The first time I stepped off the ferry onto Martha’s Vineyard, I immediately understood why this island has been a longtime escape for presidents, writers, and anyone craving a slower pace by the sea. With its pastel-colored gingerbread cottages, windswept beaches, historic lighthouses, and charming harbor towns, the Vineyard feels both timeless and refreshing. Whether you’re visiting for a single day or settling in for a week, there’s no shortage of ways to experience the island’s beauty.
In this guide, I’ll walk you through my favorite things to do in Martha’s Vineyard from beach-hopping and biking through scenic trails to exploring the island’s historic towns and indulging in fresh seafood. I’ll also share travel tips and even a sample one-day itinerary to help you make the most of your visit.
Explore the Charming Towns of Martha’s Vineyard
Oak Bluffs and Its Gingerbread Cottages
Oak Bluffs is often the liveliest town on the island, and it was my very first stop on Martha’s Vineyard. What struck me immediately were the gingerbread cottages more than 300 of them clustered together around the Martha’s Vineyard Camp Meeting Association. Each cottage is painted in bright candy-colored hues, with intricate woodwork that makes them look like frosted gingerbread houses. Wandering here feels like stepping into a storybook, and every corner has a picture-perfect photo opportunity.
In the summer months, the Tabernacle, a massive open-air iron structure in the heart of the Campgrounds, hosts concerts, sing-alongs, and cultural events that bring the community together. At night, many of the cottages are lit with lanterns, which makes for a magical evening stroll.
But Oak Bluffs is more than just cottages it’s also home to the Flying Horses Carousel, the oldest operating platform carousel in the U.S. Riding it is pure nostalgia, especially for kids, but even as an adult, I couldn’t resist trying to catch the brass ring. Afterward, I grabbed ice cream at Mad Martha’s and walked down to Inkwell Beach, a historic beach near town that’s perfect for swimming or a quick dip.
Oak Bluffs has a lively waterfront filled with restaurants, bars, and ferry access. If you’re visiting for just a day, this is a great place to base yourself.
Edgartown and Its Historic Whaling Past
If Oak Bluffs is whimsical, Edgartown is elegant. This town was once one of the busiest whaling ports in New England, and you can still feel its history in the beautifully preserved captain’s houses that line the streets. Many of these 19th-century homes are now inns, boutiques, or private residences, but they’ve retained their white clapboard exteriors and classic New England charm.
I loved strolling down North Water Street, where every house seems to tell a story of the island’s seafaring past. Edgartown is also one of the best shopping towns on Martha’s Vineyard, with upscale boutiques, art galleries, and independent shops that carry everything from nautical-inspired home décor to Vineyard-made jewelry.
Of course, food is a highlight here. I had some of the freshest oysters I’ve ever tasted at The Seafood Shanty, paired with harbor views that made it even more memorable. Edgartown is also a fantastic dining spot if you’re staying overnight, with a mix of casual clam shacks and fine dining.
Just a short walk from downtown is the Edgartown Lighthouse, which sits at the end of a sandy path overlooking the harbor. Climbing to the top gave me one of the best panoramic views on the island, especially at sunset.
Local Tip: From Edgartown, you can take a short ferry over to Chappaquiddick Island (“Chappy”), where you’ll find serene beaches, the Mytoi Japanese Garden, and Cape Poge Lighthouse.
Vineyard Haven
Vineyard Haven is the island’s year-round working town and one of the main ferry ports, which means most visitors pass through at some point. While it’s often overlooked in favor of Oak Bluffs or Edgartown, I found it to be incredibly charming once I slowed down to explore.
The heart of Vineyard Haven is its Main Street, lined with independent bookstores, art galleries, and cozy cafés. I spent an afternoon browsing Bunch of Grapes Bookstore, a local institution that’s been around since 1970, followed by a stop at Mocha Mott’s for a coffee.
One of the town’s biggest icons is The Black Dog Tavern, which started in 1971 and helped put Vineyard Haven on the map. The tavern serves hearty breakfasts and seafood dinners, and its logo has become a recognizable symbol of the island. You’ll see Black Dog apparel everywhere I couldn’t resist taking home a hoodie as a souvenir.
Vineyard Haven also has a more local, less touristy feel compared to Oak Bluffs or Edgartown. The harbor is always busy with fishing boats and ferries, giving you a sense of the island’s working rhythm. For travelers who prefer a quieter base with easy ferry access, Vineyard Haven makes a great choice.
If you’re into art, check out the Martha’s Vineyard Playhouse or the Vineyard Haven Harbor Cultural District they often have rotating exhibits, performances, and events.
Visit the Island’s Lighthouses
Martha’s Vineyard has five historic lighthouses, and visiting them was one of my favorite ways to explore the island. Each one tells a piece of Vineyard history while offering some of the best coastal views.
Gay Head Lighthouse (Aquinnah)
Perched above the famous Aquinnah Cliffs, this lighthouse is the most dramatic of them all. I arrived just before sunset, and the cliffs glowed in shades of red, orange, and gold it felt like the island was putting on a show just for me. The lighthouse itself dates back to 1799 (though it was rebuilt in 1856), and it has guided sailors through these waters for centuries. The walk to the viewing area is easy, and the reward is an unforgettable panorama of Vineyard Sound.
Edgartown Lighthouse
Located right at the edge of Edgartown Harbor, this lighthouse is the easiest to visit if you’re short on time. The sandy path leading up to it felt peaceful, especially in the early morning when the harbor was still. You can climb inside seasonally, and the views from the top stretch across Chappaquiddick Island.
East Chop Lighthouse
Just a short drive or bike ride from Oak Bluffs, East Chop sits on a bluff overlooking Vineyard Sound. I found it quieter than Edgartown, with fewer tourists, which made it the perfect spot for an evening walk. If you’re into photography, sunset here is spectacular the lighthouse silhouette against the sky is stunning.
West Chop Lighthouse
This one is a little more tucked away in Vineyard Haven and isn’t always open to the public, but you can still admire it from the outside. West Chop feels more rugged and less polished, and I liked that it gave me a sense of the island’s working maritime history.
Cape Poge Lighthouse (Chappaquiddick Island)
For the adventurous, Cape Poge is a gem worth seeking out. Located on Chappaquiddick Island, it’s only accessible by ferry and often requires a four-wheel-drive tour along the sandy dunes. It felt like an off-the-beaten-path adventure, and the lighthouse itself has an unspoiled, windswept beauty.
Zee Tip: If you’re short on time, pick Edgartown Lighthouse for convenience or Gay Head Lighthouse for the most stunning scenery. If you have a few days, try to see them all.
Relax on Martha’s Vineyard Beaches
The beaches here are as varied as the island itself some are wild and windswept, while others are calm and family-friendly. I spent a good part of my trip beach-hopping, and each one offered something different.
South Beach (Katama)
This long stretch of golden sand near Edgartown is one of the most popular beaches on the island. It’s perfect if you love big waves, body surfing, or just soaking up the sun. I visited in the late afternoon, and the energy was lively with groups of friends, families, and surfers. Be mindful that the waves can be rough, so it’s not the best for young kids.
Joseph Sylvia State Beach
This was one of my favorites because of its calm waters. Stretching for about two miles between Oak Bluffs and Edgartown, it’s ideal for swimming, kayaking, or simply floating in the warm shallows. The highlight here is the famous “Jaws Bridge,” where brave locals (and a few tourists like me!) jump into the water. Even if you don’t jump, it’s fun to watch.
Menemsha Beach
If you only make it to one beach for sunset, let it be Menemsha. I packed a picnic from one of the nearby seafood shacks (Larsen’s Fish Market is the classic choice) and joined the crowds of locals and visitors gathered on the sand. The sky lit up in shades of pink and purple, and it felt like the entire island had gathered in one spot to celebrate the end of the day.
Aquinnah Public Beach
Nestled beneath the Aquinnah Cliffs, this beach is breathtaking. The clay cliffs rise dramatically above the sand, creating a backdrop unlike anywhere else on the island. It’s a little more secluded, so it’s great if you want a quieter experience. Just note that swimming can be tricky due to currents, so it’s more about walking, photographing, and admiring the views.
Lucy Vincent Beach
If you’re staying near Chilmark, Lucy Vincent Beach is a local favorite. It’s technically restricted to residents in the summer, but outside peak season, visitors can sometimes access it. With its striking rock formations and soft sand, it felt like one of the most naturally beautiful spots I saw on the island.
Many Vineyard beaches are private or restricted to residents in high season, so always check access rules ahead of time. Public beaches like South Beach, State Beach, and Menemsha are safe bets for visitors.
Eat and Drink Like a Local
One of my favorite parts of visiting Martha’s Vineyard was the food. The island has a mix of casual seafood shacks, farm-to-table cafés, and upscale restaurants, all centered on fresh, local ingredients. You’ll never be far from a lobster roll, an oyster bar, or a scoop of homemade ice cream.
- Lobster Rolls
If there’s one thing you must eat on Martha’s Vineyard, it’s a lobster roll. I tried a few, and while everyone has their favorite, Larsen’s Fish Market in Menemsha stood out to me. Eating a lobster roll on the dock, watching fishing boats come in, felt like the ultimate Vineyard moment. For a slightly more upscale version, head to Edgartown’s Atlantic Fish & Chop House, where they serve a warm buttered roll with a side of fries. - Oysters & Seafood
The Vineyard is famous for its oysters, which are farmed right in the island’s waters. I ordered a dozen at the Martha’s Vineyard Chowder Company, and they were so fresh they tasted like the ocean itself. If you’re an oyster lover, time your trip around the Martha’s Vineyard Oyster Festival in October, when local growers and chefs showcase the best of the island’s seafood. - Ice Cream Stops
After long afternoons at the beach, I couldn’t resist a stop at Mad Martha’s or Ben & Bill’s Chocolate Emporium in Oak Bluffs. Both are local institutions, and trying their seasonal flavors (blueberry in particular) made it feel like summer in a cone. - Coffee & Breakfast
For mornings, nothing beats the Black Dog Bakery & Café in Vineyard Haven. It’s iconic not only for its pastries and coffee but also for its role in Vineyard culture. I loved starting the day with a strong coffee and one of their famous muffins before heading out to explore. - Farm-to-Table Dining
Beyond seafood, the Vineyard has a strong farming tradition. Many restaurants use produce from the island’s small farms. One memorable dinner for me was at State Road Restaurant in West Tisbury, where everything from the bread to the vegetables was sourced locally.
Reservations book up quickly in summer, especially in Edgartown and Oak Bluffs. If you’re visiting in July or August, try to book dinners at least a week in advance.
Get Active Outdoors
Martha’s Vineyard is more than just beaches and towns it’s also a playground for outdoor adventures. Whether you prefer biking, hiking, or being out on the water, there are plenty of ways to stay active.
Biking Around the Island
Biking is hands-down one of the best ways to see Martha’s Vineyard. The island has more than 40 miles of bike paths, many of them flat and scenic. I rented a bike in Oak Bluffs and rode along the coastal trail to Edgartown, stopping at Joseph Sylvia State Beach for a quick swim. The views were incredible, and it felt like the perfect balance of exercise and exploration.
Hiking Trails
For a slower pace, hiking is a great way to discover the island’s natural side. The Felix Neck Wildlife Sanctuary near Edgartown was a highlight for me I spotted herons, ospreys, and even a few deer along the trails. If you’re craving wilder landscapes, head to Long Point Wildlife Refuge, where you’ll find miles of sandy dunes, salt ponds, and secluded beaches.
Kayaking and Paddleboarding
The calm inlets around Vineyard Haven and Edgartown are perfect for kayaking or paddleboarding. I rented a kayak for a morning paddle and loved how peaceful it was gliding along the water with just the sound of seabirds overhead. For something more adventurous, you can also book guided tours that take you into less accessible coves.
Sailing Excursions
Martha’s Vineyard has a deep maritime history, and being out on the water felt like connecting with the island’s soul. I joined a sailing trip from Edgartown Harbor, and as we caught the breeze and drifted past Chappaquiddick, I understood why sailing is such a beloved tradition here. Sunset sails are especially magical, with the sky painted in soft pinks and golds.
Fishing & Clamming
For something truly local, try fishing or clamming. The Vineyard is famous for its striped bass, and I met plenty of anglers along the shore. If you prefer something interactive, families often enjoy digging for clams at low tide (permits required).
Many of the outdoor activities like kayaking, sailing, or guided hikes are seasonal. If you’re visiting outside summer, check availability in advance.
Practical Travel Tips for Visiting Martha’s Vineyard
Planning ahead can make all the difference when visiting Martha’s Vineyard, especially during peak season. Here are some things I learned that will make your trip smoother:
- Getting There:
Most visitors arrive by ferry, and the most common departure point is Woods Hole on Cape Cod. Ferries also run seasonally from New Bedford, Rhode Island, New York, and even New Jersey. If you’re bringing a car, make your reservation months in advance spots fill up quickly in summer. For those short on time, the Martha’s Vineyard Airport has small daily flights from Boston, New York, and Nantucket. Flying in gives you an incredible bird’s-eye view of the island. - Getting Around:
Bringing a car is convenient, but it’s not essential. I found the island’s bus system surprisingly efficient, with routes connecting all the main towns and beaches. Biking is also an incredible way to explore the island has miles of scenic bike paths. For quick trips, taxis and rideshares are available, though they can get pricey. - Best Time to Visit:
Summer (June–August) is when Martha’s Vineyard is at its liveliest beaches are bustling, shops and restaurants are open late, and the island hosts everything from film festivals to farmer’s markets. But if you prefer fewer crowds, September and early October are magical. The weather is still warm enough for the beach, but the island is quieter, and hotel prices drop. Spring (May–June) is also a good option for fresh blooms and cooler hikes. - Where to Stay:
Each town has a different personality. Oak Bluffs is lively and colorful, Edgartown is upscale and historic, Vineyard Haven is practical and low-key, and Chilmark/Aquinnah offer a more secluded, local feel. If you only have one or two nights, I recommend Oak Bluffs or Edgartown for the easiest access to restaurants and sights. - Packing Tips:
The Vineyard is casual but stylish. Bring light summer clothes, a sweater or jacket for cool evenings, and beach essentials. Comfortable shoes are a must if you plan to bike or explore the towns on foot. Don’t forget sunscreen and a reusable water bottle there are refill stations around the island.
Parking can be tricky in summer, especially in Oak Bluffs and Edgartown. If you can, leave the car behind and explore by bike or bus. You’ll avoid traffic and actually see more.
One-Day Itinerary for Martha’s Vineyard
Even though I recommend spending a few days here, Martha’s Vineyard is doable in a single day if you plan wisely. Here’s how I’d make the most of it:
- Morning (Oak Bluffs):
Catch an early ferry into Oak Bluffs and start your day with a coffee and muffin at Mocha Mott’s. Wander through the gingerbread cottages, and take a spin on the Flying Horses Carousel. If the weather’s nice, dip your toes in the water at Inkwell Beach before moving on. - Late Morning (Bike to Edgartown):
Rent a bike in Oak Bluffs and ride along the State Beach path toward Edgartown. This flat, scenic ride takes about 45 minutes and passes the Jaws Bridge, where you can stop to watch (or join) the cliff jumpers. - Lunch (Edgartown):
Once in Edgartown, grab lunch at The Seafood Shanty or The Wharf Pub. If you prefer something quick, pick up a lobster roll to-go and eat by the harbor. Before leaving town, stroll to the Edgartown Lighthouse for panoramic views. - Afternoon (Aquinnah):
Hop on a bus or drive to the far western side of the island to see the Gay Head Cliffs and Lighthouse in Aquinnah. The colorful clay cliffs are one of the most photographed spots on the island, and for good reason. Spend a little time browsing the shops nearby, which often sell Native Wampanoag crafts. - Evening (Menemsha):
End your day in Menemsha, a small fishing village that feels like stepping back in time. Pick up takeout from Larsen’s Fish Market. I recommend the clam chowder and lobster roll, and carry it down to the beach. As the sun dips below the horizon, you’ll be surrounded by families, couples, and locals all enjoying the same simple pleasure: a Vineyard sunset.
Optional Add-On: If you have a car, stop at West Chop Lighthouse on the way back to Vineyard Haven before catching your evening ferry.
What I love about Martha’s Vineyard is how it feels like a world away, even though it’s just a short ferry ride from the mainland. Each town has its own character, the beaches never disappoint, and the seafood is as fresh as it gets. Whether you’re visiting for a quick day trip or settling in for a long weekend, the Vineyard has a way of making time slow down. It’s one of those places that invites you to relax, explore, and savor every moment by the sea.
