15 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 15 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. See the colorful 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. Take a private island tour with a local guide

Ever wanted a local to show you the real Martha’s Vineyard? This private sightseeing tour does just that. With longtime island guide Craig behind the wheel, you’ll explore all six towns at your own pace, from colorful Gingerbread Cottages in Oak Bluffs to the dramatic Aquinnah Cliffs.

It’s a relaxed, three-hour drive in a spotless luxury minivan, with plenty of photo stops, stories, and small details you’d miss on your own. Craig tailors the route to your interests, whether that’s lighthouses, history, or local seafood shacks.

After the tour, grab oysters at Menemsha Market or stroll through Edgartown’s harbor for a postcard-perfect finish. It’s the smartest way to see the island when time is short, and it feels like spending the day with a friend who knows every corner.

3. Bike scenic trails across the island

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.

4. Watch the sunset at 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.

5. Take a boat tour of Katama Bay oyster farm

If you’ve ever wondered how oysters go from bay to raw bar, this Signature Oyster Farm tour is your front-row seat. Captain Ryan Smith, a Coast Guard licensed local with more than 15 years of experience, takes you out on a custom-built boat across Katama Bay for a hands-on look at Vineyard oyster farming.

You’ll see how these famous bivalves are grown, learn the ins and outs of shellfish cultivation, and, of course, slurp as many fresh oysters as you can while cruising the calm waters. It’s an intimate, 90-minute trip that feels more like hanging out with friends than a formal tour.

I’d bring a favorite drink (it’s BYOB) and plan to linger at Katama Landing afterward to catch the late-afternoon light over the bay.

6. Go sailing from Edgartown Harbor

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.

7. Grab a beer at 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.

8. See where JAWS was filmed with trivia and prizes

Movie buffs, this one’s too good to skip. The Jawsome JAWS Tour takes you around Martha’s Vineyard to the exact spots where Spielberg filmed his iconic shark thriller. You’ll visit beaches, wharfs, and harbors that doubled as Amity Island, with clips from the movie playing on board as you roll between locations.

Led by Alex from the original film, the four-hour tour is packed with behind-the-scenes stories, trivia contests, and plenty of photo stops. The new sound system even plays that heart-pounding JAWS theme while you explore.

I recommend grabbing lunch near Oak Bluffs before the noon departure, then snagging a seaside seat on the upper deck for the best views of those legendary filming sites. It’s pure nostalgia for any JAWS fan.

9. Swim at 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.

10. Walk through 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.

11. Shop and eat in 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.

12. Hit the galleries in 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.

13. Meet alpacas at Island Alpaca farm

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.

14. Try farm cheese 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.

15. Check out 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.

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