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If you’ve ever visited or lived on the east coast, specifically New England, chances are you have spent time on or heard about the lovely island of Martha’s Vineyard. This island is located about forty-five minutes via ferry off the coast of Cape Cod, Massachusetts. Honestly, as a kid, I thought Martha Stewart owned the island and that there were actually wine vineyards on this island. Sadly, both are false.
Martha’s Vineyard may be a small island, home to about 17,000 year-round residents, but it is certainly a hot spot to visit in the summer months. June through September are the best times to visit but are technically in busy season. During this time, the island population reaches up to 200,000 people!
While we’re at it, let’s be friends on Instagram and Tiktok!
When visiting Martha’s Vineyard, you are guaranteed to experience beautiful beaches, delicious restaurants, and outdoor activities. It also has hot days with cool nights and a diverse pool of travelers all looking for a little escape from their own realities.
Some visitors come to the island just for the day, but a weekend or longer would be the most ideal time frame in order to hit every must-see destination on the island. In fact, Martha’s Vineyard would be the perfect spot for a summer weekend getaway. I spent about 4 days here and wish I had longer!
Traveling to Martha’s Vineyard will require taking a ferry from one of the terminals listed. The ferry will then bring you into one of two terminals on the island: Oak Bluffs or Vineyard Haven. When traveling with a vehicle, car reservations must be made months in advance for trips taken during the busy summer months. Guests without cars should purchase tickets per individual passenger before arriving at the ferry.
Martha’s Vineyard is made up of six towns: Aquinnah, Chilmark, Edgartown, Oak Bluffs, Tisbury, and West Tisbury.
Each town has something special to offer and there truly is something for everyone. Whether you are experiencing Martha’s Vineyard with a group of friends, a significant other, or family members, get your planners ready and take a look at this bucket list of 25 things to do in Martha’s Vineyard during your weekend stay.
While we’re at it, let’s be friends on Instagram! Also, you may want to check out this reel I made for things to do on Martha’s Vineyard in short video form.
➡️ See more posts about 1 Visit the gingerbread cottages in Oak Bluffs
1 – Visit the gingerbread cottages in Oak Bluffs
First on the list is to take part in one of the most well-known attractions on Martha’s Vineyard. The vibrant “gingerbread cottages” in Oak Bluffs! The 318 gingerbread homes spanning a few blocks are painted with every color under the rainbow and have cozy front porches with quaint furniture and small balconies. The story behind the gingerbread houses originates way back in 1835 when a group of local Methodists used to attend religious camp meetings in Oak Bluffs.
At the time, those who traveled to the island to join the meetings would pitch canvas tents for their overnight stays, which eventually led to the need for a more permanent home on the island for these visits.
The construction of the cottages began years later in 1864 and was influenced by a variety of common architectural norms at the time. The adorable homes look like they came out of a fairy tale – or maybe a game of Candy Land – and are certainly a must-see when spending time in Oak Bluffs. I got lucky enough to stay in my friend, Alex in Wanderland’s beautiful Oak Bluffs home! Check out her blog for a tour of the inside of her house.
➡️ See more posts about 2 Eat ice cream at Mad Marthas
2 – Eat ice cream at Mad Martha’s
Mad Martha’s is one of the most popular ice cream names on the island and has three locations between Edgartown, Oak Bluffs, and Vineyard Haven. Satisfy your sweet tooth with a visit to Mad Martha’s and enjoy one of their delicious homemade flavors.
➡️ See more posts about 3 Bike the island
3 – Bike the island
A perfect way to spend one day of the weekend could be touring around the island on bikes and stopping in each of the towns along the way.
All-Star Martha’s Vineyard Bike Rentals is right next to the Oak Bluffs ferry and Martha’s Bike Rentals & Sales is right next to the Vineyard Haven ferry. The six-mile bike ride from Oak Bluffs to Edgartown is known for being a gorgeous and manageable ride, including riding over Jaws Bridge! Another great area to ride is East Chop. You can bike along the water and see beautiful homes and the East Chop Lighthouse.
➡️ See more posts about 4 Jump off Jaws Bridge or watch a screening
4 – Jump off Jaws Bridge or watch a screening
Spielberg’s famous 1975 shark attack movie, Jaws, was filmed in Martha’s Vineyard. This may be why the American Legion Memorial Bridge already looks familiar. This is also what gave the bridge its more recognized name of “Jaws Bridge”. No need to fear, the shark attack only occurred in the fictional movie.
Jaws Bridge is a safe bridge that has become known for being the perfect bridge for adrenaline-seeking bridge jumpers. The bridge sits about 12-15 feet above the water, making it a safe jumping height for both children and adults. Park your car along the side of Beach Road in Edgartown and make your way to the line of eager jumpers waiting their turn at the top of the bridge.
Be sure to plan your jumping around high tide, because the water down below is not very deep. Oh, and do not worry about the “no jumping” signs next to the bridge, bridge jumping is an island-accepted activity.
Want more Jaws in your life? Watch a screening of the movie at the Capawok Theatre or The Strand every Friday night in the summertime!
➡️ See more posts about 5 Tour the Gay Head Lighthouse and the Aquinnah Cliffs
5 – Tour the Gay Head Lighthouse and the Aquinnah Cliffs
As you may have guessed, Martha’s Vineyard has quite a few lighthouses, and Gay Head Lighthouse in Aquinnah is one you should visit. You can take a formal tour of the lighthouse and learn all its history dating back to 1796 or just walk around yourself. This is a beautiful day trip to take if you’re staying further down the island.
While you’re at it, visit the Aquinnah Cliffs, a mile-long expanse of clay cliffs by the edge of the town of Aquinnah. It’s a beautiful place to go for a day trip and enjoy the western portion of Martha’s Vineyard.
➡️ See more posts about 6 Purchase farmfresh groceries from Morning Glory Farm
6 – Purchase farm-fresh groceries from Morning Glory Farm
Morning Glory Farm, located in Edgartown, is a popular farm stand on the island selling a wide selection of fresh produce, baked goods, and premade meals. The family-run farm began in 1975 and now grows about sixty-five acres of fruits and vegetables on the island.
If you want to cook a meal or two at your rental home, Morning Glory Farm would be the perfect place to purchase veggies to grill for dinner. Now for the baked goods. While you can’t go wrong with any of the options at the farm stand, the zucchini bread is definitely a fan favorite and should be tried even if you do not think you are a zucchini bread lover. Morning Glory Farm does it best. Be sure to pick up a zucchini loaf and enjoy a slice toasted with butter as part of your breakfast.
➡️ See more posts about 7 Enjoy the many different beaches on the island
7 – Enjoy the many different beaches on the island
While you are on the island for the weekend, you must make time to hit the beautiful New England beaches. There are many incredible beaches on Martha’s Vineyard! South Beach is the beach for you if you enjoy big waves when you swim. South Beach is a public beach located in Edgartown.
Surfing, body surfing, boogie boarding, and swimming are all allowed on this beach, so it is perfect for any group that enjoys splashing around in the water. Grab your sunscreen, towels, chairs, beach accessories, and a cooler full of snacks and drinks because once you arrive at South Beach for the day, you will not want to move from your spot.
Another great beach is Norton Point Beach. It’s one of only two beaches on Martha’s Vineyard that allows cars to drive on the beach. Load up all your goodies into the car and head to Norton Point early to enjoy a Saturday beach day. Be sure to purchase a pass ahead of time to gain access to the beach and follow proper beach driving rules, like deflating tires, before entering.
Other great beaches include Lambert’s Cove, State Beach, Moshup Beach, and Katama Beach.
➡️ See more posts about 8 Catch rings at the Flying Horse Carousel
8 – Catch rings at the Flying Horse Carousel
No matter what your age, you will enjoy a ride on the historic Flying Horses Carousel in Oak Bluffs. Built-in 1876, the Flying Horses Carousel is the nation’s oldest platform carousel.
The carousel was once an attraction on Coney Island but was moved to Oak Bluffs which has been its permanent home since 1884. The carousel is a work of art itself, spinning around its brightly painted horses whose manes and tails contain real horsehair.
As riders enjoy the music and tempo of the carousel, they can also reach up from their horse (only on the outer row) to grab a three-inch silver ring from a ring dispenser in one section of the room. Most of the rings dispensed throughout the ride will be silver, except for the one gold ring that comes out at some point during the ride. The lucky winner who snags the gold ring earns themselves a free ride on the carousel.
➡️ See more posts about 9 Enjoy dessert from Back Door Donuts
9 – Enjoy dessert from Back Door Donuts
Have you ever ordered a donut from the back door of a bakery? Well, at Back Door Donuts that is the norm during the store’s nighttime hours. Back Door Donuts, located in Oak Bluffs, offers a variety of delicious donuts fresh out of the oven.
Stick with the donut basics by ordering a Boston Creme or Chocolate Glazed, but if you’re feeling bold, the Maple Bacon will be a pleasant surprise. While Back Door Donuts is known for its donuts, the Apple Fritter is also a must-order and is massive enough to be shared between two people.
The store’s normal indoor bakery is open from 8 am to 5 pm if you find yourself craving a donut during the day, but the back door is where you want to get your treats from 7 pm to 1 am specifically on the weekends. Be prepared to stand in a long line with other eager donut eaters, but it will certainly be worth the wait.
➡️ See more posts about 10 Stroll along the walking trails
10 – Stroll along the walking trails
Take a break from the large array of treats on Martha’s Vineyard and get some exercise by strolling along with one of the scenic walking trails on the island. Felix Neck Wildlife Sanctuary, Caroline Tuthill Preserve, and Long Point Wildlife Refuge all offer various kinds of hiking trails and walking trails.
➡️ See more posts about 11 Eat lobster rolls from Larsens Fish Market
11 – Eat lobster rolls from Larsen’s Fish Market
While in Martha’s Vineyard, it is crucial that you get your taste of fresh seafood. Larsen’s Fish Market in Chilmark is one of the best places to visit for fresh seafood. Enjoy a Larsen’s lobster roll, stuffed scallops, oysters, crab cakes, or essentially any other fish commonly sold at a fish market. The market is right along the Menemsha Basin, so you can enjoy your seafood while overlooking the fishing boats that obtained the fish, right in front of you.
➡️ See more posts about 12 Shop in downtown Edgartown or Vineyard Haven
12 – Shop in downtown Edgartown or Vineyard Haven
Edgartown is the best place for shopping in Martha’s Vineyard because of the many quaint stores lined up along its downtown area. There are plenty of shops to visit in Edgartown – from women’s boutiques to art galleries, candy stores, home decor shops, men’s clothing stores, book stores, and souvenir shops.
Vineyard Haven also has a great little main street area with cute shops and restaurants that are definitely worth checking out during your weekend getaway
➡️ See more posts about 13 Order fudge from Murdicks
13 – Order fudge from Murdick’s
Another island non-negotiable is to make a visit to Murdick’s Fudge in Oak Bluffs and Edgartown. Murdick’s offers over twenty-five different flavors of fudge that you may even be able to see employees making when you walk in the store at the right time. If your travel logistics allow for it, it could be a good idea to bring a little extra fudge back as a gift to someone at home.
➡️ See more posts about 14 Enjoy the nightlife and enjoy a sunset or two
14 – Enjoy the nightlife and enjoy a sunset or two
If you are wanting a night out with drinks, music, and dancing while in Martha’s Vineyard, there are definitely some cool places to check out. The Cardboard Box, The Ritz, The Sand Bar & Grille, and The Newes from America are a few places that come to life during the nighttime when drinks are flowing and music is playing.
Want to watch a beautiful sunset? Head to the Harbor View Hotel where you’ll get to watch the sunset over the Edgartown Harbor and see the lighthouse in the distance.
➡️ See more posts about 15 Sail in the Vineyard Sound
15 – Sail in the Vineyard Sound
There are plenty of boating opportunities available on Martha’s Vineyard! This could be a relaxing activity to include on your weekend itinerary. These sails will take passengers around the Vineyard Sound. This is the stretch of the Atlantic Ocean that separates the Elizabeth Islands and the southwestern edge of Cape Cod from Martha’s Vineyard. Sailing charter companies, like Catboat Charters, Island Sailing Tours, and Sail the Vineyard, offer sailing tours daily all throughout the summer months.
➡️ See more posts about 16 Go golfing on a public course
16 – Go golfing on a public course
If you love to golf, then take advantage of some of the gorgeous golf courses in Martha’s Vineyard. There are three golf courses open to the public that would be most convenient for anyone visiting for the weekend. These courses are Mink Meadows Golf Club; Farm Neck Golf Club; and Royal and Ancient Chappaquiddick Links. Each course has something special to offer and clubs can be rented if you did not pack yours on your trip.
➡️ See more posts about 17 Eat at one of Marthas Vineyards best restaurants
17 – Eat at one of Martha’s Vineyards’ best restaurants
There are so many great restaurants to choose from when dining out on Martha’s Vineyard. Some great ones to try in Edgartown are Port Hunter, Sharky’s Cantina, or Chesca’s Restaurant. Edgartown is one of the more expensive areas on the island, so the restaurants tend to follow suit.
In Oak Bluffs, try out Red Cat Kitchen, Nancy’s Restaurant, a giant seafood restaurant overlooking the Oak Bluffs Harbor. Another great restaurant on the island according to my friend Alex in Wanderland is State Road. If you’re craving chowder, try Martha’s Vineyard Chowder Company. For breakfast, I highly recommend going to Art Cliff Diner or Biscuits in Oak Bluffs!
➡️ See more posts about 18 Tour Marthas Vineyard Museum
18 – Tour Martha’s Vineyard Museum
If you get a rainy day while on Martha’s Vineyard and need something to do inside, take a trip to the Martha’s Vineyard Museum in Tisbury. Founded in 1922, the museum teaches all about the history of the island and the diverse people who make up its origins.
➡️ See more posts about 19 Visit Chappaquiddick Island
19 – Visit Chappaquiddick Island
Chappaquiddick or “Chappy” is an eighteen-square-foot island on Martha’s Vineyard that’s worth checking out during your weekend trip for a little quiet time.
Travelers can get to Chappy using a small ferry carrying only a few cars simultaneously across a short channel on the Edgartown Harbor. The draw to Chappy is its privacy and quietness. This may not always feel attainable among bustling tourists. Chappaquiddick is excellent for sunbathing, quiet walking paths, and plenty of nature. While you’re here, you might also want to opt to check out the Cap Poge Wildlife Refuge, a protected nature area with 14 miles of sand trails & beach access. There’s also a small Japanese Garde, Mytoi, popular among visitors.
➡️ See more posts about 20 Drink at some brewpubs
20 – Drink at some brewpubs
Despite its name, Martha’s Vineyard does not have any wineries on the island. It does, however, have a couple of breweries, including Offshore Ale Company. This brewpub in Oak Bluffs offers a variety of IPAs on tap. There is also a full food menu with classic bar bites that can be enjoyed in Offshore Ale Company’s indoor dining or patio dining set. Another great option is Bad Martha!
➡️ See more posts about 21 Visit the Island Alpaca Farm
21 – Visit the Island Alpaca Farm
Want to try something unique? Why not visit the island’s alpaca farm. This is a working farm that sells alpacas, boards them, and provides education. You can visit daily to learn more about alpacas. And take a self-guided walking tour of the farm. They also have an informative video presentation to learn more about alpacas and the local farm! It’s $5 per person to visit and is a great place to bring your family or friends!
➡️ See more posts about 22 Look out for celebrities
22 – Look out for celebrities
Martha’s Vineyard is known to be a vacation destination for a few celebrities! This includes people like Oprah Winfrey, Larry David, and Bill Murray. But your most likely run-in would be former President Barack Obama and former First Lady Michelle Obama. They own a stunning mansion in Edgartown. If you see a line of secret service vehicles traveling on the island, there is a chance it could be the Obama family.
➡️ See more posts about 23 Play tennis
23 – Play tennis
Tennis is a lovely sport to enjoy in the summer months and is a popular sport to play on Martha’s Vineyard. There are various courts across the island open to the public. Pack your racquets and balls and get some exercise on the court.
➡️ See more posts about 24 Visit a cute cafe or coffee shop
24 – Visit a cute cafe or coffee shop
If you want to have a slower morning or want to grab something quickly, try out one of the best coffee shops on the island. I recommend Among the Flowers cafe for their amazing homemade breakfast. Mocha Motts is great for its fresh coffee and eclectic menu.
➡️ See more posts about 25 Try yoga on the island
25 – Try yoga on the island
Try yoga on Martha’s Vineyard if you need some calmness or just want to get a workout in. I recommend visiting Yoga Haven, Martha’s Vineyard Yoga Barn, or Yoga on the Vine in Edgartown.
Overall, Martha’s Vineyard is the perfect destination for a summer weekend getaway. It will be a picturesque New England island vacation away from any stresses you may have left behind on the mainland. Be warned, you may even be tempted to extend your trip!
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