News

Oct 27, 2023

The Best Things to Do on Martha's Vineyard This Summer, From Sleek New Hotel Bars to Historic Sailing Events

By Todd Plummer It’s not that New Englanders don’t take change well; it’s that

By Todd Plummer

It's not that New Englanders don't take change well; it's that we have a lot of history up here, and we’re proud of it. So anytime something happens on a small island such as Martha's Vineyard, it's bound to turn heads and raise some eyebrows. The island has always had a special place in our hearts as a summer colony—and has received some national attention lately due to the Bravo spinoff Summer House: Martha's Vineyard. And since we all learned the value of outdoor space during the pandemic, the Vineyard has become even more of a treasured getaway.

Whereas some years feel like tidal waves of change are taking over the island, this year isn't one of them. There's some hotel news that's absolutely worth knowing, and a full-blown roster of events and festivals—some of which are returning to their original scale for the first time since the pandemic. Otherwise, you can (thankfully) still expect those sleepy, languid, New England summery vibes that keep people coming back to the Vineyard year after year, generation after generation. If you’re asking us, here are the things to keep on your radar if your travel plans bring you to Martha's Vineyard this summer.

All listings featured on Condé Nast Traveler are independently selected by our editors. If you purchase something through our links, we may earn an affiliate commission.

The historic Kelley House in historic Edgartown is now Faraway Martha's Vineyard.

The big hotel news on the island this summer is the arrival of Faraway Martha's Vineyard, a total renovation of the historic Kelley House, right in the center of historic Edgartown. Much like the first Faraway location on neighboring Nantucket, the ethos of this one is eclectic, yet rooted in mid-century styling. The rooms feature fabulous details such as Italian linens from Bellino, luxury bath amenities from Byredo, and in-room mini fridges. And longtime Vineyard goers will be pleased to find out that the main-floor pub, the historic Newes from America, is still very much the same—barring a few subtle design refreshes and several welcome updates to the menu. Overall, it's a flashy new hotel that even the saltiest Edgartown locals will be able to get behind.

Kitty-corner and a few doors down the street, Lark Hotels recently added The Coco to its Edgartown Collection, a portfolio of five small-scale hotels, all just steps from each other in downtown Edgartown. Located in a historic sea captain's home, each room at The Coco is different from the next, making it feel less like a hotel in the traditional sense and more like your most fabulous friend's Vineyard estate. You won't find any stereotypical shiplap or nautical designs here; Boston based designer Rachel Reider reimagined the property in a lush palette of jewel tones and textured finishes. And best part of The Coco's non-hotel atmosphere? You still get all the amenities of a hotel stay, including beach towels and chairs for daytime excursions, fantastically comfortable mattresses, and Lark Hotels’ signature small-plates breakfast for a quick, complimentary bite before starting your day.

And just a few minutes outside of the commotion of downtown Edgartown, set on 11 bucolic acres by South Beach, family-owned Little Gem Resorts’ beloved Winnetu Oceanside Resort is gearing up for a slight facelift. The lobby, concierge and game room are getting a zhuzh from New York City interior designer Michael Kramer, who describes the colorful update as "retro meets American summer, very 70's, disco fun for sure, but not disco balls." On an island where quintessential New England everything is abundant, that sounds like exactly the way to shake things up while still honoring the Vineyard's nostalgic, all-American roots.

Edgartown Race Weekend will bring together sailors from across the country June 15-17 for spectator events including the 85th annual ‘Round-the-Island Race—one of America's oldest distance sailing races.

You’d think the Vineyard was an island ten times its actual size, based on the number of events scheduled there for this summer. Here are a few selections that will help you get a sense of this island's character.

Whenever you’re visiting, make sure to pencil in some time to stop by Grange Hall in West Tisbury, where the Vineyard Artisans Festival operates on Sundays from Memorial Day through September, in addition to Thursdays in July and August. It's a wonderful opportunity to explore the island's thriving community of artisans, with a range of souvenirs and gifts to bring home, from sustainable wooden bowls carved from Martha's Vineyard trees, to bunches of dried lavender, as well as ceramics and jewelry.

Be sure to check out the second annual Oak Bluffs Pride Parade, a short march which concludes with an afternoon of festive dancing at the Ocean Park gazebo (June 10). The following week, Edgartown Race Weekend brings together sailing aficionados from across the country for a number of events that are fun for spectators and participants alike, including the 85th annual ‘Round-the-Island Race, one of America's oldest distance sailing races (June 15-17). That same weekend, to celebrate Juneteenth, a replica of the historic schooner Amistad—that became famous after a group of enslaved Africans led a successful revolt—will drop anchor in Oak Bluffs and offer free public tours (June 16-19).

Later in the summer, keep an eye out for more sailing races at the Vineyard Cup Regatta (July 7-9), and meet some of your favorite authors at the Martha's Vineyard Book Festival, returning to an in-person format for the first time since 2019 (August 4-6). Round out the summer with Beach Road Weekend, a surprisingly cool music festival with acts including Bon Iver, Patti Smith, Mumford & Sons, and Dispatch (August 25-27).