Things To Do On Martha's Vineyard: Top 23 Most Unique Spots | Stanton House Inn
A sailboat sails past a green island off the coast of Martha's Vineyard.

Just off the coast of Massachusetts, Martha’s Vineyard is as idyllic a summer retreat as they say. The island bursts with a surprising amount of cultural diversity. The island’s tapestry weaves together:

  • African American

  • Brazilian

  • Jamaican

  • And Native American threads

And that was before Ron DeSantis started sending migrants here, for some reason.

Landmarks such as the Aquinnah Cliffs and Chappaquiddick Island are uniquely Martha’s Vineyard. And the whimsical gingerbread cottages and the carousel in Oak Bluffs add a touch of enchantment. Though home to about 17,000 year-round, the population swells to nearly 200,000 during the summer months. 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

  • Martha’s Vineyard is steeped in history. It’s unique quirks stretch from Native American origins to pivotal American conflicts, even a surprise role in the ‘Jaws’ movie. It’s an island that’s sure to captivate any history enthusiast or shark aficionado.

  • The island is a summer playground. Wander past charming gingerbread cottages, visit the lighthouses, relax on the beaches, or sail the Sound. Or stay on land and indulge in shopping or dining. Each experience ensures a visit filled with lasting memories.

  • Martha’s Vineyard welcomes visitors with open arms. Its proximity to Nantucket, Block Island, and Cape Cod also makes it a prime point for exploring more of New England’s coastal regions.

  things to do on marthas vineyard map Things to Do on Martha's Vineyard: Top 23 Most Unique Spots Map design by Stanton House Inn  with elements from Flaticon

 

A Brief History of Martha’s Vineyard

1902 image of summer cottages on 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.

Colonial Era

The island’s tale begins in 1642 when Thomas Mayhew of Watertown, MA, purchased the land from the Wampanoag people. His amicable relations with the Wampanoags led to the establishment of the first European settlement at Great Harbor. It’s now known as Edgartown. Mayhew’s alliance with the Wampanoag Hiacoomes resulted in the latter’s embracing Christianity. Years later, in 1665, Mayhew’s lands became part of a grant to the Duke of York, and settlers began to arrive in 1671.

An attempt to claim Martha’s Vineyard was made in 1684 by Rhode Island with a band of militia. This effort failed spectacularly.

Hon. Leavitt Thaxter, who married into the Mayhew family, was a respected educator in Edgartown and a staunch ally of the Native Americans. He founded Thaxter Academy in 1825, which was notable for educating both white and Native American youth.

Industrial Era

1910 photo of the Railroad at Katawa Lodge

Martha’s Vineyard rose to fame in the 19th century with its whaling industry. When kerosene replaced whale oil, the industry collapsed by 1870. Luckily, the island reinvented itself as a coveted vacation spot.

Even with the downturn of the Great Depression, Martha’s Vineyard’s allure as a tourist destination only grew stronger. It also served as the last sanctuary for the heath hen, which went extinct here in 1932. During World War II, the island shifted from leisure to military readiness. The Vineyard hosted training exercises for the Army, Navy, and Air Force from 1941 to 1945.

Modern Era

Linguist William Labov’s 1963 study on the island’s dialect became a landmark in sociolinguistics. The year 1969 brought notoriety with the “Chappaquiddick incident,” which cast a shadow over a bridge meant for simpler times. In 1977, the island contemplated secession from Massachusetts. You can still see the flag designed for the movement across the island.

In December 2019, President Barack Obama chose the Vineyard for his family’s 30-acre homestead. The island’s African American heritage was significant before that, though. Local figures like Reverend Samuel Sewall advocated against slavery here, for example. The National Park Service recognized the island as an Underground Railroad Site in October 2020.

Even with its brush with Hollywood during the filming of “Jaws”, Martha’s Vineyard remains grounded in its rich history. It continues to enchant visitors and residents with its unique blend of culture, history, and scenic beauty.

Best Things to do on Martha’s Vineyard

Exploring the colorful Gingerbread cottages in Oak Bluffs

Frequented by celebrities like Oprah Winfrey and Michelle Obama, six towns compose the island, each unique:

  • Aquinnah

  • Chilmark

  • Edgartown

  • Oak Bluffs

  • Tisbury

  • And West Tisbury

The locals divide the entire island according to its directional distinctions:

  • “Down island” includes the vibrant communities of Edgartown, Oak Bluffs, and Vineyard Haven.

  • “Up island” features the tranquil West Tisbury, Chilmark, and Aquinnah.

Martha’s Vineyard is the perfect New England summer getaway, especially for celebrating the Fourth of July. Here, you can enjoy the simple pleasures of barefoot walks and stunning sunsets that outshine the brightest fireworks.

Oak Bluffs

Tranquil Ocean Park with scenic views and the cottage city, a postcard picture of island life

Oak Bluffs is a delightful destination. Start a visit with the whimsical gingerbread cottages that seem plucked from a Victorian fairy tale. Built on Methodist camp meeting grounds, these cottages feature intricate trimmings reminiscent of spun sugar. Take a self-guided walking tour through the Camp Meeting Association grounds. It’ll feel like stepping into a storybook. The nearby Ocean Park offers a tranquil respite with its lush lawns and iconic gazebo. Enjoy leisurely strolls, soak in the scenic beauty, and breathe in the salt-tinged air from Oak Bluffs Harbor. The park provides panoramic views and is close to the calm shores of Joseph Sylvia State Beach.

Enjoy Edgartown’s Charm

Colonial architecture and maritime heritage merge at Edgartown. Plus, access to beaches, shops, restaurants, and the Edgartown lighthouse. The downtown area is picturesque with its hydrangea gardens, historic homes, and charming streets. The Old Whaling Church is a testament to the town’s whaling history, with its Greek Revival and Federal-style architecture.

Explore Vineyard Haven

Vineyard Haven is a quaint town with a lively main street and scenic harbor. It’s a cute spot of charming shops, cozy cafes, and a tranquil waterfront. While the town has fewer big attractions compared to Oak Bluffs and Edgartown. That said, it still boasts must-visit spots such as Waterside Market, Magnetic North, and Bunch Of Grapes Bookstore.

Bike along one side of the island

Embark on a cycling journey through Martha’s Vineyard and soak in the island’s coastal charm. Bike past the bustling streets of Oak Bluffs and the historic lighthouses of Edgartown. Biking here is an invitation to enjoy the island’s natural splendor at your own pace.

Jump off Jaws Bridge or watch a screening

For those seeking a thrill, take a leap from the iconic Jaws Bridge into the waters of Vineyard history. While signs say no jumping, it’s more of a liability thing. This legendary bridge is a gateway to the island’s pop culture legacy. Or avoid getting wet and relive Spielberg’s classic with a local outdoor screening.

Aquinnah Cliffs

Breathtaking view of Aquinnah Cliffs and lighthouse, looking towards the Atlantic Ocean

The majestic Aquinnah Cliffs rise from the island’s shoreline. They present a stunning display of natural artistry. With hues of red, orange, and yellow clay, these clay cliffs are not only a photographer’s dream but also a geological wonder. They tell the ancient story of Martha’s Vineyard’s formation. The town once decided to be called Gay Head, but changed it back (thankfully).

Tour the Gay Head Lighthouse

The name persists at the historic Gay Head Lighthouse. This has been a beacon of maritime navigation since 1796. Choose between a guided tour or explore on your own, and discover why this lighthouse is a proud symbol of the island’s rich history.

Enjoy the many different beaches on the island

Sign to Oak Bluffs State Beach

Martha’s Vineyard has a trove of beaches, each with its own distinct vibe. For the surf enthusiast, South Beach in Edgartown is the prime spot for catching waves and riding the ocean’s rhythm. Norton Point Beach stands out as one of two beaches where cars are welcome on the sand. But remember, no beachside parking means no sandy car interiors!

Prefer something a little more quiet? Menemsha’s shores or Moshup Beach offer a peaceful retreat, ideal for evening picnics as the sun dips below the horizon. The island’s coastal lineup is diverse:

  • Lambert’s Cove provides a secluded haven

  • Joseph Sylvia State Beach is a family favorite

Katama Beach, also known as South Beach, stretches three miles,. This sandy expanse butts up against the Atlantic’s might, while its calm salt pond caters to those seeking gentle waters. Moshup Beach, a picturesque spot framed by the colorful Aquinnah Cliffs, is a visual masterpiece and a beachgoer’s dream.

Catch rings at the Flying Horse Carousel

Take a nostalgic ride on the nation’s oldest platform carousel, the Flying Horses Carousel, and let the joy of childhood whimsy wash over you. As you reach for the brass ring, each turn brings a chance to win another go-round, and with it, another cherished memory on this historic island.

Stroll the walking trails

Walking path

Wander Martha’s Vineyard’s walking trails and embrace the island’s tranquil beauty. Find solace in the wooded paths of Felix Neck Wildlife Sanctuary or the coastal vistas of Caroline Tuthill Preserve. Each trail offers a peaceful escape into the island’s diverse landscapes.

Sail in the Vineyard Sound

Let the gentle sea breeze guide you on a maritime adventure as you set sail on the tranquil waters of Vineyard Sound. With the coastline as your backdrop, sailing in Martha’s Vineyard is an idyllic way to experience the island’s seafaring soul.

Go golfing on a public course

Enjoy a leisurely round of golf on Martha’s Vineyard’s public courses:

Whether you’re an experienced golfer or just playing for fun, the island’s scenic greens provide a beautiful backdrop for a day on the links.

Visit Chappaquiddick Island

Chappaquiddick ferry

Discover the tranquil allure of Chappaquiddick Island. This peaceful haven features:

  • Unspoiled beaches

  • Meandering nature trails

  • The storied Cape Poge Lighthouse

A brief ferry journey from Edgartown transports you to “Chappy,” as the locals affectionately call it.

A certain Kennedy would hopefully warn you to avoid the bridge.

Visit the Island Alpaca Farm

At the Island Alpaca Farm, educational tours introduce you to the farm’s gentle residents. This working farm provides a delightful diversion from the island’s beach-centric activities.

Visit at least one of the Lighthouses

Scenic view of Edgartown Lighthouse against the coastal backdrop

A trip to Martha’s Vineyard would be incomplete without visiting at least one of its iconic lighthouses. Whether you choose:

  • The storied Edgartown Lighthouse

  • Or the secluded Cape Poge Lighthouse

These coastal guardians provide a window into the island’s maritime past and offer some of the most exquisite views imaginable.

Learn The Local History At The Martha’s Vineyard Museum

At the Martha’s Vineyard Museum, you can:

  • Delve into the rich tapestry of the island’s history

  • Explore fascinating exhibits and artifacts

  • Learn about the Vineyard’s diverse origins, from its Native American heritage to its maritime exploits and beyond

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

Beachgoers enjoying the summer on a Vineyard beach

Martha’s Vineyard is a beacon for night owls. The nightlife rivals the island’s own sunsets for sheer brilliance.

Folk music echoes the legacy of James Taylor and Carly Simon, with live performances filling the summer air every evening. The Ritz, a dive bar with year-round appeal, inspires patrons to tap their feet to the rhythm of local bands.

Red Cat Kitchen hosts acts such as Johnny Hoy and the Bluefish, ensuring the island’s beats are delectable. For a taste of nostalgia, Ben & Bill’s Chocolate Emporium serves up classic ice cream flavors that whisk you back to simpler times. Events across the island, from:

  • The Cardboard Box

  • To The Sand Bar & Grille

  • And The Newes from America

Offer a mix of lively entertainment and laid-back vibes. Whether you’re in the mood to dance or relax, Martha’s Vineyard’s nightlife has the perfect setting.

Shopping on Martha’s Vineyard

Murdik's Fudge sign

Martha’s Vineyard is a shopper’s paradise, offering a delightful mix of retail experiences.

In the charming boutiques of Edgartown, you’ll find local crafts that tell tales of the sea, alongside designer wares that catch the eye. The town is a treasure trove with art galleries, candy stores, home decor shops, and clothing stores for both women and men. Don’t forget to pop into a bookstore or pick up a unique island souvenir to capture the memories.

Over in Vineyard Haven, the main street exudes charm, lined with eclectic shops and cozy restaurants that feel like a beacon in the night. The West Chop Lighthouse adds to the scenic shopping experience with its stunning ocean views.

Morning Glory Farm in Edgartown is a must-visit for fresh produce, delicious baked goods, and convenient premade meals. This farm stand is a delightful stop for food lovers.

For a touch of coastal style, the Original Vineyard Vines Store in Edgartown is the place to be. They offer upscale clothing and accessories, perfect for achieving that New England look. They even provide styling appointments to ensure your outfits are as perfect as a Vineyard getaway.

Annual Events on Martha’s Vineyard

The historic district of Oak Bluffs

Martha’s Vineyard shines all year with events that capture the island’s festive spirit:

  • The annual Big Chili Contest, held in May at the PA Club in Oak Bluffs, benefits local non-profits. It attracts entrants and chili fans from around the world.

  • The annual MV Wine Festival offers a weekend of good food, good wine, and plenty of good people.

  • Independence Day is a celebration of old-school Americana, featuring hot dogs, burgers, antique cars, and fun floats. Vineyard Square is the best spot to see the parade and to stake out a spot for the fireworks.

  • Illumination Night is a Vineyard tradition that began over a century ago. It’s a community sing-along as darkness falls, with lighting of beautiful Chinese and Japanese lanterns.

  • The annual Martha’s Vineyard Agricultural Society Fair starts on the third Thursday of August. It features animal shows, crafts, and competitions. The Oak Bluffs Fireworks is held on the third Friday of August. It’s a major celebration of summer on Martha’s Vineyard. The festival features workshops, tastings, wine dinners, and the Grand Tasting. It’s a must-do event for food enthusiasts.

  • The Vineyard Artisans Festival is a highlight of Columbus Day weekend. This free celebration is where crafters unveil their masterpieces. Children’s laughter fills the air at the playground, while food and drink vendors offer a bounty fit for a king at Grange Hall in West Tisbury.

  • And when winter whispers through the streets, the Edgartown Christmas Celebration lights up the town. Decorations sparkle on every corner, festive activities abound, and carriage rides offer a quaint throwback to yesteryear. Santa awaits to create lasting memories with photos, and special shopping events evoke the magic of the holiday season.

Restaurants in Martha’s Vineyard

Fresh fish and chips and a giant lobster roll overlooking the ocean at Lake Bluff on Martha's Vineyard.

Martha’s Vineyard is a culinary paradise, offering a diverse array of dining experiences. Seafood enthusiasts will revel in the waterfront shacks, where the day’s catch goes straight from the docks to the dish. Picture a lobster roll so fresh, it’s like the ocean’s greeting. Head to Menemsha fishing village for the freshest. Larsen’s Fish Market is a favorite, serving cooked to order lobster, chowders, steamers, and mussels. For a sweet treat, Mad Martha’s ice cream parlor is a local treasure, serving up homemade flavors that are pure indulgence.

Night owls and early risers alike will appreciate Back Door Donuts. The pastries, ranging from classic glazed to inventive maple bacon, are irresistible at any hour. Chocolate lovers won’t want to miss Murdick’s Fudge, with its rich assortment of flavors, each a piece of chocolate heaven.

Beer aficionados can sample the craft brews at Offshore Ale Company, where the variety of IPAs complements a full food menu. A lobster roll paired with a fresh ale encapsulates the quintessential Vineyard experience.

Directions to Martha’s Vineyard from Greenwich, CT

Martha’s Vineyard, that enchanting island retreat, could be a stone’s throw from our New England bed and breakfast in Greenwich, CT. Accessible by both air and sea, you can embark on a maritime journey via ferries from:

  • Cape Cod

  • New Bedford, MA

  • Or North Kingstown in Rhode Island

Remember to book your car’s passage early for the summer season, as spots fill up faster than a beach on a hot day! For those traveling without vehicles, passenger tickets are available for a breezy commute.

Choose from a fleet of ferry services including:

  • Hyline Cruises

  • Island Queen

  • And the Steamship Authority

For a more direct route, the Edgartown Fast Ferry offers swift access straight to the heart of Edgartown. SeaStreak Ferries and the Inter-island options provide extra routes for the intrepid sea traveler.

Or fly here, like most Greenwich residents. Don’t own your own private jet? Direct flights are available from airports near Greenwich, CT, via major carriers:

Cape Air

Delta

American Airlines

And Jet Blue

These flights offer a bird’s-eye view of the ocean’s expanse, as well as the Vineyard.

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

Summercamp at sunset

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. Here, you can soak up the sun on pristine beaches, enjoy fine dining downtown, and play pretend as a lighthouse keeper at Edgartown Lighthouse.

There’s:

  • Winnetu Resort, offering stunning rooms, on-site dining, relaxing massage services, a welcoming pool, and a kid’s club.

  • The Harborside Inn combines historic charm with modern luxury, featuring a pool with splendid harbor views.

  • Summercamp in Oak Bluffs brings a touch of nostalgia, revamped in 2016 to offer a whimsical stay at the base of the Methodist campground.

  • For a more contemporary retreat, the Nobnocket Boutique Inn boasts seven rooms of modern design. And all nestled within 2 acres of serene woodland and gardens in Vineyard Haven.

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

Boats in the harbor of a fishing village

Ready for a coastal adventure beyond Martha’s Vineyard? Then plan a visit to the nearby cities and towns. Each is major Northeast weekend getaways in their own right. And each East Coast destinations offers a unique experience. Like savoring the varied flavors of a New England clam chowder—distinct, memorable, and irresistible.

Elizabeth Islands

The Elizabeth Islands offer a quiet haven. Their low-key atmosphere is a balm for those weary of the fast pace. Here, surrounded by the Atlantic’s splendor, life for island residents moves to a leisurely, soothing rhythm.

Nantucket

Salt marshes protect the calm waters of Nantucket harbor

Nantucket is a world unto itself. Your footsteps on cobblestone streets echo with whaling history. And its beaches invite tranquility. Just a short ferry ride from Martha’s Vineyard, it offers a serene complement to your island adventure. Dine at CRU with views of the harbor, or sample craft brews at Cisco Brewers for a taste of Nantucket’s unique charm.

Block Island

South East Lighthouse at Block Island

Block Island and the Elizabeth Islands are where tranquility reigns, and the landscape’s drama is captivating. Dramatic cliffs tower over serene beaches, while protected wildlife thrives.

Block Island invites you to hang a “gone fishin'” sign, encouraging relaxation by the sea or with a book in hand. It’s a place for disconnecting from life’s buzz and savoring nature’s symphony.

Cape Cod

A beaten path through the fragile ecosystem on Cape Cod

From Martha’s Vineyard, a short journey brings you to the shores of Cape Cod, the epitome of New England splendor. Iconic lighthouses, a pristine national seashore, and quaint villages await. Cape Cod enriches any trip with its storied history, vibrant culture, and a wealth of seaside activities.

Tl;dr

After you tour of Martha’s Vineyard ends, pocket memories as sweet as the island’s fudge. You’ll reminisce about:

  • Fairy-tale gingerbread cottages

  • Majestic lighthouse views

  • And sunsets that dazzle like a grand finale

This island blends history with festivity, beckoning travelers to explore its hidden treasures. Whether strolling through vibrant harbors or relaxing on tranquil beaches, Martha’s Vineyard offers an enchanting retreat for all who visit.

Frequently Asked Questions

Can I walk around Martha’s Vineyard?

Oh, absolutely! Strolling through Martha’s Vineyard is the quintessential way to experience the island’s charm. In the main port towns like Vineyard Haven, Oak Bluffs, and Edgartown, you can explore every nook on foot. If you prefer, hop on a bike or catch the public transport. 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?

You should spend at least two days on Martha’s Vineyard to get a good feel for the island and its offerings. If you find yourself wanting more, Vineyard Square can help you plan a longer itinerary.

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

The best time to visit Martha’s Vineyard is during the summer for warm weather, beautiful beaches, and a full schedule of activities. However, spring and fall offer 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 child’s wonderland. Kids can ride the vintage Flying Horse Carousel, make furry friends at the Island Alpaca Farm, and construct majestic sandcastles on welcoming beaches. It’s an island where imagination reigns supreme for the young adventurers.

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

Bringing a car to Martha’s Vineyard is not necessary. The island has a good public bus system and is easily accessible by bike or on foot. Enjoy your visit!

 

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