How to Experience Martha’s Vineyard Like a Local
Martha’s Vineyard is posh by nature, but the island attitude is decidedly more playful and relaxed.
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Martha’s Vineyard has long been the preferred Massachusetts resort town for the discerning traveler—and a closely-guarded gem by devoted locals who loathe the traffic on Cape Cod and the swarms of tourists on Nantucket. This New England island is distinguished by its historic charm and laid-back atmosphere, as well as its vast and wild natural beauty. Less pretentious than Nantucket and more remote than Cape Cod, Martha’s Vineyard blends its rugged coastal landscape with modern luxuries like charming boutique hotels and sea-to-table restaurants.
Located seven miles east of Cape Cod, the Steamship Authority ferry to the Vineyard from Cape Cod’s Woods Hole takes roughly 45 minutes (around one-third of the time it takes to arrive on Nantucket). The island is also twice the size of Nantucket, with 96 square miles of varied coastal terrain, from the barrier beaches and saltwater estuaries of Chilmark to the coastal bluffs of the fishing village of Menemsha and the dramatic clay cliffs of Aquinnah.
The Vineyard is home to an array of charming villages, including the quaint Gingerbread Cottages of Oak Bluffs and the grand mansions and cobblestone streets of Edgartown. Though this resort town is posh by nature (as is the case with most East Coast escapes), the island attitude is decidedly more playful and relaxed, as evidenced by the whimsical celebrations of the 50th anniversary of Jaws this summer. But visitors can celebrate the film anytime by fishing or jumping off the American Legion Bridge (the “Jaws Bridge”), which was built in Edgartown in 1932.
Whether you’re interested in sampling the freshest local seafood and savoring the best lobster roll on the island or setting out on the most magnificent sunset sail around Katama Bay, we’ve curated a selection of the very best of what Martha’s Vineyard has to offer. From top boutique hotels in Edgartown to remote, wind-strewn beaches in Chappaquiddick, here’s how to explore Martha’s Vineyard like a local.
The Martha’s Vineyard Travel Guide
Where to Stay
Faraway Martha’s Vineyard
- 23 Kelly St, Edgartown, MA 02539
If you want to feel like you’re in the heart of the action, then there’s no better place to stay than Faraway Martha’s Vineyard. It’s located within walking distance of all the shops and restaurants in town, with a vibrant nightlife and dining scene already in place on-site. When the hotel opened in the summer of 2023, on the site of the Kelley House (an establishment that first debuted in 1742 as one of the oldest hotels in the country), locals were concerned. How would this new, buzzy hotel opening square with the spirit of the Vineyard—after all, Faraway’s other outpost was on the much showier island of Nantucket. Despite initial reservations, however, the hotel proved everyone wrong—co-founder Jason Brown grew up visiting Chappy and knew precisely how to infuse modern-day glamour and luxurious amenities into a historic establishment.
The boutique property is composed of 58 guest rooms and suites, as well as shingled cottages, clustered around the central pool and sundeck. (Returning to your cottage after a night on the town, it’s hard not to feel like a local.) The boho-chic decor is inspired by the 1960s and ‘70s, particularly the stylings of Vineyard local (and musical icon) Carly Simon. Visit the outdoor sushi bar, The Pelican Club, or the poolside Snack Shack, and dine on pub fare at the Newes of America.
Harbor View Hotel
- 131 N Water St, Edgartown, MA 02539
Open since 1891, the Harbor View Hotel is a Vineyard classic that’s home to some of the most beautiful water views on the island. Although the location and architecture have remained consistent since the late 19th century, the interior underwent a major renovation unveiled in 2019, including a new penthouse suite, the Presidential Skyhouse Wing, and a redesign of all 117 rooms. The decor remains classic New England: Soft blues and creams, mahogany furnishings, and an oak tree motif that weaves throughout the property. Reserve a Captain’s Cottage to feel like a true local, and make use of the complimentary bikes to cycle to nearby downtown Edgartown. Of course, if you’d rather reserve wheels, the hotel offers shuttles into town via golf cart or Mercedes-Benz. Don’t miss sundowners on the veranda, lawn games, and complimentary yoga on the harbor, as well as the private cabanas poolside. Order cocktails at Behind the View and book a reservation at Bettini, one of the most romantic spots on the island.
Winnetu Oceanside Resort
- 31 Dunes Rd, Edgartown, MA 02539
Head out to South Beach in the Katama neighborhood of Edgartown to stay in Winnetu, where you’ll find classic coastal luxury just steps from the ocean. The property’s 19th-century shingle-style architecture is outfitted with modern conveniences, and the decor is laid-back New England elegance. The 54-key getaway has no shortage of activities, from oyster farm and beekeeping tours to weekly clambakes and daily yoga on the lawn. Complimentary shuttles run to downtown Edgartown, while a water taxi cruises through Katama Bay, delivering guests to dinner. Take advantage of the Two Island Adventure program to book a stay at the hotel’s sister property on Nantucket. Lastly, be sure to dine al fresco at the on-site restaurant, The Dunes, the only dining establishment in South Beach.
What to Do
The Black Dog Tall Ships
- 20 Beach Street Extension, Vineyard Haven, MA 02568
A trip to Martha’s Vineyard is incomplete without setting out to sea for the day. Book a sail aboard the Schooner Alabama, which sets sail for three-hour cruises from the Black Dog Wharf in Vineyard Haven. (We recommend embarking at sunset.) If you’re hoping for a more exclusive cruise, private charters are available to off-island ports such as Nantucket, Newport, Woods Hole and beyond. And if the name is familiar, that’s because the Black Dog brand originated with a sailing captain who sailed tall ships in the 1960s on Martha’s Vineyard and named his company after his beloved black lab-boxer mix. After the cruise, head out to the nearby General Store and Tavern in Vineyard Haven for some merch.
Island Alpaca Farm
- 1 Head of the Pond Rd, Vineyard Haven, MA 02568
For an unexpected afternoon excursion, look no further than the Island Alpaca Farm in Vineyard Haven. The 19-acre farm started in 2004 with eight alpacas, a herd that has since grown to over 70 Huacaya alpacas and two llamas. The delightful property is home to an antique 200-year-old barn and charming gift shop, and is open daily from 10 a.m. to 4 p.m. While just visiting the animals is delightful enough, guests can sign up for various events, including alpaca yoga, which puts goat yoga to shame. The gift shop is replete with quirky treasures, and the photo opportunities are priceless.
Edgartown Harbor Light
- 121 N Water St, Edgartown, MA 02539
The 45-foot Edgartown Harbor Light is one of the most iconic sites on the entire island. Built in 1828, it marks the entrance to Katama Bay and Edgartown Harbor. Stroll through The Dunes to the lighthouse and drink in the surrounding scenery, or pay $5 to climb to the top and witness spectacular views of Chappaquiddick and Cape Cod. A quick walk from Main Street in downtown Edgartown, the lighthouse is open Friday to Sunday from 10 a.m. to 4 p.m. The lighthouse is under the stewardship of the Martha’s Vineyard Museum, in Vineyard Haven, which is another spot to consider visiting during your stay—especially on a rainy day. But for summer afternoons, we suggest heading to nearby Lighthouse Beach to sunbathe on this picturesque slice of sandy coast overlooking the Outer Harbor.
Chappy Ferry
- 53 Daggett Ave, Edgartown, MA 02539
Board the ferry from Edgartown to Chappaquiddick, known as “Chappy” by the locals. Though the islands are a mere 527 feet apart, the rural landscape of Chappy is transportive—you will feel you’ve entered another world. The island is accessible year-round via the Chappy Ferry, which runs from 6:30 a.m. to midnight, so you have ample time to explore on a day trip. The two-minute ferry ride across the channel is only a $5 round-trip fare for passengers, or $17 if you’re bringing your own wheels. The rugged island has just one main road, which is roughly four miles long and leads southeast from the ferry landing, as well as a single, one-room general store. But don’t let the remoteness fool you—once you’ve arrived, the world is your oyster, with activities including swimming at East Beach, walking the coastline at Chappy Point, and exploring the various wildlife refuges, such as Wasque and Cape Poge. Over a thousand acres (nearly a third of the island) are conserved, fostering an idyllic setting for picnicking, hiking and birding. Simply put, Chappy is magic. There’s no better place to venture into the wild.
Where to Eat
The Seafood Shanty
- 31 Dock St, Edgartown, MA 02539
Head to the docks of Edgartown for a waterfront meal al fresco at The Seafood Shanty, a casual favorite that’s been serving lobster rolls and mouthwatering Painkillers for more than 50 years. The patio overlooking the harbor is an ideal spot to catch the sunset, while the people-watching is unparalleled at any time of day. Aside from the lobster roll, other popular items include the lobster quesadilla, chowder, fried clams and crazy tuna roll, all made with fresh seafood. The shanty serves up a low-key ambiance befitting its name, and walk-ins are welcome. We recommend a reservation for the peak summer season, especially if you’re looking to dine indoors.
Bettini
- 131 N Water St, Edgartown, MA 02539
For a fancier option, consider reserving a table at Bettini, the fine dining restaurant at the Harbor View Hotel, five minutes from Main Street. The historic shingled property is situated on a picturesque expanse of lawn overlooking the harbor. Arrive early for your dinner reservation to catch the sunset from one of the Adirondack chairs on the wraparound porch, with a cocktail in hand—we suggest a margarita; the mango and guava flavors are particularly popular. The elegant, nautical-chic bar and restaurant boasts leatherbound seating and expansive windows, capitalizing on the view of the ocean and the Edgartown Harbor Light. Though the decor is upscale, the dress code is resort casual—jackets not required, but flip-flops not recommended. Reservations, on the other hand, are recommended, especially if you’re visiting Martha’s Vineyard during high season. The wine selection is extensive, and the upscale American cuisine includes clever twists on seafood classics; try the pepper-crusted swordfish or lobster bucatini.
Beach Road
- 79 Beach Rd, Tisbury, MA 02568
For true sea-to-table cuisine, check out Beach Road on Lagoon Pond in Vineyard Haven. Chef Frank Williams works closely with local fishermen, and the seasonal menu specializes in seafood favorites. The lobster roll is always a top choice, but whether you order it “Down Island” (bacon, peas, lemon aioli) or “Up Island” (just the butter and the bun) is a matter of taste. The restaurant is, of course, located up island—down island is home to the more populated, touristy villages, like Edgartown. The nautical decor also reflects the menu, with interiors inspired by Martha’s Vineyard's shipyards and maritime history. Be sure to book a reservation in advance, as the eatery is popular year-round, but especially in peak season.
And a Few More…
Breakfast on the Vineyard is something of a specialty, with a wide selection of cafés and bakeries catering to early risers. Check out Dock Street Coffee Shop, Back Door Donuts, or MacPhail’s Corner Cafe for a grab-and-go selection. Another newer option is Catboat Coffee, which also serves delicious Lebanese pastries in Vineyard Haven. Blackbird Cafe offers a more elevated morning menu, while Among the Flowers includes Bloody Marys and frosé alongside its cappuccinos and chai lattes. To satisfy your sweet tooth later in the day, check out the homemade ice cream at Mad Martha’s or sample the local flavors at Murdick’s Fudge, which has been operating on the island since 1978. Lastly, the Outermost Inn serves up fireside dining and gorgeous views of the rolling hills of Aquinnah.
Where to Shop
Martha’s Vineyard Glassworks
- 683 State Rd, West Tisbury, MA 02575
For a custom souvenir from your stay on the Vineyard, head up-island to visit Glassworks, an artisanal design studio with countless colorful treasures. The Shop was opened in 1992 by seasonal residents who converted the historic West Tisbury property into a glass studio and viewing space. The lower gallery showcases an array of glass art, while the upstairs gallery spotlights one-of-a-kind works by rotating artists. The shop is open Tuesday to Sunday from 10 a.m. to 4 p.m., although hours are seasonal. Check to see if there are any upcoming events during your stay on the island.
Nell
- 19 Main St, Edgartown, MA 02539
Main Street in Edgartown is home to an array of upscale shops filled with items you simply can’t find at home, and we suggest beginning your journey at Nell. The women’s clothing boutique is dedicated to supporting local businesses and ethically sourcing all its materials, offering unique pieces and personalized styling in-store. (Plus, the two labradoodle shop dogs, Bosun and Captain, are simply adorable.) Continue your pursuit of retail therapy via resort-wear at additional local storefronts in downtown Edgartown, including Rags and The Shop, which also serves artisanal coffee. And for that perfect Chappy sweatshirt, head over to Shirt Tales, which got its start by printing Jaws T-shirts in 1975.
Where to Drink
The Port Hunter
- 55 Main St, Edgartown, MA 02539
Check out the craft cocktails during happy hour at The Port Hunter, an always-happening bar and restaurant on Main Street in Edgartown. The raw bar is unparalleled, with a fresh selection of oysters and mussels to complement your beverage of choice. The brick-walled space grows ever more popular during the peak season, especially on weekend nights, so head there early to avoid a line. Check out the live music, and plan to stay awhile—the scene grows ever more entertaining as the night progresses. And for a late-night bite, head over to Backyard Taco on Winter Street (this Vineyard establishment stays open until midnight).
The Ritz Cafe
- 4 Circuit Ave, Oak Bluffs, MA 02557
Set out for Oak Bluffs to check out the historic Ritz Cafe, which has been serving up live music and even livelier crowds since 1944. This is a dive bar beloved by both weekend visitors and locals alike, and the small venue makes for a more intimate and energized environment, especially during one of the many events the cafe hosts throughout the year (off-season included). While visitors should consult the event calendar for live musical acts, but you needn’t recognize any of the bands to know you’ll have a great time. The disco balls hovering above the dance floor are perfect for a wild weekend night, but the Ritz is also popular during sporting events. And, if you happen to be in the room for one of their iconic karaoke sing-a-longs, well, no need to worry about singing in tune—the more raucous, the better.
And Honorable Mentions to…
The Alley and the Lookout Tavern are additional watering holes to check out while in Oak Bluffs, while the combination of craft cocktails and homemade ice cream makes the Alchemy, in Edgartown, simply irresistible.