Things to Do on Martha’s Vineyard: Top 23 Most Unique Spots

Just off the coast of Massachusetts, Martha’s Vineyard is a postcard destination. This island is a patchwork quilt of cultures, blending African American, Brazilian, Jamaican, and Native American threads. And that was before Ron DeSantis started sending migrants here, for some reason.

Think of iconic spots like the Aquinnah Cliffs and Chappaquiddick Island—they’re the heart of the island. And don’t miss the fairy-tale gingerbread cottages and the whimsical carousel in Oak Bluffs. Though only about 17,000 folks call it home year-round, summer sees nearly 200,000 visitors. The Vineyard is an ideal spot for a scenic beach getaway with a ton of things to do for all interests.

Ready to explore the best things to do on Martha’s Vineyard? Let’s get into it:

Quick hits

• • Rich History: Martha’s Vineyard is a time capsule. From its Native American roots to American history milestones, and even a cameo in ‘Jaws,’ it’s a treasure trove for history buffs and movie fans alike.

  • Summer Playground: Stroll past those charming gingerbread cottages, visit majestic lighthouses, lounge on beautiful beaches, or sail the Sound. On land, dive into shopping or savor local dining delights. Every corner of the island promises memories to cherish.

  • Warm Welcome: Martha’s Vineyard is all about hospitality. Plus, its closeness to Nantucket, Block Island, and Cape Cod makes it a great base for exploring New England’s stunning coastlines.

Map design by Stanton House Inn  with elements from Flaticon

 

A Brief History of Martha’s Vineyard

Martha’s Vineyard has a storied past. It began before written history from the Wampanoag inhabitants to the heyday of 19th-century whaling. This island, once the final home for the now-extinct heath hen, has had a front-row seat to American history, from the Revolutionary War to World War II.

The Early Days

Long before we had TikTok, the Wampanoag people called this island home. They were here way before Thomas Mayhew from Watertown, MA, bought the land in 1642. Mayhew was pretty chummy with the Wampanoags, setting up the first European settlement at Great Harbor, which we now call Edgartown. Mayhew’s buddy, Hiacoomes, converted to Christianity and spread the word.

In 1684, Rhode Island tried to muscle in with some militia, but let’s just say it didn’t go well for them. In 1825, Leavitt Thaxter, who married into the Mayhew clan, opened Thaxter Academy, welcoming both white and Native American kids.

The Whaling Boom

The 19th century was a whale of a time—literally. The island was a big deal in the whaling industry until kerosene came along and spoiled the party in the 1870s. But no worries, Martha’s Vineyard quickly became a summer hotspot instead. Even during the Great Depression, folks couldn’t stay away.

This place was also the last home for the heath hen, which sadly went extinct here in 1932. And during WWII, the island switched gears to military training ground from 1941 to 1945.

Modern Times

Linguist William Labov’s 1963 study on the island’s dialect was a game-changer in sociolinguistics. Then came the infamous “Chappaquiddick incident” in 1969, casting a shadow on what some see as a simpler time.

Did you know that in 1977 the island thought about seceding from Massachusetts? There’s even a flag for it. Skip ahead to December 2019, and you’ve got the Obamas making this their home base with a sprawling 30-acre estate.

But Martha’s Vineyard’s African American roots run deeper than the Obamas. Reverend Samuel Sewall was a local legend, speaking out against slavery way back when. The National Park Service even named the island an Underground Railroad site in October 2020.

Even with all its Hollywood fame from “Jaws,” Martha’s Vineyard stays true to its roots, charming visitors with its blend of culture, history, and sheer beauty.

Best Things to do on Martha’s Vineyard

Martha’s Vineyard, frequented by celebs like Oprah Winfrey and Michelle Obama, is your perfect New England summer getaway. The entire island is divided into six charming towns, each with its own flair:

• Aquinnah

• Chilmark

• Edgartown

• Oak Bluffs

• Tisbury

• West Tisbury

Locals have a quirky way of splitting the island into “Down Island” (Edgartown, Oak Bluffs, and Vineyard Haven) and “Up Island” (West Tisbury, Chilmark, and Aquinnah). Read on for the best spots!

Oak Bluffs

Oak Bluffs is a Victorian fairy tale. Start with the whimsical gingerbread cottages that look like they’re made of spun sugar. Take a self-guided walking tour through the Camp Meeting Association grounds and feel like you’ve stepped into a storybook. Don’t miss Ocean Park, where you can relax on lush lawns, enjoy the iconic gazebo, and breathe in that salty sea air at Oak Bluffs Harbor. Finish your afternoon over at Joseph Sylvia State Beach.

Enjoy Edgartown’s Charm

Edgartown is a blend of colonial architecture and maritime history. It’s perfect for beach lovers, shopaholics, and foodies alike. Stroll through picturesque streets with hydrangea gardens and historic homes. Visit the Edgartown Lighthouse and the Old Whaling Church, a stunning piece of Greek Revival architecture.

Explore Vineyard Haven

Vineyard Haven is quaint but lively, with a main street full of charming shops and cozy cafes. It’s less flashy than Oak Bluffs and Edgartown, but it has gems like Waterside Market, Magnetic North, and Bunch Of Grapes Bookstore. Perfect for a relaxing day out.

Bike along one side of the island

Grab a bike and pedal through the island’s scenic beauty. Cruise past Oak Bluffs’ busy streets, check out Edgartown’s historic lighthouses, and enjoy the coastal views. Biking here is the best way to soak in the island at your own pace.

Jump off Jaws Bridge or watch a screening

Take a leap off the iconic Jaws Bridge—those “No Jumping” signs are more about liability. If you’d rather stay dry, catch an outdoor screening of Spielberg’s classic and enjoy the nostalgia.

Aquinnah Cliffs

Don’t miss the majestic Aquinnah Cliffs, a stunning display of red, orange, and yellow clay. These clay cliffs overlooking Moshup Beach aren’t just a photographer’s dream—they tell the ancient story of the island’s formation. Fun fact: The town was once called Gay Head but decided to switch back to Aquinnah (thankfully).

Tour the Gay Head Lighthouse

The name persists at the historic Gay Head Lighthouse. This beacon’s been guiding sailors since 1796! You can take a guided formal tour or just wander around. Either way, you’ll see why this lighthouse is such a proud symbol of the island.

Enjoy the many different beaches on the island

Martha’s Vineyard is beach heaven, each with its own vibe. If you’re into surfing, South Beach in Edgartown is your spot. Norton Point Beach is one of the few places where you can drive right onto the sand—just don’t bring the beach back into your car!

For a quieter time, head to Menemsha. It’s perfect for evening picnics and sunsets. This little fishing village is also where the Coast Guard operates a rescue station. Added benefit is hitting-up a fish market after the beach. Here are some other must-see beaches:

• Lambert’s Cove: A secluded haven.

• State Beach: A family favorite.

• Katama Beach (South Beach): Three miles of sandy fun, with Atlantic waves on one side and a calm salt pond on the other.

• Moshup Beach: Framed by the colorful Aquinnah Cliffs, it’s a real showstopper.

Catch rings at the Flying Horse Carousel

Take a ride on the Flying Horses Carousel, the oldest platform carousel in the U.S. It’s a nostalgic return to childhood. Try to grab the brass ring for a chance to win a free ride—and another dose of fun.

Stroll the walking trails

Explore Martha’s Vineyard on foot! Wander the wooded paths of Felix Neck Wildlife Sanctuary or take in the coastal views at Caroline Tuthill Preserve. Each trail offers a peaceful escape into the island’s natural beauty.

Sail in the Vineyard Sound

Set sail on Vineyard Sound and let the sea breeze carry you away. With the beautiful coastline as your backdrop, sailing here is pure magic.

Go golfing on a public course

Hit the links at one of Martha’s Vineyard’s public golf courses:

• Mink Meadows Golf Club

• Farm Neck Golf Club

• Royal and Ancient Chappaquiddick Links

Visit Chappaquiddick Island

Hop on a ferry from Edgartown to Chappaquiddick Island, or “Chappy” as the locals call it. This peaceful spot has unspoiled beaches, nature trails, and the historic Cape Poge Lighthouse. And per a certain Kennedy, steer clear of the bridge—just saying!

Visit the Island Alpaca Farm

For something different, check out the Island Alpaca Farm. You’ll meet the adorable alpacas and learn all about them. It’s a fun break from the beach and a hit with kids and adults alike.

Visit at least one of the Lighthouses

If you’re hitting up Martha’s Vineyard, you’ve got to check out at least one of its iconic lighthouses. Here are a couple of must-sees:

• Edgartown Lighthouse: Full of stories and right in the heart of things.

• Cape Poge Lighthouse: A bit more off the beaten path, but worth the trip.

These lighthouses are like the island’s guardians, giving you a peek into its maritime history and offering some pretty breathtaking views.

Learn The Local History At The Martha’s Vineyard Museum

Discover the island’s past at the Martha’s Vineyard Museum. You can:

• Explore fascinating exhibits and artifacts.

• Learn about the island’s diverse origins, from Native American heritage to maritime adventures.

It’s a great spot to soak up some history and get a real feel for what makes this place tick.

Things to do on Martha’s Vineyard at night: Enjoy the nightlife and enjoy a sunset or two

When the sun sets, Martha’s Vineyard comes alive! Here’s a little nightlife guide:

• Music and Bars: Feel the legacy of James Taylor and Carly Simon with live folk music. Head to The Ritz, a dive bar where local bands keep the energy high.

• Red Cat Kitchen: Catch acts like Johnny Hoy and the Bluefish for some fantastic tunes.

• Ben & Bill’s Chocolate Emporium: Indulge in some classic ice cream flavors for a sweet trip down memory lane.

• Other Hot Spots: Check out The Cardboard Box, The Sand Bar & Grille, and The Newes from America for a mix of lively entertainment and relaxed vibes.

Shopping on Martha’s Vineyard

Ready to shop? Martha’s Vineyard is a shopper’s paradise with a little something for everyone:

• Edgartown: Wander through boutiques with local crafts, designer goods, art galleries, candy stores, home decor shops, and clothing stores for all. Don’t miss the bookstores and unique souvenirs.

• Vineyard Haven: Stroll down the charming main street filled with eclectic shops and cozy restaurants. The nearby West Chop Lighthouse adds to the scenic experience.

• Morning Glory Farm: In Edgartown, this farm stand is a gem for fresh produce, delicious baked goods, and premade meals—perfect for food lovers.

• Original Vineyard Vines Store: Also in Edgartown, this is the go-to spot for upscale clothing and accessories to nail that classic New England look. They even offer styling appointments!

Annual Events on Martha’s Vineyard

Martha’s Vineyard is a year-round party, packed with events that’ll make you fall in love with the island even more. Here are some of the highlights:

• Big Chili Contest (May): Held at the PA Club in Oak Bluffs, this spicy event supports local non-profits and attracts chili lovers from all over. Get ready to taste some fiery creations!

• MV Wine Festival: A weekend filled with good food, good wine, and great company. Cheers to that!

• Independence Day: Classic Americana at its best with hot dogs, burgers, antique cars, and fun floats. Grab a spot at Vineyard Square for the parade and fireworks.

• Illumination Night: This century-old tradition lights up the night with beautiful Chinese and Japanese lanterns and a community sing-along. Pure magic!

• Martha’s Vineyard Agricultural Society Fair (August): Starting the third Thursday of August, this fair is all about animal shows, crafts, and friendly competitions. Plus, the Oak Bluffs Fireworks on the third Friday is a summer highlight.

• Vineyard Artisans Festival (Columbus Day weekend): A free event where local crafters show off their masterpieces at Grange Hall in West Tisbury. There’s fun for kids and delicious food and drink vendors.

• Edgartown Christmas Celebration: When winter rolls in, Edgartown turns into a festive wonderland with sparkling decorations, carriage rides, and Santa waiting for photo ops. The special shopping events make holiday magic come to life.

Restaurants in Martha’s Vineyard

Alright, foodies, let’s talk about the amazing eats on Martha’s Vineyard. This place is a culinary paradise!

• Seafood: Head to Menemsha fishing village for the freshest seafood. Larsen’s Fish Market is a favorite, serving up cooked-to-order lobster, chowders, steamers, and mussels. Picture a lobster roll so fresh, it’s like the ocean’s greeting.

• Sweet Treats: Mad Martha’s ice cream parlor is a local treasure with homemade flavors that are pure indulgence. And for night owls and early risers, Back Door Donuts offers irresistible pastries. Their maple bacon donut? A must-try.

• Chocolate: Murdick’s Fudge is a haven for chocolate lovers, offering a rich assortment of flavors that’ll satisfy any sweet tooth.

• Craft Beer: Beer aficionados will love Offshore Ale Company. Their variety of IPAs paired with a fresh lobster roll is the quintessential Vineyard experience.

Directions to Martha’s Vineyard from Greenwich, CT

Ready to head to Martha’s Vineyard from our New England bed and breakfast in Greenwich, CT? It’s a breeze whether you go by sea or air.

By Ferry

You can catch ferries from:

• Woods Hole, MA, part of Falmouth, MA, on Cape Cod

• New Bedford, MA

• North Kingstown, RI

Book your car’s passage early for the summer—it fills up faster than a beach on a hot day! Traveling without a car? No worries, passenger tickets make for an easy trip. Choose from:

• Hyline Cruises

• Island Queen

• Steamship Authority

For a quicker ride, the Edgartown Fast Ferry zips you straight to Edgartown. SeaStreak Ferries and Inter-island options offer more routes for the sea-loving adventurer.

By Air

Flying is a popular option, especially if you don’t have a private jet. Direct flights from airports near Greenwich, CT, are available with:

• Cape Air

• Delta

• American Airlines

• JetBlue

Enjoy the bird’s-eye view of the ocean and the Vineyard as you fly in.

Hotels, Inns, and Places to Stay in Martha’s Vineyard

Martha’s Vineyard is not just any old destination. It’s a lifestyle, with accommodations for every taste and budget.

First time visiting? Stay in Edgartown, MA. Stay in Edgartown, MA. You’ll love the pristine beaches, fine dining, and pretending you’re a lighthouse keeper at Edgartown Lighthouse.

As far as unique places to stay there and nearby, there’s:

• Winnetu Resort: Stunning rooms, on-site dining, relaxing massages, a pool, and a kid’s club at this New England resort.

• The Harborside Inn: Historic charm meets modern luxury, with a pool offering splendid harbor views.

• Summercamp in Oak Bluffs: Nostalgic vibes, revamped in 2016 for a whimsical stay at the base of the Methodist campground.

• Nobnocket Boutique Inn: Modern design, nestled within 2 acres of serene woodland and gardens in Vineyard Haven.

More Nearby Cities and Towns to Explore Near Martha’s Vineyard

Once you’ve soaked up Martha’s Vineyard, why not explore nearby gems? Each are major Northeast weekend getaways in their own right. And each of these East Coast road trip destinations host their own unique charm, like different flavors of New England clam chowder—distinct, memorable, and irresistible.

Elizabeth Islands

A quiet haven with a laid-back vibe among its island residents. Perfect for slowing down and enjoying the Atlantic’s splendor of the summer season.

Nantucket

A short ferry ride away, Nantucket’s cobblestone streets and whaling history are enchanting. Enjoy harbor views at CRU or sip craft brews at Cisco Brewers.

Block Island

Dramatic cliffs and serene beaches make Block Island a tranquil escape. Hang a “gone fishin’” sign and relax by the sea.

Cape Cod

Just a hop from Martha’s Vineyard, Cape Cod is a New England getaway at its best. Iconic lighthouses, a pristine national seashore, and quaint New England villages await.

Tl;dr

When your tour of Martha’s Vineyard wraps up, you’ll pocket memories as sweet as the island’s fudge. You’ll think back on:

• Fairy-tale gingerbread cottages

• Majestic lighthouse views

• Sunsets that dazzle like a grand finale

Martha’s Vineyard mixes history with fun, inviting travelers to uncover its hidden treasures. Whether you’re strolling through vibrant harbors or relaxing on tranquil beaches, this island offers an enchanting escape for everyone.

Frequently Asked Questions

Can I walk around Martha’s Vineyard?

Oh, absolutely! Walking around Martha’s Vineyard is the best way to soak up its charm. In the main port towns like Vineyard Haven, Oak Bluffs, and Edgartown, you can explore every nook on foot. If you want, you can also hop on a bike or catch the public bus. Skip the scooters and cars; walking is the secret ingredient for a perfect day. So tie those laces tight and let your curiosity guide you!

How much time should you spend on Martha’s Vineyard?

Plan to spend at least two days to get a good feel for the island and its offerings. If you find yourself wanting more, there’s plenty to keep you busy for a longer stay.

What is the best time of year to visit Martha’s Vineyard?

The best time to visit is during the summer for warm weather, beautiful beaches, and a full schedule of activities. However, a New England spring or New England fall getaway are a quieter, more relaxed experience with cooler temperatures. Enjoy your trip!

Are there any activities for children on Martha’s Vineyard?

Without a doubt, Martha’s Vineyard is a kid’s wonderland. Little ones can ride the vintage Flying Horse Carousel, make furry friends at the Island Alpaca Farm, and build majestic sandcastles on welcoming beaches. It’s an island where imagination reigns supreme for young adventurers.

Do I need to bring a car to Martha’s Vineyard?

No need to bring a car, or car rentals! The island has a good public bus system and is easily accessible by bike or on foot. Enjoy your visit!

 

Updated and republished: July 30, 2024