bridge (yes– the same bridge in the Jaws movie!)
  • Long Point- stunning property in a more hidden, private area in a Wildlife Refuge, ocean and pond side options, very family-friendly, kayak and paddle boarding rentals available on Long Cove Pond, pondside Yoga (Mondays 5:30-6:30pm)
  • Menemsha- calm waters, rocky jetty for fishing off of, fresh seafood shacks nearby for delicious takeout
  • Squibnocket (“Squibby”)- resident beach, rocky, strong waves, favorite spot among local surfers and fishermen, nice to stop and take a look at if you’re passing by in the area rather than for swimming
  • Chappaquiddick- quick 2-minute ferry ride to Chappy (quieter and less populated part of the island), beautiful soft-sand beaches surrounded by picturesque marshland and the bay, more secluded, less crowded

4. Go out to dinner in Oak Bluffs

Since you’ve spent time walking around Edgartown earlier in the day, it’s time to soak in a totally different vibe in the town of Oak Bluffs. OB is known for its colorful gingerbread looking houses and The Flying Horses Carousel, the oldest operating platform carousel in America. This town is also better known for having a more happening night scene.

There are fun waterfront bars like The Sand Bar & Grille or Lobsterville Bar and Grille to relax, enjoy the view, and have a drink. For a family-friendly activity, check out The Barn Bowl & Bistro for gourmet pizzas and a wide selection of entrees. 

Nomans is an awesome barn-style restaurant a short drive from downtown with delicious food options like short rib tacos, tuna tartare, a charcuterie box to share, and summery cocktails. The outdoor seating area is green and spacious and will immediately remind you of a casual backyard party. There’s usually cornhole aka bags in the lawn, twinkling lights hanging from the trees, and live music performances. What could be better?

5. Leave room for dessert

You can’t leave the island without getting yourself a scoop (or more) of Mad Martha’s ice cream– an island classic! It’s rich, creamy, delicious when in need of a sweet, cold treat. Choose from flavors like coconut (my favorite!), lotsa dough, MV sea salt caramel, sinful chocolate, and more!

For the ultimate late night experience, check out Backdoor Donuts for freshly made, piping hot donuts as a decadent nighttime treat. The backdoor is open from 7pm to 12am daily so it’s the perfect place to go after dinner or a night on the town. Try the apple fritter - it's a MUST! It’s huge (great for sharing) and, there’s nothing quite like it!

Day 2

1. Start the morning with fresh produce & baked goods

Martha’s Vineyard has an abundance of picturesque farms sprinkled around the island. Morning Glory is one of my personal favorites– an environmentally sustainable farm that encompasses roughly 60 acres of vegetables and small fruits grown for the whole island community to enjoy. The farm stand, bakery, and kitchen are often busy, especially in the summertime. You can purchase fresh fruits and veggies and pre-made meals, but my go-to has always been their note-worthy banana bread! After browsing around, take some time to admire the beautiful freshly picked flower bouquets right outside the farm stand.

2. Stop at a brewery

Bad Martha’s Brewery is the perfect place to grab a drink and midday snack or meal with friends. The brewery and taproom sit on the Donaroma’s Nursery property, so you’ll be chilling among flowers, plants, and trees. Fresh beers are available daily and you can choose from a number of food options to accompany your bev. Share a charcuterie platter or artisan pizza with friends or munch on something smaller like a soft baked pretzel or caprese salad. Check out upcoming events to participate in activities like trivia night, yoga, or live music performances!

3. Walk to the Aquinnah Cliffs Overlook

Take a drive to the other side of the island to experience a breathtaking vista. This relatively short walk will bring you to sweeping views of the Atlantic ocean, the stunning Aquinnah clay cliffs, and a lighthouse. Park and head uphill to take in the view at the overlook. 

To explore the cliff up-close, walk down to Moshup Beach, nearly half a mile of beautiful coastline right under the clay cliffs. Bring a suit and towel in case you want to take a dip in the ocean! Please respect signs that advise visitors to stay off of the cliffs to protect and preserve the beauty of this natural landscape.

If you’re feeling up for more adventure, check out the nearby Menemsha Hills Reservation Loop, a 3.5 mile hike for more sweeping views of the Vineyard Sound, Elizabeth Islands, and some large ocean front properties.

4. Picnic and watch the sunset at Menemsha Beach

Bring a picnic blanket or some towels and head into Menemsha, a quaint fishing village in the town of Chilmark. It’s a quieter area of the island with a noticeably different feel. Here, you’ll find a few cute boutiques and galleries as well as some fresh seafood shacks. 

Seafood lovers need to try Larsen’s Fish Market, known for their steamers, chowder, and lobster - all served from a take-out window. With your catch-of-the-day in hand, head to the public beach area to set up a spot to picnic with front row seats to a colorful sunset. Since this seafarer town is on the western most part of the island, you can’t pick a better place to get cozy in the sand and watch the sun go down.

There’s something about a New England coastal summer that really is the ultimate vibe. Martha’s Vineyard offers opportunities to lay low and relax, try great food, enjoy ocean views, or hit the town for a more lively evening depending on your mood. For a small island, there’s so much life and many ways to enjoy these hot summer days with the people you love in a beautiful place. Leaving the island on that ferry ride back home is usually a hard goodbye, but a reminder that you can always return to this New England island escape. Start packing!

Expert tip:
Can’t get enough of that creamy Larsen’s chowder? Bring the Vineyard to you and make this recipe at home to be re-transported to a dock or sandy beach, watching the fishing boats coming in for the day or silently taking in the sky’s evening display.

We want to acknowledge and thank the past, present, and future generations of all Native Nations and Indigenous Peoples whose ancestral lands we travel, explore, and play on. Always practice Leave No Trace ethics on your adventures and follow local regulations. Please explore responsibly!

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