Things To Do
Nancy's Restaurant
29 Lake Ave Oak Bluffs, MA- Located right on the marina in Oak Bluffs, Nancy's is a great place for a relaxing lunch or casual dinner on the water. Try the fried shrimp or the baked cod! Also check out Donovan's is located right next to Nancy's and has the best frozen drinks on the Island (or in the country). He's famous for the dirty bananas but he also makes a mean pineapple lime drink.
Giordano's Restaurant, Inc
Located in the middle of Oak Bluffs, Giordano's is a great neighborhood pizza and Italian restaurant
Bangkok Cuisine
A little off the beaten path in Oak Bluffs, Bangkok Cuisine is a great alternative to all of the lobster rolls and seafood if you've had your fill.
Lookout Tavern
As the name suggests, the lookout looks over the water towards where the ferry docks. This is a great place for seafood and sushi.
Biscuits
Biscuits is a casual breakfast and brunch spot located on the other side of the Oak Bluffs marina. As the name might suggest, they're known for their biscuits and biscuit sandwiches.
Sand Bar & Grille
Sand bar is exactly how the name suggests- located right off the marina in Oak Bluffs- down the pier from Nancy's and Donovans. It's a great outdoor bar and restaurant that serves sushi as well as other seafood and American fare.
Offshore Ale Co
Microbrewery not far from circuit ave in Oaks Bluffs with standard pub fare and a rustic vibe. Had one of the best takes on blueberry beer that we have tried to date!
Flying Horses Carousel
The flying horses is an Oak Bluffs staple. Najah used to frequent the flying horses every year during her summer trips to the Island and she would compete with Saarah to see who could get the most rings on their fingers at one time (you'll have to go there to know what I mean by this)!
Inkwell Beach
The inkwell is Oak Bluff's beach which is within walking distance of the Oak Bluffs Ferry as well as the center of town. It is a relatively small beach but super convenient. There's also a famous movie with it's name sake featuring Larenz Tate
Joseph Sylvia State Beach
Down the road from Inkwell beach between Oaks Bluffs and Edgartown - features a bit quieter fare if you're not too squeamish about parking on the side of the highway. This dot will get you pretty close to the spot where we took our engagement photos that are on the beach!
Chartered Fishing Boats
For those so inclined, you can charter a fishing boat to go out for a morning or afternoon sail to see what bites! Proper credentials to fish and bait and tackle are included in the reservation cost!
Circuit Avenue
The main strip in the Oak's Bluffs District. If you feel like shopping, eating or just walking around the town, Circuit Ave is the place to be. Here you'll find an ice cream shop every two steps, an arcade, lots of restaurants, and cute little shops
Among the Flowers Cafe
This is a cute little restaurant right in the heart of Edgartown that's perfect for breakfast or brunch.
Bad Martha Farmers Brewery
Just outside core Edgartown is a cozy microbrewery next door to a lush nursery. Good brews, great snacks, often had entertainment in the evenings!
The Seafood Shanty
Located right on the marina in Edgartown, the Seafood Shanty is a favorite of ours for great seafood, sushi, and cocktails, especially at sunset.
Atlantic Restaurant
Atlantic is located on the other side of the marina and has a great back patio area with glass fire pits- if it gets a bit chilly at night we would definitely recommend stopping here for tasty food and drink as you cozy up to the fire. Also turns into a club at night.
Behind the Bookstore
Behind the bookstore is small cafe which is literally behind a bookstore in the middle of downtown Edgartown. Great for health salads and artisinal cocktails
Mad Martha's Edgartown
Located in all three major towns on the island, this ice cream shop is known for its HUGE scoops- one scoop is more than enough to share between two!
Shopping in Edgartown!
Edgartown has tons of boutiques from clothing to art to jewelry. A few of Jen's favorites: o Nell, 20 Main St o Slate, 11 N Summer St o Stefanie Wolf Design, 12 N Water St
Mad Max Sailing Adventures
Great for a sail around the island during the day or at sunset. This boat also allows you to bring your own food and drink.
Gay Head Lighthouse
If you have some extra time on the Island and want to explore a bit, Gay Head is definitely worth a trip. The Gay Head Lighthouse is a historic lighthouse located on the westernmost tip of the Island.
Menemsha Public Beach
Menemsha has the most beautiful sunsets on the island and I would recommend the drive up just for that! We love bringing a bottle of wine and a blanket, grabbing some seafood from one of the many take-out restaurant in the area and posting up at the beach for the sunset.