Welcome to Fifty Grande’s Best of the U.S. Bucket List series. This is your one-stop travel guide to the best, most unique and quintessential experiences of a city, state or event. Want to know how to “do” Martha’s Vineyard? We’ve got you covered. Curated by experts, vetted by in-the-know locals, this is all you need to have the best trip ever. If we’ve written a Bucket List, we recommend you go. If it’s on this list, it’s the best the city has to offer right now. Consider this your one-stop answer to “What are the best things to do in Martha’s Vineyard?”
The native Wampanoag people who first inhabited this nearly 100-square-mile island originally called it Noepe, which aptly translates to “in the midst of the sea.” These days, about 5,000 Wampanoag still reside around New England, and they’ve been joined by generations of revelers and residents who flock here for an array of woodsy and beachy nature. No matter what outdoor activity you’re itching for, whether in its multitude of peaceful forests or copious beaches, you can partake with a sense of escape that only an island can offer.
While there aren’t any actual vineyards here, the community has earned a worldwide reputation as a premier vacation destination thanks to its aforementioned nature, vibrant food and drink scene and a land awash in quaint hotels and picturesque homes. It’s no wonder everyone from Oprah Winfrey to the Kennedys and Barack Obama (who owns a house here) have fallen in love with the sea-locked paradise. But don’t take their word for it: whether it’s summer peak or a spring or fall shoulder season, venture out into the midst of the sea and see it with your own eyes.