If you’re planning a romantic escape and are searching for things to do in Martha’s Vineyard, look no further. This idyllic island off the coast of Massachusetts has it all: scenic beaches, charming towns, and even a hint of old-world glamour.
US Presidents and Hollywood celebs love Marthas Vineyard, Massachusetts namesake of Vineyard Vines preppie-wear, just a few miles off the coast of Massachusetts. And apparently, so did missionaries in the 17th Century. The very first Bible in what is now the United States was printed, not in English, but in the tongue of the local Native Americans – the Wampanoag – in 1663.
Don’t restrict yourselves to MV’s main towns. Head to the Western side of the island (“Up-Island”) that most day trip visitors miss. Bike or take the bus to West Tisbury or Chilmark on pastoral rural roads lined with old stone walls, forsythia and honeysuckle, passing long-horned steer and farm signs advertising “Feta” and other locally grown and made products.
Whether you’re arriving to explore its historical sites, relax on the beaches, or experience its rich culinary scene, Martha’s Vineyard MA offers a diverse array of experiences for every kind of traveler.
Looking for more dreamy weekends around Massachusetts? Check out our Best Romantic Getaways in MA.
Where Is Martha’s Vineyard?
Martha’s Vineyard is an island located off of Cape Cod in Massachusetts, accessible by ferry or small aircraft. Separated from the mainland by Vineyard Sound and Nantucket Sound, Martha’s Vineyard encompasses a diverse array of environments.
From the bustling port towns of Vineyard Haven, Oak Bluffs, and Edgartown to the quieter, more secluded areas “Up Island” like West Tisbury, Chilmark, and Aquinnah, there are six towns and numerous beaches to explore on this 24-mile long by 9-mile wide triangle of land. It’s worth at least a weekend (if not a whole week) to unwind and do it justice.
How To Get To Martha’s Vineyard And Around the Island
Take a Ferry
Forget flying and travel the old-fashioned way. You can catch Steamship Authority car ferries from Woods Hole to Vineyard Haven – the only car-ferry that services Martha’s Vineyard – and the only ferry that runs year round. The ferries below run seasonally only.
To get here faster, HyLine Cruise ferries run from Hyannis (on Cape Cod) to both Nantucket and Oak Bluffs, Martha’s Vineyard. For a multi-island vacay, you can also take the HyLine between Nantucket and Oak Bluffs, MV in season.
Alternately, the Rhode Island Fast Ferry runs from Quonset Point, Rhode Island, to Oak Bluffs.
SeaStreak provides ferry service between New Bedford and Oak Bluffs from the end of April through mid-October, and from NYC (4.5 hours) from May to September
Rent a Bike or Scooter Or Take A Bus
Navigating Martha’s Vineyard by bus is convenient and eco-friendly, offering an excellent way to explore the island’s charming towns and scenic spots without driving. Martha’s Vineyard Transit buses are easiest to use if riders buy a day/multi-day pass and download from the website; this app shows where the buses are located at any given time!
Romantic Things to Do In Martha’s Vineyard
EXPLORE: Vineyard Haven
Martha’s Vineyard Museum/Bunch of Grapes Bookstore
Pick up a bestseller at indie Bunch of Grapes Bookstore – an Obama family favorite. And drop in at the Martha’s Vineyard Museum, for a fascinating insight into the island’s history.
Martha’s Vineyard Playhouse
Here’s an insider tip for celeb sighting (if that’s your thing. Warning – paparazzi are highly frowned upon here, and any expression of celebrity worship is considered overly gauche.) Check out Martha’s Vineyard Playhouse on summer Monday nights at 7:30. New play readings draw entertainment notables who show up to support their friends.
Original Black Dog Tavern
Also, find the largest Black Dog accessories shop. The original Black Dog Tavern opened in Vineyard Haven in 1971, and due to its popularity with tourists (and fantastic location), it’s still going strong.
Black Dog Tavern is not just a dining staple on Martha’s Vineyard; it’s an experience that captures the island’s nautical essence. Known for its hearty, locally-sourced seafood dishes, the tavern also boasts a tempting array of baked goods, including their famous bread, muffins, and pies, all freshly made in-house.
EXPLORE: Oak Bluffs
Ocean Park (Ferry Landing)
If you take the car ferry from Woods Hole, this whimsical sculpture of a family (complete with dog) greets you at Ocean Park. The seaside park has a fountain and gazebo as well.
Flying Horses Carousel
Funky and boisterous, Oak Bluffs is the home of the Flying Horses Carousel, the oldest one of its kind in the United States – built in 1876! Ride it and try to grab the brass ring!
Camp Meeting Association Gingerbread Cottages
And discover the neighborhood that draws architecture fans on guided walking tours. There are over 300 whimsical Gingerbread cottages in Martha’s Vineyard Camp Meeting Association. Notably, this is one of the sites on the African American Heritage Trail on Martha’s Vineyard.
The trail is profound tribute to the island’s African American community, acknowledging their history and significant contributions. Here, the trail specifically recognizes thirty families of color who were forcibly removed from the Campground between 1910 and 1920 due to a policy rooted in racial segregation and white supremacy.
Plaques at the Campground recount this painful chapter, listing the names of the displaced families, thereby ensuring their stories are not forgotten.
Meander Circuit Ave.
Meander up Circuit Ave – Oak Bluffs’ main shopping street – for souvenirs and gifts. If you love unique one-of-a-kind jewelry, don’t miss Stefanie Wolf Designs. Although she sells her creations all over the world, this flagship – and only – brick and mortar store showcases Wolf’s cool glass-bead necklaces, bracelets, and earrings.
Back Door Donuts
On a sun-dappled summer’s day, appreciate these colorful works of artisanal construction, and then at night, stand on line for one of the best donuts ever at Back Door Donuts, open 7 pm to midnight . A straight-up Café & Bakery by day, at night, a “crew of 10 keeps making the donuts until 12am and sells them at the back door.
Island Alpaca
These adorable creatures at Island Alpaca are used for “Fiber Farming,” and this Alpaca Farm is open for tours (and hugs). Two miles from Vineyard Haven within the borders of Oak Bluffs, it’s a quick ride to the lush-lash big-eyed stares of 78 alpacas. With necks like swaying stalks, they are both a tad awkward and delicate after shearing. Owner Barbara Ronchetti is more than happy to introduce you.
EXPLORE: Edgartown
Well-heeled whaling captains built many stately white mansions along the leafy lanes of Edgartown. So, this town remains the preppiest one on Martha’s Vineyard. It’s also home to the Joseph Sylvia State Beach, forever memorialized as the filming site for the iconic movie Jaws. Despite the thriller’s depiction, the actual beach is a tranquil setting for swimming, sunbathing, and picnicking.
South Beach/Katama Beach
On the southern edge of Edgartown, South Beach, also known as Katama Beach, is one of Martha’s Vineyard’s most popular stretches of coastline. Known for its golden sands and rolling Atlantic waves, it’s a beachgoer’s paradise, perfect for sunbathing, swimming, and beach games.
Old Whaling Church
In the late 1700s sea captains established a house of worship where ministers would lead quick one-hour Sunday services rather than the long-winded ones of other island churches. The 1843 Greek Revival Old Whaling Church, with its six massive columns, is still in use and remains a much-photographed Edgartown spot.
Morning Glory Farm
Do drop by Morning Glory Farm for fresh, locally-grown produce, as well as their renowned bakery items; it’s a delightful stop for foodies and farm-to-table enthusiasts alike.
EXPLORE: Chappaquiddick Island
Known for the scandal that nearly took down Ted Kennedy, Chappaquiddick is a large tract of land separated from Edgartown by a few hundred yards. Take the 3-car, 3-minute “Chappy Ferry” drive about 2 miles (on the only road you can), and at a slight bend keep your eyes peeled for a small green sign on the left.
Mytoi Gardens
Take that dirt road to Mytoi, an enchanting 14-acre Japanese garden with walkways, drooping Cherry trees, wooden bridges and the most vocal (some would assume, happy) birds on earth. It is Zen-serene relative to the tourist ruckus in Edgartown.
EXPLORE: West Tisbury
Polly Hill Arboretum
The Polly Hill Arboretum has an incredible backstory. At age 50, in 1957, Polly Hill yearned to create her own tree sanctuary, and so she sent away for seeds from all over the world. Experimental yet pragmatic, Hill planted non-indigenous varieties in the shelter of hearty plants that could protect seedlings from the mighty island winds.
Although no longer with us, Hill left behind a beautiful legacy. These 40 acres of woodlands and 20 acres of trees and gardens can be shared by all. Grounds are open all year, sunrise to sunset. Visitor’s Center open seasonally beginning Memorial Day.
The Field Gallery
This indoor-outdoor art gallery features the work of extraordinary local artists. Far from major Vineyard towns, in West Tisbury, the Field Gallery is a great place to contemplate the juxtaposition of art and nature.
GO: Chilmark
A funny thing about Chilmark: Most of the original Saturday Night Live cast have homes in affluent six-acre zoning Chilmark, where “everyone who doesn’t want to be seen lives” (e.g. Bill Murray, Dan Aykroyd), and where John Belushi is buried.
Chilmark is also the “Birthplace of American Sign Language” – born of necessity. In the 1700’s through the end of the 1800’s, one in three people here were deaf.
Chilmark General Store
If you’re biking the 18 miles (each way) from Vineyard Haven, stop in with others for a surprisingly good pizza at the Chilmark General Store before heading to the town of Aquinnah, home to many of the local Native Americans of that name.
EXPLORE: Aquinnah
Aquinnah Cultural Center
Stop in at the Aquinnah Wampanoag Cultural Center open mid-June to Mid-September to explore Wampanoag history.
Gay Head Lighthouse
You’ll want to capture the grandeur of a sunset from either the red brick Gay Head Lighthouse or the spectacular terra cotta-colored clay Aquinnah Cliffs Overlook point at Moshup Beach.
By the turn of this century, the Lighthouse was on the country’s list of “Most Endangered Historic Places” due to extreme erosion. In 2015, it was relocated 130 ft. from the cliff edge to save it from crumbling into the sea.
Stony Creek Gifts
You’ll find locally fashioned purple and white “wampum” jewelry sculpted from Quahog shells at Stony Creek Gifts right on the path to the lighthouse overlook.
The land you see offshore belong to the string of 16 Elizabeth Islands that extend from here to Cape Cod, the largest of which is Cuttyunk, a speck of oyster-farmers, fishing charters and scrub-brush with 49 full-time residents. From there, the next landmass is Ireland.
VISIT: Menemsha
Larsen’s Fish Market/Menemsha Fish Market
For some of the freshest off-the-boat seafood, peddle over to Menemsha. Not only is this place the poster-perfect New England fishing village, but it also appeared in the movie, Jaws. Both Larsen’s Fish Market and Menemsha Fish Market are good bets.
There’s no place to sit inside these fresh seafood markets. So, order your stuffed or steamed clams, lobster, and broth-like chowder, and then take your meal to the docks out back, hard by the rusted clamming boats. Alternately, walk a block to the beach for yet another unbeatable sunset.
Restaurants On Martha’s Vineyard
EAT/SCENE: Lookout Tavern – Oak Bluffs
This back-deck-like restaurant/bar, the Lookout Tavern, “looks out” over the Oak Bluffs ferry landing and overflows with bar crawlers each warm evening. By day, you’ll be sober enough to appreciate the double-crisped Sweet Potato Fries and pretty decent sushi.
DRINK: Offshore Ale – Oak Bluffs
Grab a handful of peanuts in the shell, then sample a variety of house-brewed beer at perennial Oak Bluffs favorite Offshore Ale.
EAT: Atlantic Fish and Chop House – Edgartown
Right on the Edgartown docks, Atlantic Fish & Chop House serves up great seafood enhanced by stunning harbor sunsets.
EAT: Locals Also Love
In Oak Bluffs: Chef Deon’s Kitchen – Caribbean in the VFW Hall; Sweet Life Cafe for farm-fresh eats; art-filled Red Cat Kitchen; the Barn Bowl & Bistro for pizza; Noman’s for cocktails; Moe’s Lunch for sammies; Midnight Taco near the high-speed ferry landing.
Marthas Vineyard Hotels
STAY: Dockside Inn, Oak Bluffs
Sure, there are larger, more luxurious, and full service hotels on Martha’s Vineyard. But, if you’re going for close-to-the-HyLine-Ferry Dock (and I mean, RIGHT off the dock), cute clean updated rooms, and amenities aplenty – with several good restaurants a minute’s walk away, book a room at Dockside Inn.
The recently refreshed hotel is contemporary and bright. While new owners gut-renovated the hotel in 2012, they hired designer, Tracy Overbeck-Stead (known for her work with the W hotel chain), to create a unique, fun and boutique-y vibe.
And, while rooms are small, they are nicely compact, with clean updated bathrooms, flat-screen TVs and modern, comfy bedding.
Dockside Inn Amenities
Out back, there’s a small yard with firepit, corn-hole game, and secluded large hot-tub.
Raining? Not to worry – the breakfast and treats room is enclosed with tables. Throughout the day, you’ll find PopTarts, instant oatmeal, and fresh fruit as well as pod coffees. Oh – and a freezer full of ice-cream sandwiches and popsicles.
And, the “Beach Gear” shed is packed with everything you need for the beach: chairs, towels, coolers, boogie boards, and more. All complimentary for guests.
STAY: Summercamp by Lark Hotels, Oak Bluffs
The huge Summercamp Hotel looms across the street from Oak Bluffs Harbor and Marina – a 5 minute walk from the high-speed ferry landing – looking as rustic as your average, well, summer camp bunkhouse. Inside though, it’s a different story. Airy, witty, and filled with colorful art, the lobby says otherwise.
STAY/EDGARTOWN: Harbor View Hotel – Edgartown
You can pitch a tent on this exquisite site and be happy. But the Harbor View Hotel is of course far from camping or even glamping. By virtue of its recent renovation, it has risen to the level of luxury “Beachy Chic.”
The Edgartown Lighthouse, a dancer’s leap from the Inn’s wide whitewashed wraparound porch (complete with rocking chairs), glows in the setting sun while boats return to harbor.
Ask for a sizable, beautifully designed Harbor View room in the main building, and you don’t even have to leave your chamber for outstanding pink sunrises and golden sunsets. Suites in private Captain’s Quarters behind the main building include knock-out bathrooms, galley kitchens and sitting room.
STAY/EAT: The Charlotte Inn – Edgartown
The Charlotte Inn is the only Relais & Chateaux property on Martha’s Vineyard. On a side street, it doesn’t offer water-views. But if you wish to vacation like a 19th century whaling captain, this is the place.
Enter into what amounts to an intimate art museum, where exquisite rooms showcase English antiques. Relish American cuisine with French and Italian influence at one of the best (albeit pricey) restaurants on the island, The Terrace. Set within an enclosed conservatory it is “a stunning dining experience,” according to many guests.
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Even although it’s dropped from second to third place, I can see why Martha’s Vineyard is still in the top 3 of the most popular towns in North East America.
Since reading your top 20 list I’ve done some more research and it’s definitely a place I’d love to visit. I’m not too phased about the fact that the rich and famous love it – but I understand why. I’m more interested in the beauty and history of the place.
MV is one of my favorite places – and has been since I was a kid. Thanks so much for reading and commenting! Malerie