12 Bucket-List Things to Do in Martha’s Vineyard (Local Favorites)

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I still remember stepping off the ferry in Vineyard Haven for the first time…salt in the air, pastel houses lining the harbor, everything slower in the best possible way. Since then, Martha’s Vineyard has become one of those places I keep returning to, not just for the beaches or the seafood, but for that feeling of timeless escape. As a Bostonian, it’s an easy place to get to, yet it truly feels world’s apart!

There’s more to this island than meets the eye. Sure, the gingerbread cottages in Oak Bluffs and the cliffs at Aquinnah are iconic, but it’s the quieter moments that stick with me: biking past stone walls in Chilmark, sipping local wine in Edgartown, watching a sunset from Menemsha Beach with a lobster roll in hand. And if you’ve never jumped off the Jaws Bridge… well, that’s basically a rite of passage. Here are 12 fun things to do in Martha’s Vineyard that feel as classic and magical as the island itself.

Fun Things to Do in Martha’s Vineyard

Planning a trip to Martha’s Vineyard? Here’s a quick-hit list of the island’s most iconic, scenic, and soul-soothing experiences. If you’re craving cliffs, cottages, or coastal bike rides, this will help you map it all out. Tap any spot below to jump to its section in the guide.

• Most Jaw-Dropping View: Aquinnah Cliffs
• Best Way to Explore the Island: Scenic Bike Trails
• Top Sunset Spot: Menemsha Beach
• Coolest On-the-Water Experience: Sailing Adventures
• Best Craft Beer Hangout: Bad Martha Farmer’s Brewery
• Top Hidden Beach: Lobsterville Beach
• Most Peaceful Garden Stroll: Polly Hill Arboretum
• Best Small-Town Charm: Vineyard Haven
• Most Creative Vibe: Oak Bluffs Arts District
• Most Unexpected Animal Encounter: Island Alpaca
• Best Farm-to-Table Foodie Fix: Farm-to-Table Dining at The Grey Barn
• Quintessential Lighthouse Moment: Edgartown Lighthouse Beach

Here’s how I recommend doing it: rent a bike in Vineyard Haven, cruise to Oak Bluffs for art and gingerbread cottages, detour to the cliffs in Aquinnah, then end your day with seafood and sunset in Menemsha. There’s a magic to this island…keep reading for all the details.

1. Aquinnah Cliffs

The Aquinnah Cliffs are one of Martha’s Vineyard’s most striking natural landmarks. These multi-colored clay cliffs, shaped by thousands of years of erosion, offer breathtaking panoramic views of the Atlantic Ocean. Located on the western tip of the island, this area is also home to the Wampanoag Tribe of Gay Head, adding cultural significance to the site. A short walk leads to an observation deck where you can admire the dramatic landscape and spot the historic Gay Head Lighthouse, which has stood as a coastal guardian since 1856.

During my visit, the sunset transformed the cliffs into a glowing masterpiece of red, orange, and gold—an unforgettable sight. While climbing the cliffs is prohibited, you can explore nearby Moshup Beach, known for its smooth stones and crashing waves. Before leaving, stop by the local shops for Wampanoag crafts and seafood at Aquinnah Shop Restaurant, which has the island’s best waterfront views.

2. Scenic Bike Trails

Exploring Martha’s Vineyard by bike is an adventure that blends exercise with stunning scenery. The island offers well-maintained trails that connect charming towns, scenic coastlines, and historic landmarks. One of the best routes is the Beach Road Path, which stretches from Oak Bluffs to Edgartown, offering views of the ocean and the iconic Jaws Bridge. Another popular option is the State Forest Loop, a peaceful ride through shaded woodlands and open meadows.

I rented a bike in Vineyard Haven and cycled past lighthouses, beaches, and colorful cottages. The best part? The freedom to stop anywhere…whether it’s for fresh seafood in Menemsha or a quick dip at South Beach. With bike-friendly roads, rental shops, and scenic picnic spots along the way, cycling is one of the best ways to experience Martha’s Vineyard’s natural beauty at your own pace. For me, it’s easily one of the prettiest parts of the Cape.

3. Menemsha Beach

If you’re looking for the best sunset on Martha’s Vineyard, head to Menemsha Beach. Located in the fishing village of Menemsha, this peaceful spot is famous for its unobstructed sunset views over the Vineyard Sound. Unlike the busier beaches, Menemsha has a quiet, laid-back feel, perfect for unwinding by the water. Bring a blanket, grab a lobster roll from Larsen’s Fish Market, and watch the sky explode into shades of pink and orange.

During my visit, I watched local fishermen bring in their daily catch while families gathered for an evening picnic. The lack of big crowds made the experience even better. While there are no waves for surfing, the calm waters are great for swimming. Arrive early to secure parking, and don’t forget your camera—the sunset here is one of the most breathtaking sights on the island.

4. Sailing Adventures

Sailing around Martha’s Vineyard is an unforgettable experience, whether you’re an expert or stepping onto a boat for the first time. Edgartown Harbor is the best place to start, with plenty of charters offering private and group excursions. From leisurely sunset cruises to hands-on sailing lessons, there’s an option for everyone. You’ll pass by iconic sights like Chappaquiddick Island, the Edgartown Lighthouse, and possibly even spot dolphins playing in the waves.

I joined a sunset sail, and nothing compares to the feeling of gliding across the water with the salty breeze in your hair. The island’s coastline looks even more stunning from the sea, and the golden hour lighting is perfect for photos. If you’re up for an adventure, some charters even let you help hoist the sails. Sailing is one of the most exciting ways to experience the island’s maritime history and natural beauty.

5. Bad Martha Farmer’s Brewery

For a laid-back afternoon with great drinks, Bad Martha Farmer’s Brewery in Edgartown is the perfect spot. This local craft brewery offers a variety of island-inspired beers, from the crisp Martha’s Vineyard Ale to the refreshing Honey Helles Lager, brewed with island honey. The brewery’s rustic barn setting, surrounded by gardens, adds to the relaxed atmosphere, making it an ideal place to unwind after a day of exploring.

During my visit, I enjoyed a flight of seasonal brews while lounging in the beer garden. They also serve light bites like cheese plates and warm pretzels, pairing perfectly with the beer. The best part? A portion of their profits goes to local charities, so you can sip with a purpose. Whether you’re a beer enthusiast or just looking for a fun, casual hangout, this brewery is a must-do rainy day activity in Cape Cod.

6. Lobsterville Beach

If you’re searching for a peaceful beach away from the crowds, Lobsterville Beach in Aquinnah is a hidden gem. This quiet, two-mile stretch of sand is perfect for fishing, birdwatching, or simply soaking up the sun. The calm, shallow waters make it ideal for wading and paddleboarding, while the lack of big waves keeps it family-friendly. It’s also one of the best shore fishing spots on the island, with striped bass and bluefish frequently caught here.

I spent an afternoon here, enjoying the solitude and watching ospreys dive for fish. Unlike more popular beaches, there are no snack bars or large parking lots, so bring your own refreshments and arrive early. If you’re lucky, you might even spot a seal bobbing in the water. For a quiet retreat with stunning views, Lobsterville Beach is one of Martha’s Vineyard’s best-kept secrets.

7. Polly Hill Arboretum

Tucked away in West Tisbury, Polly Hill Arboretum is a must-visit for nature lovers. This 70-acre botanical garden is home to rare and exotic trees, colorful flower gardens, and peaceful walking trails. Founded by horticulturist Polly Hill, the arboretum showcases plants from around the world that thrive in Martha’s Vineyard’s unique climate. You’ll find towering magnolias, vibrant azaleas, and even a hand-planted redwood tree.

Wandering through the gardens, I was struck by the sheer variety of plant life. Informational plaques along the trails make it easy to learn about the different species, and guided tours offer even deeper insights. It’s especially magic during fall on the Cape, when the leaves change colors. Whether you’re a plant enthusiast or just looking for a quiet place to relax, Polly Hill Arboretum is a peaceful escape from the island’s busier attractions. Bring a camera—there’s no shortage of beautiful spots here.

8. Vineyard Haven

For a mix of history, shopping, and waterfront views, Vineyard Haven is one of the best places to explore on Martha’s Vineyard. This harbor town is home to independent bookstores, boutique shops, and great Cape Cod restaurants, all within walking distance of the ferry terminal. It’s a great place to browse for handcrafted goods, from island-made jewelry to local artwork. The town also has a vibrant maritime history, with wooden boat-building traditions still alive today.

One of my favorite stops was Bunch of Grapes Bookstore, a cozy shop filled with local literature and bestsellers. I also grabbed a coffee at Black Dog Tavern, an island staple with unbeatable harbor views. Whether you’re here for a quick visit or a leisurely day of shopping and dining, Vineyard Haven offers a perfect blend of small-town charm and coastal beauty.

9. Oak Bluffs Arts District

For a vibrant and creative side of Martha’s Vineyard, head to the Oak Bluffs Arts District. This lively neighborhood is home to a mix of galleries, artist studios, and craft shops, showcasing everything from contemporary paintings to handmade jewelry. On select Saturdays in summer, the area comes alive with Art Strolls, where visitors can meet artists, enjoy live music, and browse one-of-a-kind pieces.

I spent an afternoon exploring The Featherstone Center for the Arts, an inspiring space with rotating exhibits and art workshops. Nearby, Galaxy Gallery featured stunning local photography that perfectly captured the island’s beauty. Even if you’re not an art collector, wandering through this district offers a glimpse into the creative spirit of Martha’s Vineyard. Whether you pick up a painting or just soak in the atmosphere, this artsy enclave is well worth a visit.

10. Island Alpaca

For a fun and unique experience, Island Alpaca in Vineyard Haven offers the chance to get up close with adorable alpacas. Home to over 50 fluffy residents, the farm lets visitors learn about alpaca care, breeding, and the process of turning their soft fleece into cozy products. Guided tours provide insight into these gentle animals, and the farm shop sells alpaca wool scarves, hats, and blankets.

I visited on a sunny afternoon and couldn’t resist taking selfies with the curious alpacas. They’re friendly and love to interact, making this a great activity for families and animal lovers. The farm also hosts alpaca yoga, where you can stretch and relax while surrounded by these calm creatures. Whether you stop by to pet them or pick up a handmade souvenir, Island Alpaca is a delightful escape from the typical beach day.

11. Farm-to-Table Dining at The Grey Barn

For a truly Martha’s Vineyard dining experience, The Grey Barn & Farm in Chilmark offers farm-to-table meals straight from their organic fields. This family-run dairy farm produces award-winning cheeses, fresh vegetables, and pasture-raised meats, all used in their seasonal dishes. Visitors can tour the farm, sample handcrafted cheeses like Prufrock and Bluebird, and shop for artisanal goods in their farm store. They also offer workshops on sustainable farming and cheesemaking, adding to the experience.

I stopped by for a cheese-tasting and left with a bag full of fresh bread, jams, and creamy Brie. The farm’s laid-back setting, with grazing cows and rolling pastures, makes for a perfect afternoon escape. It’s something you can do anytime of year, including during a winter on Cape Cod. Whether you’re grabbing a picnic spread or indulging in their famous wood-fired pizza nights, The Grey Barn is a must-visit for food lovers looking for authentic island flavors.

12. Edgartown Lighthouse Beach

One of Martha’s Vineyard’s most iconic spots, Edgartown Lighthouse Beach combines history, scenery, and relaxation. Located at the entrance of Edgartown Harbor, this sandy beach offers calm waters, scenic walking paths, and a close-up view of the Edgartown Lighthouse, a historic structure dating back to 1828. The lighthouse is open for tours in summer, offering panoramic views of the harbor and nearby Chappaquiddick Island.

I took an early morning walk along the shoreline, enjoying the peaceful atmosphere before the crowds arrived. Families were already setting up for the day, and paddleboarders drifted lazily across the water. After a swim, I wandered into downtown Edgartown, just a short stroll away, for a lobster roll at Among the Flowers Café. Whether you visit for a relaxing beach day or a photo-worthy lighthouse tour, this spot is a quintessential Martha’s Vineyard experience.

FAQs about the Amazing Things to Do in Martha’s Vineyard

Looking for more fun ideas on what to do in Martha’s Vineyard? Here are some popular questions (and answers) I get that will help you plan your trip to Martha’s Vineyard:

What’s the best time to visit Martha’s Vineyard?

The best time to visit Martha’s Vineyard is during the late spring to early fall, roughly from May to September. This period offers pleasant weather for outdoor activities, blooming flora, and lively events. While the summer months are peak tourist season, late spring and early fall provide a quieter and equally enjoyable experience.

How do I get to Martha’s Vineyard?

To reach Martha’s Vineyard, you can take a ferry from mainland Massachusetts, specifically from ports like Woods Hole, Falmouth, or Hyannis. Alternatively, you can fly into Martha’s Vineyard Airport (MVY) from various cities on the U.S. East Coast. On the island, transportation options include rental cars, taxis, buses, and bikes.

Is Martha’s Vineyard family-friendly?

Absolutely! With a plethora of coolest activities in Martha’s Vineyard, there’s something for everyone in the family to enjoy. What are the must-see attractions?

From the iconic Edgartown Lighthouse to the bustling streets of Oak Bluffs, there are numerous Martha’s Vineyard places to visit that you won’t want to miss.

Why do celebrities go to Martha’s Vineyard?

Celebrities flock to Martha’s Vineyard for its perfect blend of seclusion and luxury. The island offers a tranquil escape from the spotlight, with private beaches and upscale amenities. Yet, it’s also a vibrant cultural hub, making it an ideal setting for both relaxation and inspiration. It’s the ultimate VIP getaway.

How many days should I spend at Martha’s Vineyard?

The ideal duration for a visit to Martha’s Vineyard depends on what you want to experience, but for most visitors, 3 to 5 days allows for a comprehensive exploration of the island. Here’s a general breakdown:

1-2 Days:

• Explore one or two of the main towns, such as Edgartown, Oak Bluffs, or Vineyard Haven.
• Visit a beach, like South Beach or Menemsha Beach.
• Take a stroll around the iconic gingerbread cottages in Oak Bluffs.
• Dine at a local restaurant and enjoy fresh seafood.

3-4 Days (adding to the above):

• Explore all the main towns, including the more up-island areas like Chilmark and Aquinnah.
• Visit the Aquinnah Cliffs and the Gay Head Lighthouse.
• Spend more time at different beaches or engage in water activities like kayaking or paddleboarding.
• Take a bike ride or hike on some of the island’s trails.
• Explore some of the island’s farms and enjoy local produce.
• Attend a local event or festival if your visit coincides with one.

5+ Days (adding to the above):

• Dedicate a day to a specific activity, such as fishing or a guided tour.
• Explore more off-the-beaten-path areas and hidden beaches.
• Visit art galleries, museums, and cultural sites.
• Take leisurely strolls, relax on the beach, and truly soak in the island’s laid-back vibe.
• Consider day trips to nearby places, like Chappaquiddick Island.

What is Martha’s Vineyard best known for?

1. Presidential Retreat: The island has been a favorite summer vacation spot for several U.S. presidents, including Ulysses S. Grant, John F. Kennedy, Bill Clinton, and Barack Obama.
2. Beaches: Martha’s Vineyard boasts some beautiful beaches, such as South Beach in Edgartown, Menemsha Beach in Chilmark, and Joseph Sylvia State Beach between Oak Bluffs and Edgartown.
3. Historic Towns: The island is home to several charming towns, each with its own unique character. Edgartown is known for its historic homes and elegant vibe, Oak Bluffs for its colorful gingerbread cottages and lively atmosphere, and Vineyard Haven (Tisbury) as a main port and shopping area.
4. Aquinnah Cliffs: These stunning clay cliffs, located in the town of Aquinnah, are a natural wonder and a popular tourist attraction.
5. Fishing: The island has a rich fishing heritage, with Menemsha being one of the last working fishing villages in New England. The annual Martha’s Vineyard Striped Bass & Bluefish Derby attracts anglers from all over.
6. Festivals and Events: Martha’s Vineyard hosts various events throughout the year, including the Martha’s Vineyard Film Festival, the Agricultural Fair, and the Food & Wine Festival.
7. Celebrities: Beyond presidents, the island has long been a retreat for celebrities, artists, writers, and other notable figures seeking a quiet and scenic getaway.

Is it worth it to go to Martha’s Vineyard?

Absolutely, Martha’s Vineyard is a must-visit destination that offers something for everyone. From its stunning beaches and scenic bike trails to its rich history and vibrant arts scene, the island provides a distinctive blend of relaxation and adventure. It’s a trip that promises lasting memories and is worth every penny.