Delving Deeper into Edgartown

In 1692, Reverend Thomas Mayhew, Jr. brought group of families to begin to colonize a part of the island, after his father Thomas Mayhew purchased it. The town’s current name is a tribute to Edgar, the son of James II of England, who died at the age of three in 1671. In the 1800s Edgartown began hosting ships from all across the world and captains would built mansions for their families – generally with widow’s walks that are found on the top floor and overlook the harbor. The tiny town was able to make fortunes through this port – and is now generally known for its tourism.





Edgartown has several boutique shops for visitors to explore, which are mostly found on Main Street. Slate is a new store on the island, and there you can find gorgeous nautical themed clothing. At In The Pink find classic, preppy Lily Pulitzer prints in dresses, pants, shirts, and skirts. Edgar is perfect shopping for those looking for high-end Vineyard clothing and golden swan-shaped pool floats. Backwater Trading Company has East Wharf Bags, an eco-friendly company considering all their bags are made entirely from recycled sails. They come in all different sizes, from wristlets and wine totes to beach bags.




Ice Cream

At the end of Main Street in Edgartown, you can watch the boats coming in to shore. Right on the water is the Ice Cream Candy Bazaar, where you can grab a little basket and pick out your favorite guilty pleasure, whether it’s Smarties, Twizzlers or chocolate anything. It’s also a great place to watch the sunset over Chappaquiddick. 


Mad Max

Next to the Ice Cream Candy Bazaar, you can hop on the Mad Max, which is a state-of-the-art catamaran. It sails daily at 2 p.m. and 6 p.m. and can be rented for private sails for parties up to 49 people. The boat sails past the Edgartown Lighthouse, and one course ravels along Chappaquiddick shores, and another goes past the colorful towns of Oak Bluffs and Vineyard Haven.


Catboat Charters

This could couldn’t be a true in-depth look into Edgartown without mentioning “The Tigress” Catboat charter sailboat. If you have spent anytime on the Edgartown the you have most likely seen the characteristic American Flag sail cruising through the harbor. Captain Curt offers a variety of cruise destinations and lengths, so be sure to check out his website here (and for more beautiful shots, check out his Instagram too).


Edgartown Lighthouse

The Edgartown Lighthouse is probably one of the sights you think of, when you think Martha’s Vineyard. Originally it was built on a standalone island, before the sands eventually connected it to the greater land of the town. It is available for private occasions such as weddings, and tour times of the lighthouse can be found here. Plenty of dogs can be spotted running around with their owners on Lighthouse beach, and splashing in the calm waters of the bay.





Henry’s looks over the Edgartown Lighthouse and harbor, and it only a short walk away from the beach. Located in the historical Harbor View Hotel. Henry’s is the more casual of the two restaurants located in the hotel. It’s a gastro-pub with an Edgartown flair.  It has a Tapas-ispired menu with small plates and full-size entrees alike. Here, you can buy one of their signature cocktails, while enjoying one of the best views in town. The best thing on the menu? The lobster tacos.




Katama Airfield

It’s only a short bike-ride to the Katama Airfield, located outside the town’s main drag. It is the largest grass airport in the United States, and you can get a great view of planes taking off and landing. There, you can eat at their enormously popular Right Fork Diner and experience some classic favorites like burgers, shakes and fries and enjoy the planes. If the line is too long, or you’re looking for a quick bite they have a snack bar where you can order the best milkshakes on island. I swear. There are bi-plane rides that satisfy thrill-seekers and view-enjoyers alike. You can go on a trick ride, where the plane barrel rolls, twists and turns or choose a specific route and see some parts of the island from the skies.




South Beach

South Beach is just down the road from the Katama Airfield, and is one of the most popular destinations on island. It extends three miles and has extensive parking lots for those always worried about double parking, illegal parking, and of course, the parallel park. On one side, there is a large salt water pond, which works great for those with little kids who are just learning to swim. On the other side is beach with surf, which works best for more experienced swimmers.south-beach

Oak Bluffs: Town Profile

Town Profile: Oak Bluffs




Oak Bluffs is one of the hottest towns in Massachusetts during the summertime, and one of Martha’s Vineyard’s most popular hubs. It’s historic yet modern, quiet but loud – it manages to vary depending on how exactly you want your visit to be. It’s super easy to walk around OB since it is so compact, as Vineyard towns tend to be. So spending a day in Oak Bluffs is easy and fun. Here are a few of the activities and places to see on your visit.


Flying Horses Carousel

The Flying Horses Carousel is open from 10AM-10PM in the summertime. It boats the title of oldest carousel in the United States and was first operated in 1876 on Coney Island in NYC. It is also recognized as a historical landmark. To me, it’s a childhood memory. It wasn’t until 1884 when the carousel was relocated to Oak Bluffs. The horses still have their original eyes, but their original horsehair manes have been replaced. As you go around the carousel, admire the original artwork surrounding you and try to capture as many brass rings as you can – because the last one is the brass ring which gives you a free ride! Otherwise rides are $1.50 for a single ride.



Martha’s Vineyard Camp-Meeting Association Cottage Museum and Gift Shop

Oak Bluffs is known for its vibrant (non-edible) gingerbread houses, and traditionally decorated with lanterns for the annual Illumination Night. However, the cottage museum is the only gingerbread house that the public is invited to see. It’s a great opportunity to see the 1800s furnishings that most Vineyard houses would have had during those years. The tour also provides a history of the campground and its background. The gift shop sells jewelry, postcards as well as the aforementioned lanterns. The hours of operation are Monday-Saturday 10AM – 4:30PM.




Pecoy Point Preserve

Pond shores, sloping grasslands, salt marshes and a freshwater pond are some of what you’ll find at the Pecoy Point Preserve. Located near Oak Bluffs, this all-natural land serves as an escape from the suburban. It’s a perfect place for outside activities such as hiking, mountain-biking, horseback-riding, dog-walking, fishing, and kayaking.


Ocean Park

You’ve probably seen a picture or twenty of the big white gazebo located in Ocean Park, the heart of Oak Bluffs. It’s a beautiful little park that has views of some of the gingerbread houses, and Oak Bluffs Town Beach which overlooks the sea. Here you can fly a kite, or watch the fountain or play with your dog. The gazebo is especially beautiful at night when it’s lit up.




Circuit Avenue

Circuit Avenue offers quite the potpourri of shops to the ordinary traveler. It is also flush with bars, restaurants, ice cream stores and great people watching. Some places you should stop on Circuit Ave include:


Johnny Cupcakes

While unfortunately it is not a bakery, Johnny Cupcakes is a fun place to find graphic tees. They’re sold out of industrial size refrigerators, with Martha’s Vineyard specific designs, even though it’s an international brand. Think skull and bones prints, but with cupcakes. Nothing better.





Every piece of jewelry in this store is made from people on island. A nod to the Wampanoag tribe on island, a solid amount of the jewelry is made from wampum. Martha’s Vineyard shaped necklaces and accessories can be found here.
Slip Seventy-Seven

This store is a casual contemporary clothing store, for those looking for something more relaxing to lounge in, compared to some of the more high-end retailers on the island. Slip77 in Oak Bluffs is its flagship store, and therefore draws its name from its location. The store is near the boat slips in the harbor, as well as the revolutionary year of ’77.


Good Dog Goods

Good Dog Goods is the cutest little shop for dogs and dog lovers everywhere. Decorated with dog-themed paraphernalia, this shop offers mugs, pillows, frames amongst other things with almost every breed of dog imaginable. They also have a cute little bakery in the back with delightful biscuits shaped like lighthouses to whales. I do not recommend eating (although tempting) because they’re only for dogs.




Ryan Family Amusements

An old-timey arcade located in the middle of circuit avenue, where you can win big with their various games. A perfect rainy day activity to tire out your kids. They have the traditional skee ball machines, hunting simulators and toy grabbers for those who think they’re especially lucky.




Oak Bluffs Town Beach

The Oak Bluffs Town Beach is located just a quick walk from Ocean Park and where the Steamship Authority’s dock in town. It is a clean beach with calm waters whip lap the shore very gently. Here you can lounge, play and swim – only a walk away from several in-town restaurants.





Giordano’s has been a popular hub in Oak Bluffs since the 1930s. It’s a four-generation long family restaurant with, as voted by Martha’s Vineyard Magazine for several years in a row, the best pizza on island. They also have a convenient take-out pizza window, and a seafood window for those who are on the go – or want to sit in Ocean Park instead of the restaurant.



-Isabel Getz