Gingerbread Cottages Martha's Vineyard

Whether you are staying in the island for a week or just visiting for the day during a Cape Cod vacation, Martha’s Vineyard offers some great attractions and sights to see. Oak Bluffs, the island’s most visited town, is great for seeing the famous gingerbread cottages, shopping, and exploring the lively harbor with its many restaurants, shops, and party atmosphere. A short bike ride or bus trip away, Edgartown has a vibrant downtown area with art galleries and shops, the Edgartown lighthouse, and the fishing pier where visitors can enjoy a basket of fried clams while enjoying a summer afternoon. Chappaquiddick Island and some of the best surf beaches are found in Edgartown as well.

Martha’s Vineyard has six towns, each with its own flavor and characteristics. Depending upon your mood and how much time you have to spend, you should be able to find something to enjoy in each one of them.

Knockabout Oak Bluffs Audio Tour

Take a self-paced walk through the island’s most popular town. Includes all audio files streamed directly to your smartphone. No apps, no accounts, no passwords to remember. Super easy.

Oak Bluffs

Martha’s Vineyard Camp Meeting Association (“The Campground”)

Pink House, Martha's Vineyard

The Pink House is the most photographed cottage in the Campground. It recently hit the market in 2021 for a mere $635,000. It’s not winterized, either.

Many who visit the island will want to see firsthand the famed gingerbread cottages of Oak Bluffs. These postcard-worthy summer homes began as a religious summer retreat for Methodists back in 1835 and originally was known as Wesleyan Grove. Back then, it truly was a campground, with large community tents and smaller family tents pitched on the grounds for just a few weeks of the year. Today, all of the cottages are permanent, but if you look closely, you can still see the influence of the original camping setup. Many of the homes have peaked doorways that resemble the entrance of a canvas tent as the flaps are pulled back in an effort to keep some remnant of the original camping experience.

At the center of the Campground is the Tabernacle, originally a large, open-sided tent used to shield worshippers from the hot sun during services. Today, the Tabernacle is used for community events, flea markets, and summer worship services.

You can learn more about the Martha’s Vineyard Camp Meeting Association with the Knockabout Oak Bluffs Audio Tour, or sign up with a live walking tour from the association (July and August only).

Pirate Adventures

What to do on Martha's Vineyard - Pirate Adventures

Sometimes it can be a bit difficult to find activities for the kiddos on the island. Pirate Adventures is something that you may want to take advantage of if you have little ones.  Onboard the Sea Gypsy, kids will get into pirate costumes and embark on a short voyage that includes sunken treasure and a naval battle where kids will blast the opposing pirate ship with water cannons. Adventures last approximately 90-minutes and are geared for kids ages 3-10 years old.

Pirate Adventures set sail from Oak Bluffs Harbor, so getting there is a breeze. 

Flying Horses Carousel

Another popular attraction for families is the Flying Horses Carousel, the oldest platform carousel in the nation. Originally put into service on Coney Island, the attraction was moved to the Vineyard in 1884. The horses feature real horsehair manes and the carousel’s organ still plays music from paper rolls. The horses do not move up and down, but instead, riders reach for metal rings as they pass by dispensers located around the perimeter of the ride. Try to gather the most rings in your family, and if you get a brass ring, then you get a free ride.

Get a Dirty Banana at Nancy’s

Located on Oak Bluffs Harbor, Nancy’s is one of the most popular locations in Oak Bluffs. It is home to the island’s most sought-after frozen drink – the legendary Dirty Banana. Nancy’s outdoor bar, Donovan’s Reef, serves up these delicious concoctions that visitors can enjoy while overlooking the harbor. No visit to Martha’s Vineyard is complete without one.


If you are looking for adventure, then Martha’s Vineyard Ocean Sports has you covered. Try parasailing 600 ft over Vineyard Sound for a 10-12 minute thrill. Ocean Sports also offers jet ski tours and rentals, flyboarding, and boat rentals.


Memorial Wharf

What to do on Martha's Vineyard - Edgartown Harbor

The Quarterdeck is a popular seafood shack with take-out service at Edgartown Harbor

Overlooking Edgartown Harbor and the “On Time” ferry to Chappaquiddick is Memorial Wharf. Not much official activity happens here, but it’s a great place to stop and hang out for a few minutes. Grab a basket of fried clams from the Quarterdeck next door and find a picnic table under the covered pier if you need to get out of the sun for a bit. Watch kids as they fish or crab for their next dinner. The wharf also features a top deck for expanded views of the harbor, including Edgartown Harbor Light. If you are just visiting the island for the day, then Edgartown is a great destination for cyclists who rent bikes in Oak Bluffs and want to travel the many bikeways of Martha’s Vineyard. It is a six-mile ride between Oak Bluffs and Edgartown, so riding the whole path may not be suitable for young children.

Katama/South Beach

Bicycle or take the #8 bus to South Beach and enjoy a “real beach” with real surf. You will find miles of beach to stroll, find sea glass and shells, or just spread out your towel and bury your feet in the sand. There are no concessions at this beach, so don’t forget to grab sandwiches and beach food at Rosewater Market or Katama General Store before you catch the bus.

Village Walkabout

Stroll through the streets of Edgartown and view the historic whaling captain’s homes, complete with widow’s walk. Although popular mythology states that these rooftop terraces were for the wives of mariners to watch their husbands sail from the harbor, perhaps for the final time, there was a more practical purpose. Built around a chimney, the widow’s walk provided rooftop access and was used to pour sand down the chimney in the event of a fire.

If you are a fan of architecture or are interested in the historical aspects of Edgartown, then the Martha’s Vineyard Preservation Trust offers a 90-minute walking tour of five of the town’s historic sites.

Edgartown Harbor Light

Edgartown Harbor Light

This lighthouse stands near the center of Edgartown and is easily accessed by foot. The original lighthouse was constructed in 1828 but was severely damaged in 1938 by a hurricane. The 45-foot iron tower that stands today was built the following year in Edgartown Harbor but now is surrounded by a barrier beach allowing visitors to see it up close. At the foot of the tower is the Children’s Memorial consisting of granite cobblestones with the engraved names of children who have passed on too soon.

Interior tours are available in 2021 and visitors can climb to the lantern room and get a unique view of Edgartown and its harbor. A lighthouse keeper is available during operating hours to answer questions and provide a brief overview of the lighthouse.

Chappaquiddick Bike Ride

Mytoi Garden Chappaquidick

Rent a couple of bicycles and take the “On-Time” ferry to Chappaquiddick Island. Visit Mytoi Japanese Garden, ride over the Dike Bridge, a.k.a. the Kennedy Car Wash, and keep riding until you see the ocean at secluded East Beach ($5 Fee). If you are looking to separate yourself from the crowds that form in the town centers, then this is a great way to do it. Concessions are limited here, with one retail outlet – The Chappy Kitchen. You can grab lunch items here, including sandwiches for the beach, or pack them ahead of time from the Katama General Store in Edgartown.

Vineyard Haven

While there are more interesting towns on the island than Vineyard Haven, also known as Tisbury, there are a few highlights to enjoy while here. If you are just coming over for the day on the Steamship Authority Ferry, then there is a good chance that your ferry will embark or disembark from Vineyard Haven. 

Go Kayaking or Stand-Up Paddleboarding

Head over to Wind’s Up, a short walk from the Steamship Authority ferry terminal where you can rent kayaks or stand-up Paddleboards for a couple of hours. Located on “the lagoon”, the water is shallow, warm, and calm. This is a great location for novices to try out one of these popular paddlesports. Guided tours are also available.

Eat Lunch at the Black Dog Tavern

While most people know The Black Dog brand for their T-Shirts and baseball caps featuring the iconic black lab, it began with a small cafe located in the center of Vineyard Haven.

Founded in 1971 by former US Air Force pilot Robert Douglas, the Black Dog was originally meant to be a year-round establishment for locals, and it still serves that purpose in the off-season. Summer though belongs to the visitors. In the early 1990s, the brand gained popularity when celebrities including President Bill Clinton were photographed while wearing the tavern’s souvenir T-shirts. Soon, Black Dog merchandise outsold the food and drink items, and with the advent of the Internet – well, the rest is history.


Menemsha Harbor

Menemsha Harbor

Step back in time to the way Martha’s Vineyard used to be. Old-timers may talk of island life before the crowds came…before celebrities and power brokers came and razed the cottages in favor of huge mansions. While those days are long gone now, Menemsha Harbor remains a holdout to that bygone era when the fishing economy was strong and provided islanders with plentiful opportunities.

The harbor is still lined with working fishing boats and modest homes, at least by Vineyard standards. Visitors can enjoy a casual dinner at Home Port, Menemsha’s only sit-down restaurant. BYOB is the theme here, so bring a bottle of wine to go along with dinner. Menemsha Galley is a take-out seafood shack for those that want to grab a basket of clams or a lobster roll and either head over to the pier or nearby Menemsha Beach (map) to catch one of the most amazing sunsets on the island.

It’s low-key on this side of the island, and Menemsha certainly puts the chill in Chilmark.


Aquinnah Cliffs and Moshup Beach

Aquinnah Cliffs

Photo by Kindra Clineff. Courtesy of MA Office of Travel & Tourism, CC BY-ND 2.0

Once known as Gay Head, the town is now normally referred to by its native Wampanoag name of Aquinnah. The all the characteristics of Aquinnah, the 150-foot cliffs that stand tall along the southwest corner of Martha’s Vineyard are the most outstanding. While the cliffs themselves and the beach below are off-limits in order to protect them from excessive erosion, Moshup Beach (map) is nearby and gives beachgoers a fairly close-up view of this unique island feature.

Did I say that the cliffs were the most unique feature of Moshup Beach? I forgot to mention that the far side of the beach nearest to the Aquinnah Cliffs is clothing optional, and that certainly could divert your attention and make for an even more interesting story when you get back home. Just bring the sunblock and stay away from the Instagram selfies while at this end of the beach.

As usual, parking is the biggest issue when visiting Cape Cod and Martha’s Vineyard. At Moshup, there is a parking lot that can be accessed via Moshup Trail, but be sure to get there early as the lot will fill up during the summer season. The fee is $15.00. Your best bet when traveling around Martha’s Vineyard is to purchase a one, three, or seven-day bus pass through the Vineyard Transit Authority. This will get you just about anywhere on the island without the very real hassle of trying to park your vehicle.

Knockabout Oak Bluffs Audio Tour

Take a self-paced walk through the island’s most popular town. Includes all audio files streamed directly to your smartphone. No apps, no accounts, no passwords to remember. Super easy.

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