48 Hours on Martha’s Vineyard

What would you do with 48 hours to spend in the sun and on Martha’s Vineyard? We asked local influencer Annah Todd for her recommendations on how to make the most of your time on the vineyard.

Martha’s Vineyard is one of those rare well-known vacation destinations that not only meets your expectations – it actually exceeds them. To take full advantage of the island itself, you will need a car, and if you can, find your way onto a boat. The travel to Martha’s Vineyard itself is an easy 40-minute ferry ride from Woods Hole or Falmouth, and there are lots of ferry options depending on when and from where you are coming.

Martha's Vineyard

Photography shot by Jack Callahan

I visited Martha’s Vineyard for a weekend at the beginning of June. The weather was perfect for breezy linen tunics and flowy silk dresses – and we even managed to squeeze in some time at the beach! Below are my recommendations for the best Martha’s Vineyard activities. If you can, stay longer than a weekend.

Cliffs and Beaches

Aquinnah, MA

The clay cliffs of Gay Head are striking. Unlike anything I’ve seen on the east coast before, the cliffs are a vibrant terracotta color. They are protected, but you can get a stunning vantage point from the Gay Head Lighthouse.

Annah Todd on Martha's Vineyard

Photography shot by Jack Callahan

For an even better view, I recommend walking down to Moshup Beach.  Moshup Beach is public so depending on the time of year you visit, parking may or may not be an issue, so consider the time of day and season. The cliffs and beach are located on the most western point of the island, resulting in an unbelievable sunset.

Annah Todd on Martha's Vineyard

Photography shot by Jack Callahan

Chappaquiddick Island

Chappaquiddick, MA

Rent bikes and take them on the small Chappy Ferry, to Chappaquiddick from Edgartown.

It’ll cost you $6/person round-trip and the ferry ride takes about five minutes. The ferry’s slogan is endearing and fitting: “Back and forth between two worlds – 527 feet apart.” Almost 1,000 acres of land is preserved on Chappaquiddick Island by The Trustees of Reservations, and the island truly feels like an entirely different place than the bustling streets of Edgartown. While you cannot really go wrong with anything on Chappaquiddick Island, East Beach (otherwise known as Leland Beach) in the Cape Poge Wildlife Refuge is my absolute favorite. With salt marshes, 14 miles of trails, and seven miles of remote beach, I highly recommend packing a snack and enjoying the isolated and peaceful excursion.

Annah Todd on Martha's Vineyard

Photography shot by Jack Callahan

Ice House Pond

West Tisbury, MA 02568

I would never have found this swimming spot if an old friend who summers on the Vineyard hadn’t told me about it. He described it as “unusual and difficult to get to,” so naturally, I knew we had to check it out. Ice House Pond is a secluded pond inside Martha’s Vineyard Land Bank Commission preserve and it’s a well-worth trek off the beaten path. When you arrive, parking is extremely limited (only four spots). Since there is no beach at the swimming hole, it’s a destination more reserved for adventure seekers than families, but there is a perch where you can slip into the crystal clear freshwater and enjoy a long swim. The pond’s name comes from its industrial past: the Vineyard Ice Company, from 1908 to 1953, ran an ice-harvesting operation out of the pond.

Annah Todd on Martha's Vineyard

Photography shot by Gretchen Powers

Back Door Donuts

5 Post Office Square, Oak Bluffs, MA 02557

I was hesitant to try Back Door Donuts, I will admit. Everyone told me to go, and frankly, I’m more of an ice cream kind of girl rather than donut. However, I acquiesced and found myself waiting in a 40-person line one evening, and boy, was it worth it. Open only at night (7:30 PM – 1 AM), the donuts were incredible. The kind woman working behind the counter recommended the apple fritter but after seeing the magnitude (they are approximately the size of a football), I opted for the classic chocolate glaze. Worth every bite.

Behind the Bookstore

46 Main St, Edgartown, MA 02539

While I cannot vouch for Behind the Bookstore’s food offerings, I can tell you that their espresso drinks are fantastic. We went right when they opened, around 7 AM, and ordered cortados and sat under the tent. The sun was so bright and the foliage around the tent was so lush, it had a very ethereal feeling to it.

Annah Todd on Martha's Vineyard

Photography shot by Jack Callahan