Off the Southern coast of Cape Cod lies the island of Martha’s Vineyard. Just seven miles offshore, ‘The Vineyard’ as locals and regulars call it, feels like a world away from hectic everyday life thanks partially to the 45-minute ferry ride through Vineyard Sound. There are six towns, each with its own personality, ranging from rustic and rural to cozy and chic. Best of all, you don’t need a car to get around Martha’s Vineyard, and in the summertime, you’re better off without. Whether spending a day, weekend, or entire week, Martha’s Vineyard never disappoints.
From Ferry to Carousel
The ferry from Woods Hole comes to port at one of two places: Vineyard Haven, the year-round ferry terminal, or Oak Bluffs, the preferred hangout for locals and regulars thanks to a lively yet laid back reputation built around great restaurants and nightlife. Here, you’ll find Flying Horse, the oldest platform carousel in the country, moved from Coney Island to Oak Bluffs in 1884. It’s even been designated a national landmark by the U.S. Interior Department. Still in operation today, the decorative horses allow riders to reach for a lucky brass ring.
Once your equine fun is done, take the hour or so bus ride further off the beaten path to Aquinnah, to see stunning Gay Head Light set high upon the Gay Head Cliffs. Located in the truly tropical looking westernmost part of Martha’s Vineyard, the lighthouse guards a dangerous section of underwater rocks known as “Devil’s Bridge.” It’s open to the public for self-guided tours and offers sweeping views of the island from all angles. The area surrounding Gay Head is comprised of several shops, museums, snack bars and a restaurant, making this a full afternoon destination.
Set the scene: It’s just about dusk on a warm June day, you’ve been jaunting around the Island for the past 10 hours, spotting lighthouses, snacking your way through the island towns, and now you’re ready to just lay back, relax and take a moment to enjoy the beauty. Cue the fishing village of Menemsha, which happens to be the best spot to view the sunset on all of Martha’s Vineyard. The area is picturesque day or night with fishing boats and shacks dotting the marina. At sunset, crowds gather with picnic baskets filled with wine and cheese to watch the stunning display Mother Nature puts on every single night.
One of the most worthwhile hidden gems on Martha’s Vineyard—and also the perfect stop-off on the way to your Menemsha sunset viewing adventure—is the farm stand at the minimalist Grey Barn and Farm in Chilmark. Really more of a cottage, of sorts, it’s located just off the road and offers a wide range of goods, including eggs, meats and signature farm-made cheese. Grab a sampling of their Prufrock, Eidolon, or Bluebird cheeses, any (and all) of which make a stellar addition to any picnic basket. This rustic spot runs on an honor box system, so bring cash and be ready to make your own change.
Back in Edgartown the Martha’s Vineyard Museum is a great spot to spend a few hours out of the sun on a hot day, or to dodge a passing summer shower. The highlight of the museum is the first ever Fresnel Lens—named after creator Augustin Fresnel—the original 1856 lens from Gay Head Light. Used in the lighthouse for over a century, the lens employs hundreds of prisms arranged in a beehive shape, refracting and reflecting the light from an oil-burning lamp. It creates a single beam that can be seen 20 miles away. It’s one of only 39 original order Fresnel lenses left in the country, and it’s the most complete.
Arguably the coolest restaurant in Edgartown, The Port Hunter relies on seasonal foods to create unique twists on comfort classics, and also offers new and inventive American-style dishes. As you would expect, there are always seafood dishes and raw bar items on the menu: This is Martha’s Vineyard, after all. The physical space is rustic and trendy with butcher paper, mason jar glasses and several communal tables in addition to individual setups. During the summer there’s often live music, and the place can get pretty crowded during dinner, so arrive early and stake a claim at the bar where you can order the full menu and imbibe on local craft beer and excellent hand-mixed cocktails.
The Offshore Ale Co. at Oak Bluffs is an "eat and do" combo. The actual brewing of the beer happens behind the bar, while the loft space acts as a dry storage and tasting room. Tours happen on the weekends and calling ahead for reservations is recommended. Food at Offshore is outstanding with an expansive menu of hearty favorites. If you hit it right, they’ll be serving up baked potato pizza topped with bacon, cheese, sour cream and—you guessed it— potato. Pizza by the slice is available Fridays and Saturdays until 10 pm.
Where to Stay
The Vineyard Square Hotel sits smack in the middle of Edgartown within easy walking distance to Port Hunter and Edgartown Lighthouse—one of the island’s five lighthouses—located at the end of North Water Street. The cozy king rooms are compact and affordable, and the property also has a wraparound front porch that gets lively in the evening.