A Couples’ Guide to Things to Do in Martha’s Vineyard

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.

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.

Where Is Martha’s Vineyard?

Martha’s Vineyard is an island located south of Cape Cod in Massachusetts, accessible by ferry or small aircraft. Known for its pristine beaches, picturesque landscapes, and charming small towns, the island is a popular destination for both short getaways and extended vacations. 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 like 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.

Edgartown Harbor Sunset Marthas Vineyard
Edgartown Harbor Sunset

Romantic Things to Do In Martha’s Vineyard

Nantucket Ferry from Woods Hole MA

DO: Take a Ferry

Forget flying and travel the old-fashioned way. You can catch Steamship Authority car ferries from Woods Hole to Vineyard Haven and foot/bike ferries for day trips from Falmouth, MA, and Quonset Point, Rhode Island, to Oak Bluffs.

There are even 5-hour ferries from New York City. Savor the trip – you’ll feel as if you are on vacation once you leave the mainland.

TRANSPORTATION: 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. The Vineyard Transit Authority provides frequent service, making it easy to hop on and off at key destinations.

Time to Read clock Bunch of Grapes Bookstore Martha's Vineyard MA
Time to Read Clock by Bunch of Grapes Bookstore

EXPLORE: Vineyard Haven

Vineyard Haven is so arts and crafty you’ll stumble on the kind of knickknacks that trendsetters find appealing. Check out Rainy Day and Night Heron Gallery, which features one-of-a-kind goods made by local artists.

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.

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.

Black Dog Tavern Marthas Vineyard MA
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.

Flying Horses Oldest Carousel in USA Marthas Vineyard MA

EXPLORE: Oak Bluffs

Funky and boisterous, Oak Bluffs is the home of the Flying Horses Carousel, the oldest one of its kind in the United States. Ride it and try to grab the brass ring!

Marthas Vineyard Camp Meeting Assoc.

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.

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 7:30pm to 1am. A straight-up Café & Bakery by day, at night, a “crew of 10 keeps making the donuts until 1 am” and sells them at the back door.

Chappaquiddick MA

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.

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, Edgartown MA

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.

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.

VISIT: 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 Chappaquiddick MA
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.

TOUR: Western Part of Martha’s Vineyard, aka “Up-Island.”

Most day tourists don’t see this side of the island. 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.

Island Alpaca Marthas Vineyard

Stop in at Island Alpaca

These adorable creatures are used for “Fiber Farming,” and this Alpaca Farm is open for tours (and hugs). Two miles from Vineyard Haven, 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.

Next 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 West Tisbury Marthas Vineyard MA

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.

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.

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 Aquinnah (formerly Gay Head), owned by the local Native American tribe of that name.

Stop in at the Aquinnah Wampanoag Cultural Center open Memorial Day to Labor Day to explore Wampanoag history.

Don’t Miss the 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.

Gay Head Lighthouse Marthas Vineyard MA

FYI – the Lighthouse is on the country’s list of “Most Endangered Historic Places” due to extreme erosion. Unfortunately, it’s at imminent risk of falling into the sea unless it is moved back immediately.

You’ll find locally fashioned purple and white “wampum” jewelry sculpted from Quahog shells at Stony Creek Gifts right on the path to the overlook. These are authentic, but beware of the hawkers of “Indian Bead Necklaces” made in China.

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

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

Larsens Fish Market Menemsha MA
Larsens Fish Market

EAT: Larsens Fish Market – Menemsha

See above – Larsen’s always wins raves for its just pulled from the water seafood. And for its award-winning chowder. The ambience is fish-market rustic. Take your scrumptious eats to a patch of dock or grass or sand.

EAT/SCENE: Lookout Tavern – Oak Bluffs

This back-deck-like restaurant/bar 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.

Offshore Ale, Oak Bluffs: Marthas Vineyard MA

DRINK: Offshore Ale – Oak Bluffs

Grab a handful of peanuts in the shell, then sample a variety of house-brewed beer.

EAT: Atlantic Fish and Chop House – Edgartown

Right on the Edgartown docks, great seafood, basic and delicious, is enhanced by stunning harbor sunsets. Order the New England seaside version of Guacamole – with crabmeat – and you might just have to order a second one five minutes later.

EAT: Bettini at Harbor View Hotel – Edgartown

With French-Born Chef Patrice Martineau at the helm, Bettini has become a destination unto itself. Martineau honed his craft in his home country, NYC (Restaurant Daniel), and Montage in Beverly Hills before working his magic here. Cuisine is a “fresh take on Vineyard Style.” To that end, Chef sources everything from area farms, boats, and foragers for the freshest and most innovative dishes.

Marthas Vineyard Hotels

Harborview Hotel Marthas Vineyard MA
Harborview Hotel

STAY: 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.

Waterfront suite, Harbor View Hotel, Edgartown: Marthas Vineyard MA
Waterfront suite, Harbor View Hotel

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.

Charlotte Inn, Edgartown: Marthas Vineyard MA

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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  • Malerie Yolen-Cohen

    Malerie Yolen-Cohen is the Author of the cross-country travel guide, Stay On Route 6; Your Guide to All 3562 Miles of Transcontinental Route 6. She contributes frequently to Newsday, with credits in National Geographic Traveler, Ladies Home Journal, Yankee Magazine, Shape.com, Sierra Magazine, Porthole, Paddler, New England Boating, Huffington Post, and dozens of other publications. Malerie’s focus and specialty is Northeastern US, and she is constantly amazed by the caliber of restaurants and lodging in the unlikeliest places.

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2 thoughts on “A Couples’ Guide to Things to Do in Martha’s Vineyard”

  1. 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.

  2. MV is one of my favorite places – and has been since I was a kid. Thanks so much for reading and commenting! Malerie

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