Martha’s Vineyard in Motion: Biking, Beaches & Creative Communities

Published byEmily Thompson

Martha’s Vineyard is an island that blends beautiful beaches, quirky towns, and a surprising mix of culture and history. Just south of Cape Cod, this Massachusetts spot has everything from Oak Bluffs’ famous gingerbread cottages to the wild, windswept cliffs of Aquinnah. If you’re into classic New England, you’ll probably find something you love here.

From sandy stretches and old lighthouses to farm stands, museums, and seafood that puts most places to shame—there’s a lot packed onto this island. Whether you’re squeezing in a quick visit or settling in for a week, the Vineyard has a little something for everyone: families, couples, solo wanderers, you name it.

Your time here could mean poking around tiny villages, hiking along the coast, or sampling the island’s mix of laid-back and upscale. Each of the six towns has its own quirks, so you might want to sample a few to get the full vibe.

Explore Iconic Towns and Villages

The Vineyard’s six towns each have their own style. Edgartown feels historic and polished, while Oak Bluffs is all color and energy. Every community offers a different angle on island life.

Discover Edgartown

Edgartown is the most historic (and honestly, the most polished) town on the island. Cobblestone streets wind past white captain’s houses from the old whaling days.

Main Street and Water Street are lined with shops—boutiques, art galleries, and more. Many are tucked into old buildings, which adds a bit of charm you just can’t fake.

Key Attractions in Edgartown:

  • Edgartown Lighthouse (10-minute walk from downtown)
  • Chappaquiddick Ferry (connects to Chappaquiddick Island)
  • Historic Whaling Church
  • Vincent House Museum

The lighthouse sits at the end of North Water Street, overlooking the harbor. You can wander right up to it and hang out on the beach nearby.

Hop on the tiny ferry to Chappaquiddick Island for quiet beaches and Cape Poge Lighthouse. Ferries run pretty much all day in summer.

Experience Oak Bluffs

Oak Bluffs is famous for its gingerbread cottages and a summer scene that can feel like a festival some nights. The Camp Meeting Association area is where you’ll find the best cluster of these wild, candy-colored Victorian houses.

The Flying Horses Carousel claims the title of America’s oldest platform carousel (it’s been spinning since 1876). Kids and adults both seem to love it.

Circuit Avenue is the main drag—restaurants, shops, ice cream, bars, you name it. There are laid-back spots and places to splurge, depending on your mood.

Must-See Oak Bluffs Spots:

  • Gingerbread cottages at Trinity Park
  • Oak Bluffs Harbor and ferry terminal
  • Ocean Park bandstand
  • Inkwell Beach

Inkwell Beach isn’t just a pretty stretch of sand; it’s got real history as one of the first integrated beaches in New England. The water’s gentle, so families flock here.

Stroll Through Vineyard Haven

Vineyard Haven (locals call it Tisbury) is the island’s year-round hub. Even when summer’s over, this town keeps humming along.

Main Street mixes practical shops with local favorites—think bookstores, coffee, and places that cater to the folks who actually live here.

The harbor’s always busy, with ferries coming and going and fishing boats at work. It feels a bit more “real” than some of the other towns.

Vineyard Haven Highlights:

  • Black Dog Tavern and General Store
  • Bunch of Grapes Bookstore
  • West Chop Lighthouse
  • Martha’s Vineyard Museum

West Chop Lighthouse is perched on the harbor’s western tip. You can’t go inside, but it’s easy to spot from the road.

The town connects easily to the rest of the island by bus, so a lot of people use it as a base for exploring.

Visit Aquinnah and Menemsha

Aquinnah has the island’s showstopper: the clay cliffs. These rise up 150 feet, streaked with colors you probably didn’t expect to see in Massachusetts.

Gay Head Lighthouse sits on top of the cliffs, open for tours in summer. Built in 1856, it’s got one of the best views around.

Moshup Beach stretches out below the cliffs—a great spot for a long, sandy walk with those crazy cliff views.

West Tisbury and Menemsha Attractions:

  • Aquinnah Cliffs overlook
  • Gay Head Lighthouse tours
  • Menemsha fishing village
  • Beetlebung Corner

Menemsha is a tiny working fishing village in Chilmark. The harbor’s full of boats and lobster traps, and the seafood here is about as fresh as it gets.

Watching the sunset from Menemsha Beach is a bit of a local tradition. People actually clap when the sun finally drops below the horizon—can’t say I blame them.

The drive between these up-island towns takes you past rolling farmland and ancient stone walls. It’s a side of the Vineyard that feels a world away from the busy beaches.

Unmissable Martha’s Vineyard Landmarks

This island’s got some real icons—lighthouses, gingerbread houses, those wild red cliffs at Aquinnah, and a huge iron tabernacle that’s basically the heart of Oak Bluffs. Somehow, it all fits together.

Lighthouses of Martha’s Vineyard

There are five historic lighthouses scattered across the island, each with a different story and view. Edgartown Lighthouse is a short walk from downtown, sitting at the harbor’s edge.

The white cast-iron tower overlooks the water, and you can stroll right up to it from the beach.

East Chop Lighthouse sits between Oak Bluffs and Vineyard Haven. The Martha’s Vineyard Museum takes care of this one. It’s open on summer Sunday evenings, but you can check it out from the road any time.

West Chop Lighthouse marks Tisbury’s western edge. It’s not open for tours, and you’ll only get a glimpse from the road, so maybe skip unless you’re already close by.

Gay Head Light at the Aquinnah Cliffs is the most dramatic. In summer, you can climb to the top for six bucks. Even if you don’t, the grounds are open all year, and the view is wild.

All the lighthouses are on the National Register of Historic Places. They still use those classic Fresnel lenses to guide boats—how cool is that?

Aquinnah Cliffs and Gay Head Light

The Aquinnah Cliffs are probably the Vineyard’s most famous sight. These streaked cliffs tower over the Atlantic, layers of red, orange, yellow, and gray clay stacked up over millions of years.

An overlook makes it easy to soak in the views of the cliffs, lighthouse, and Moshup Beach. Food stands and little shops cluster near the parking lot—expect a crowd on sunny days.

Gay Head Light sits right on the cliffs. Built in 1856, it’s still shining with its original Fresnel lens, and its beacon can be seen 24 miles out at sea.

You can walk from the overlook to the lighthouse in about 10 minutes. The path is well-marked, and summer tours run several days a week for $6 a pop.

Parking here costs $20 in summer, and it fills up fast. If you’re coming for sunset, get there early.

Historic Gingerbread Houses

Oak Bluffs has the country’s biggest cluster of “gingerbread” cottages—tiny, brightly painted Victorian houses with woodwork so detailed it almost looks edible.

The Martha’s Vineyard Camp Meeting Association area is the heart of it all. Over 300 little houses are packed into this neighborhood, each one with its own wild color scheme and carved trim.

Seaview Avenue, heading toward Edgartown, has even fancier versions—bigger and even more over-the-top with their paint and woodwork.

These cottages started out as tents for religious camp meetings back in the 1860s. Families eventually swapped canvas for wood, and now the houses sell for over a million bucks, even though they’re tiny.

Wander the winding streets and take your time. Each cottage has its own personality, and you’ll spot details you missed if you rush.

Tabernacle at Martha’s Vineyard Camp Meeting Association

The iron Tabernacle sits in the middle of the gingerbread cottages. Built in 1879, it replaced earlier wooden versions and has this huge, open-air, octagonal design.

It’s 130 feet across, seats 3,000, and the cast-iron frame holds up a tent-like roof with no posts in the way. The engineering is pretty wild for its era.

In summer, the Tabernacle hosts:

  • Wednesday night sing-alongs
  • Concerts—folk, classical, gospel, you name it
  • The famous Grand Illumination in August
  • Sunday morning worship

The Camp Meeting Association still runs the place, making it one of the oldest continuously used camp meeting sites in the country.

Feel free to wander through during the day. The iron arches and metalwork are worth a look, even if you’re not there for an event.

Experience the Island’s Best Beaches and Coastal Spots

The Vineyard has miles of coastline, with a beach for just about every mood. You’ll find everything from big Atlantic waves at South Beach to the calm, family-friendly waters of State Beach. The island’s harbors add their own kind of magic, too.

Relax at South Beach and Katama Beach

South Beach and Katama Beach are actually one long, three-mile stretch in Edgartown. You can get two totally different vibes here, depending on which side you pick.

The ocean side has big, rolling waves and sand dunes. If you’re looking for that classic beach feel (and maybe a little surfing), this is your spot.

Why it stands out:

  • Three miles of soft, white sand
  • Atlantic Ocean on one side
  • A protected salt pond on the other
  • Free street parking (though it goes fast in summer)

The protected side faces a salt pond—calm water, perfect for families with little kids or anyone who prefers a gentler swim.

You can bike here from downtown Edgartown in about four miles. That’s probably your best bet if you want to skip the parking hunt on busy days.

The beach is long enough that, even on crowded weekends, you can usually find a spot to call your own.

Visit State Beach and the Jaws Bridge

Joseph Sylvia State Beach stretches along the road between Edgartown and Oak Bluffs. If you’ve seen Jaws, you’ll spot this place right away.

That iconic bridge scene? Filmed right here. Kids still leap off the bridge into Sengekontacket Pond below—just like in the movie, though maybe with a little more hesitation from parents these days.

Beach features:

  • Super easy roadside access
  • Calm, shallow water—great for kids
  • The legendary “Jaws Bridge”
  • Nice views across the pond

The water’s shallow for a good distance out, so families can relax a bit more. It’s honestly one of the safest swimming spots on the island.

Parking’s right along Beach Road. Since the beach hugs the main road, you pretty much just step out and you’re there.

Bridge jumping is a rite of passage for some, but please—check the water depth and current before you take the plunge.

Explore Vineyard Haven Harbor and Sengekontacket Pond

Vineyard Haven Harbor is the main ferry hub and a real working harbor. You’ll spot everything from tiny sailboats to hulking ferries coming and going all day.

The waterfront’s walkable, with boats to watch and plenty of food or shopping nearby in downtown.

Harbor highlights:

  • Busy ferry terminal
  • Waterfront dining
  • Boat watching
  • Easy to walk around

Sengekontacket Pond connects to State Beach and has calm waters for kayaking. It’s way less rough than the ocean beaches.

This big saltwater pond sits between Edgartown and Oak Bluffs. It’s perfect for paddle sports or just zoning out by the water.

You’ll find several access points along Beach Road, so it’s easy to pair a visit here with some beach time.

Outdoor Adventures and Active Pursuits

Martha’s Vineyard packs in miles of scenic bike paths, hiking trails through wildlife sanctuaries, great fishing and boating, and even championship golf. The island’s mix of landscapes gives outdoor lovers plenty to chew on.

Scenic Biking Trails and Tours

There are over 40 miles of paved bike paths connecting the main towns. You can pedal from Vineyard Haven to Oak Bluffs, or take the scenic route from Edgartown to South Beach.

Popular Biking Routes:

  • Vineyard Haven to Oak Bluffs (3 miles)
  • Edgartown to South Beach (4 miles)
  • Oak Bluffs to Edgartown (6 miles)

Many folks rent bikes right at the ferry. It’s honestly the easiest way to start exploring as soon as you land.

Most bike paths are flat, so families with kids can handle them. You’ll cruise through forests, past ponds, and along some pretty stunning coastline.

If you want some local insight, several companies run guided bike tours. They usually last a couple of hours and hit all the main sights.

Hiking and Wildlife Sanctuaries

Martha’s Vineyard has some great hiking in protected spots. Manuel F. Correllus State Forest sits in the island’s center with over 5,000 acres and lots of trails.

The forest mixes easy paths with some tougher hikes. Expect pine, oak, and quiet ponds all around.

Felix Neck Wildlife Sanctuary has three miles of trails through marsh, woods, and waterfront. It’s on 200 acres and feels peaceful, especially if you’re into birdwatching.

You might spot ospreys, herons, and plenty of other birds. The visitor center hands out trail maps and tips about local wildlife.

Long Point Wildlife Refuge gives you two miles of trails down to a gorgeous beach, cutting through grasslands and scrub along the way.

Cape Poge Wildlife Refuge on Chappaquiddick Island is a bit more off the beaten path. You’ll need to hop a short ferry to get there, but it’s worth it for the quiet.

Boating and Fishing Excursions

The waters around Martha’s Vineyard are a playground for fishing and boating, pretty much all year. You can charter a boat for deep-sea fishing or just try your luck surfcasting from the shore.

People love fishing off Gay Head and around Chappaquiddick. In summer, striped bass, bluefish, and fluke are the usual catch.

Got boating experience? Several marinas rent boats—Edgartown Harbor and Vineyard Haven Harbor are the main spots.

Fishing charters run half-day or full-day trips. Captains know the secret spots and provide all the gear, so you just show up and fish.

Shore fishing’s also popular at places like South Beach and Wasque Point.

Keen to kayak? Rentals are easy to find, especially around quieter waters like Sengekontacket Pond. It’s calm, so beginners won’t feel out of their depth.

Golfing on the Island

Martha’s Vineyard is home to several golf courses with ocean views and layouts that keep things interesting. There are public courses and private clubs that welcome visitors, so you don’t need a membership to play.

Mink Meadows Golf Club is a 9-hole course with pretty views of Vineyard Sound. It’s semi-private but open to the public, and the vibe is laid-back.

The course has rolling fairways and greens that are kept in good shape. Ocean breezes and scenery make it a nice place for a round.

Farm Neck Golf Club is a full 18-hole championship course—it’s even hosted PGA Tour events. You’ll get water views and a solid challenge if you’re a serious golfer.

Most courses offer lessons and rental gear. Booking tee times in advance is smart during summer when things get busy.

The island’s weather is mild enough for golf from spring through fall. Early mornings and late afternoons are usually the most comfortable.

Cultural Experiences, Museums, and Local Heritage

The island’s culture shines through its main museum, historic sites, and deep ties to the Wampanoag tribe. Artisan shops and local markets pop up in every town, adding to the experience.

Martha’s Vineyard Museum and Historical Sites

The Martha’s Vineyard Museum is a great place to start if you want to dig into the island’s story. At 151 Lagoon Pond Road in Vineyard Haven, it covers Native American heritage and maritime history with hands-on exhibits.

Check out the Carnegie Heritage Center in Edgartown for a look at the town’s whaling roots. They run guided walking tours Tuesday through Saturday at 11 am.

The MVCMA Cottage Museum in Oak Bluffs lets you peek inside those famous gingerbread cottages. These bright homes are tied to the religious revival movement that shaped the area.

The Gay Head Lighthouse at Aquinnah sits on dramatic cliffs and offers both history and sweeping ocean views.

Cultural Tours and the Wampanoag Tribe

The African American Heritage Trail guides you to locations across the island, highlighting the impact of African Americans on Martha’s Vineyard.

Head to the Aquinnah Cultural Center to learn about the Wampanoag tribe’s traditions. Their exhibits, workshops, and programs honor ancestral stories and customs.

The Vineyard Haven Public Library keeps special collections—rare books and old photos for anyone curious about the island’s cultural evolution.

Walking tours from the Carnegie Center connect you with local guides and historical artifacts. They’re affordable and often full of interesting tidbits you won’t find in a brochure.

Artisan Shops and Local Markets

Every town has its own shopping scene, with local makers and craftspeople selling their work. Oak Bluffs has galleries and studios where you can meet artists in person.

The Featherstone Center for the Arts in Oak Bluffs is a hub for the island’s creative crowd. There are workshops, exhibits, and events all year round.

Edgartown’s historic streets are lined with boutiques selling handmade jewelry, pottery, and textiles—much of it crafted by islanders.

Vineyard Haven’s seasonal farmers markets are a good place to buy produce and crafts straight from the source. There’s something special about meeting the people behind the products.

Family-Friendly & Iconic Island Activities

Martha’s Vineyard has classic attractions that capture the island’s charm for all ages. From the oldest carousel in the country to friendly alpacas and beloved local treats, these activities stick with you.

Ride the Flying Horses Carousel

The Flying Horses Carousel in Oak Bluffs is America’s oldest operating platform carousel, running since 1876. The hand-carved wooden horses have been making kids smile for nearly 150 years.

You’ll find it at 15 Oak Bluffs Avenue, open during the summer. Rides are just a few bucks, so it’s an easy family outing.

What makes it special:

  • Original horses still sport real horsehair manes
  • The brass ring game gives lucky riders a free spin
  • Great for kids 4 and up who can sit on their own

The painted horses go up and down as you circle. Kids always try to snag the brass ring for a free ride, and parents appreciate the low price and quick fun. It’s a good stop between other adventures.

Visit Island Alpaca and Farm Tours

Island Alpaca Company covers 19 acres in Oak Bluffs and is home to dozens of gentle alpacas. Visitors can walk these animals around the farm and learn about their quirky personalities and care.

Age requirements for alpaca walks:

  • Under 14: Must walk with parent or guardian
  • Ages 14+: Can lead alpacas solo

The farm shop sells alpaca wool products—scarves, hats, and blankets that are ridiculously soft.

Other local farms offer their own spin. Morning Glory Farm in Edgartown has pumpkin picking and tours in season. Grey Barn and Farm focuses on sustainable farming and fresh produce.

These visits give kids a hands-on look at farming and animal care. Most farms charge a small fee for tours and activities.

Unique Local Treats: Mad Martha’s Ice Cream and Back Door Donuts

Mad Martha’s Ice Cream serves up homemade flavors at a few locations around the island. They mix up classics and creative seasonal options. The shops are bright and always buzzing with families.

Popular flavors include:

  • Mud Pie – chocolate ice cream with fudge bits
  • Beach Plum – made from local berries
  • Vineyard Vanilla – extra rich vanilla bean

Back Door Donuts in Oak Bluffs opens late at the back of a restaurant. It feels like a secret adventure, especially for kids staying up past bedtime.

They start making donuts fresh around 7:30 PM. Apple cider donuts, glazed, and seasonal flavors are all on the menu. The casual vibe and late hours make it a local favorite.

Both spots keep prices reasonable for what you get. They’re perfect stops during a bike ride or a nighttime stroll.

Day Trips, Getting Here, and Practical Tips

Martha’s Vineyard is easy to reach by ferry from several Cape Cod towns. The Steamship Authority runs year-round boats from Woods Hole and seasonal trips from Falmouth and New Bedford. You can also get here from New York City with a bus-ferry combo, or plan island-hopping adventures to nearby Nantucket.

Arriving by Ferry: Steamship Authority and More

The Steamship Authority runs the main ferry service to Martha’s Vineyard all year. Ferries leave from Woods Hole, heading to both Vineyard Haven and Oak Bluffs.

Ferry Schedule Basics:

  • Peak season: Ferries depart every 30-45 minutes
  • Off-season: Service slows down, usually hourly
  • Travel time: 45 minutes from Woods Hole

You can bring your car on the Steamship Authority ferries, but you’ll need to book ahead—especially in summer. Walk-on passengers usually don’t need reservations, unless it’s a busy weekend.

Other Ferry Options:

  • Hy-Line Cruises from Hyannis (seasonal, passengers only)
  • Island Queen from Falmouth (seasonal, passengers only)

If you’re going for just a day, grab the earliest ferry you can. The 8:00 AM boat gives you the most time to explore. Ferries back to the mainland run into the evening, with the last one around 9:00 PM during summer.

Exploring Connections: From Cape Cod, Woods Hole, and New Bedford

Cape Cod is pretty much the main launchpad to Martha’s Vineyard. Woods Hole in Falmouth is the go-to spot, with year-round ferries and parking that’s easy—well, unless it’s July and everyone’s there.

From Woods Hole:

  • Free parking fills up fast in summer
  • Paid lots are close by
  • MBTA bus links to Boston

From Falmouth: The Island Queen makes a quick 35-minute hop to Oak Bluffs. It’s a solid pick if you want to land right in the middle of the island’s most walkable town.

From New Bedford: The Steamship Authority runs seasonal ferries from New Bedford to Oak Bluffs. The trip takes about 1.5 hours, but the coastal scenery is worth it.

Parking in New Bedford is easier and usually cheaper than Cape Cod. Fewer crossings mean you have to plan your timing a bit more carefully.

Planning a Trip from New York City or Nantucket

From New York City: A few companies offer bus-ferry combo packages from Manhattan to Martha’s Vineyard. These bundle your ride to Cape Cod with ferry tickets.

The whole trip takes about 6-7 hours. You could also drive up yourself—figure about 4.5 hours to the Cape, then hop on a ferry.

Peter Pan Bus Lines runs direct service from New York to Woods Hole and includes the ferry connection.

From Nantucket: Hy-Line Cruises connects Nantucket and Martha’s Vineyard in the summer. The ride is about 2.5 hours with a stopover in Hyannis.

This route is perfect for island-hopping in Massachusetts. Why not see both islands if you’re already in New England?

Seasonal Schedule Note: Inter-island ferries usually run from late May through October. Schedules can shift with weather and crowds, so double-check before you go.

Enjoying the Island’s Culinary Scene

Martha’s Vineyard is packed with fresh seafood and classic spots that really show off the island’s coastal vibe. Waterfront restaurants in Menemsha serve up the daily catch with some pretty unbeatable harbor views. The Black Dog Tavern? That’s a must for the full New England experience.

Seafood and Dockside Dining in Menemsha

Menemsha is where you go for the freshest seafood—no contest. This little fishing village hugs the island’s western shore, and you can see the boats coming in with the day’s haul.

Larsen’s Fish Market is the go-to for lobster rolls and fried clams. You can watch the crew unload their catch right outside. They sell both cooked and raw seafood, so take your pick.

The Bite keeps it casual with picnic tables outside. Their fish and chips come straight from the harbor, and the scallops are especially sweet and tender.

Menemsha Beach Restaurant gives you table service with water views. Steamers, lobster, and striped bass—often caught that morning—are all on the menu. Dinner here at sunset? Can’t beat it.

Most places close up shop by 8 PM, so get there early in summer. And heads up: a lot of restaurants only take cash, so bring some bills just in case.

The Black Dog Tavern Experience

The Black Dog Tavern has been a Martha’s Vineyard staple since 1971. You’ll spot it right on the Vineyard Haven harbor, with a breezy outdoor deck that’s hard to beat.

Expect classic New England favorites like fish and chips, lobster bisque, and steamers. They pull in a lot of their seafood from local waters—always a plus. And if you’re the type who likes a souvenir, their famous t-shirts and merch are everywhere.

It does get packed in the summer, so dinner reservations are smart. Breakfast and lunch? Usually a bit easier to snag a table.

Popular menu items include:

  • New England clam chowder
  • Lobster roll with fries
  • Pan-seared scallops
  • Fish tacos

The vibe’s relaxed, perfect for families or a casual date. Dogs can hang out with you on the deck, which, honestly, feels just right for a place like this.