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.
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.
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.
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).
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.
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 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.