Martha’s Vineyard: The Magical Island

I visited Martha’s Vineyard a few times as a child, and I’ve finally returned as an adult! A little island escape, complete with ferry rides, colorful gingerbread cottages, peaceful beach mornings, and approximately one million seafood options. I drove down to Falmouth, grabbed the shuttle to the ferry, and 45 sunny minutes later I arrived at the Vineyard!

The Town:

Oak Bluffs (one of the most historically interesting places on Martha’s Vineyard)

• The town became known as Cottage City in 1880 and officially became Oak Bluffs in 1907.

• If you’re staying near the coast, it’s a very walkable town with plenty of shops, restaurants, and activities.

• Home to the famous “gingerbread” cottages (more on that below).

• By the early 20th century, it had become a major summer destination for Black families, professionals, artists, and intellectuals at a time when segregation and discrimination made many other vacation destinations inaccessible.

Where to eat

Breakfast:

• The Daily Brew:
  Not on the island, but a great first stop before heading toward the ferry. Coffee + breakfast + road trip = the right way to start. Be sure to give yourself extra time though, the lines get long as it’s one of the only places near the ferry’s parking lot!

• Biscuits:
  A popular breakfast spot, but there’s a catch: the lines get VERY long. Go early or prepare to wait!

Lunch:

• Highlands General:
  A casual Oak Bluffs spot that’s perfect for an easy lunch between exploring (also open for breakfast!).

• Fish MV:
  A laid-back seafood stop in Vineyard Haven with a fun coastal vibe and delicious drinks.

• Lookout Tavern:
  If you’ve been wondering where to find the biggest lobster roll, it’s here! If you’re going to eat a lobster roll on Martha’s Vineyard, you might as well go big.

Dinner:

• Nancy’s:
  A classic Oak Bluffs waterfront stop. Grab a delicious dinner (seafood with Mediterranean options), enjoy the harbor views, and settle into island mode. Also a great lunch option.

• The Harbor View Hotel:

  For a slightly fancier night, Bettini at the Harbor View Hotel offers contemporary American cuisine, coastal-chic vibes, and gorgeous views of Edgartown Harbor.

Dessert:

There are a TON of ice cream spots within a 50 ft radius but this is where I tried:

• Nauti Cow:
  Because no beach vacation is complete without ice cream. Bonus points: they have great dairy-free options, too. Lactose-intolerant people rejoice!

Things to do

• Start the morning with a polar bear plunge:
  if you're an early riser—or just slightly insane—there's a 7:30 a.m. water aerobics group at Inkwell Beach, which is like a daily polar bear plunge with a workout attached. Count me out, but it’s a “thing” there so definitely worth mentioning.

• Beach yoga at Inkwell Beach:
  Morning yoga by the water at Inkwell was exactly the kind of peaceful island activity I needed. Inkwell Beach is also one of Oak Bluffs’ most iconic beaches, with a long history and cultural significance to the Black community.

• Tour the Gingerbread Houses:
  One of my favorite stops was the Campground, home to the adorable, candy-colored “gingerbread houses.” The cottages are actually part of the historic Martha’s Vineyard Camp Meeting Association, and you can take a guided tour for only $15. Highly recommend! Plus the cover charge allows the organization to keep running and all the sweet guides are volunteers.

• Ride a 150-year-old carousel:
  Oak Bluffs is also home to the Flying Horses Carousel, which celebrated its 150th birthday in 2026! Built in 1876, it’s the oldest operating platform carousel in the country, and yes, you can still try to grab the famous brass ring. I’ve also tried this and it’s infuriating as much as it’s entertaining.

• Explore the island’s history:
  The Martha’s Vineyard Museum in Vineyard Haven is a great rainy-day stop, with exhibits covering the island’s maritime history, culture, lighthouses, and stories. In a previous life, the building was a Marine hospital through WWII and then was a summer camp before being converted into a museum in 2011.

• Island Alpaca Farm:

  Yes, there are alpacas on Martha’s Vineyard! Island Alpaca is a working farm in Oak Bluffs with a herd of more than 50 alpacas. You can wander around the pastures, meet the animals (AND PET THEM!), and browse the farm shop filled with alpaca-fiber goods.

• Jaws Bridge:

  The American Legion Memorial Bridge connects Oak Bluffs and Edgartown and was featured in the 1975 movie. It’s become a classic Martha’s Vineyard photo stop—and a famous spot for the traditional bridge jump. I’m terrified of jumping from high heights, but teenage me took the plunge anyway!

Shops

• Jubilee (Oak Bluffs):
  A Black owned boutique with gorgeous and unique finds of clothing and accessories! I love that they not only have their own designs, but also stock pieces from independent designers.

• Rainy Day (Vineyard Haven):
  Rainy Day is a particularly fun browse when you need a break from the beach. It has a big mix of home goods, cards, toys, and other fun misc items.

• Main Street (Vineyard Haven):

  Literally the “main street” of the town, have fun popping in and out of all the shops! Aside from Rainy Day, there’s an adorable book store with gorgeous cards and a store cat named Bookmark as well as a few vintage/second hand shops. Be sure to stop by the locally-famous Murdick's Fudge.

• Circuit Avenue (Oak Bluffs):

  The main street of the town of Oak Bluffs, this is where you’ll find Jubilee (listed above) and many other adorable shops, like C’est La Vie, Third World Trading Co, and the original Black Dog.

Pro tip for traveling to the Vineyard: If you’re planning to visit during the season (Memorial Day through Labor Day), be sure to book accommodations as early as you can since many regulars scoop up their go-to spots a YEAR in advance! The ferry, on the other hand, doesn’t need to be booked that far advance for passengers traveling without a car. You can book online, have the tickets on your phone, and they’re good for 2 years!

Martha’s Vineyard is truly a little gem of an island with a magical coastal vibe and rich history. I love that each town has it’s own distinct personality, but (fun fact) share ONE high school so graduation is when they all come together! Even if you only go as a day trip, I promise it is well worth it.

Samantha Shammas, Author

A true travel enthusiast, Samantha has been going around the globe her entire life and has visited over 40 countries and counting. With a lust to wander, she’s always excited to visit new places and soak in inspiration for her artwork.