Known for its wings and lobster plate specials, Coop's is our favorite wing place on the island! With it's beautiful view of OB harbor and casual vibe with plastic plates and cups it's a nice break from the other restaurants on the island!

Fun fact: the owner Petey loves to sneak Stella bacon and other goodies from the kitchen :)

If you are arriving in the OB port, the first place you will see pulling in that's always packed is Lookout Restaurant! Known for it's more bar-like atmosphere and the Island's best Lobster rolls, Lookout restaurant is always a good time with a wide variety of food items on the menu!

Famous for it's donuts and legendary apple fritters, Back door donuts got it's name for serving hot and fresh fritters and donuts late at night during "after hours" in the parking lot behind the store. Before it had a reputation, you only knew about it from word of mouth, it was the Island's little secret! Over the years it has become very popular and commercialized and people travel to the Vineyard specifically for Back Door!

You can't travel to Martha's Vineyard without paying a visit to the Gingerbread Houses in Trinity Park. These summer cottages are known for their array of strikingly beautiful colors, and playful house patterns. Enjoy a nice walk through some of the vineyard's richest history. These homes used to be a campground for Methodists who would put up tents for retreats, now they are single family homes that are frequently photographed and visited by tourists around the world!

Another Martha's Vineyard Staple located in the heart of OB , The Flying Horses Carousel is the oldest operating platform carousel in the United States! Although most carousels are advertised for kids, this carousel is enjoyed by both adults and kids and during the ride, you are encouraged to try and grab the golden ring! It's competitive but fun and a must to do once!

Circuit Ave is a busy strip that is fun to walk up and down. Their are lots of shops, restaurants and sweet shops such as ice cream stores and Murdick's fudge!

Biscuit's is an OB favorite when it comes to breakfast! They have all the normal breakfast items and then some! Only problem is they fill up quickly and usually have lines of people trying to grab a table!

Located on the hustle and bustle of circuit Ave, TigerHawk and co is a sandwich shop known for it's creative twist on sandwiches for all types of consumers that have option for both meat eaters, plant based eaters!

Although we don't drink coffee, our guests tell us that Mocha Motts has the best coffee, cafe drinks and light bites!

If you ever look up Martha's Vineyard and who lives their you may notice that many of your favorite African American actors, celebrities, and politicians own homes or vacation their every summer and that is no coincidence. Martha's Vineyard was the only place for a long time in the United States that allowed African Americans the opportunity to own beach front property. Inkwell Beach gained prominence as a safe haven and summer resort for African Americans, particularly after the Jim Crow era, despite its origins as a derogatory term. The name "Inkwell" was initially used by some whites in reference to the skin color of the beachgoers. However, the African American community later reclaimed the name, transforming it into a symbol of pride and a place of belonging

Another short and sweet walking circuit is located on Main Street in Vineyard Haven. Vineyard Haven is the other location in which the ferries dock. Similar to Circuit Ave there are lots of shops, restaurants and places to sit and look at the harbor that are all walkable if driving or taking the bus!

A Vineyard Haven favorite for authentic Italian food and cocktails! Usually very busy so a reservation is recommended!

At the "top" of East Chop drive, depending on where you start is the East Chop lighthouse. This boasts a beautiful view of the open ocean where your can watch the ferries and many boats pass by through out the day. East Chop drive is a widely know street and "loop" for people who want to walk, bike, run or drive to see some classic vineyard homes that have been in some families for generations and breath taking views. The front of the Greene family's home is located at the "bottom"/beginning of this very known hill!

Located in Annie's favorite part of the island, Larsen's fish market in Menemsha has the best steamers, fresh shucked oysters and clams you could ask for! Although "up-island" and around a 30ish minute ride from OB, it is the best place on the island to watch the sunset, but no matter when you go it's a special treat! The biggest port for the islands seafood, you will be sure to watch boats come in with fresh local seafood that will be eaten within that day!

Just next door from Menemsha is Aquinnah! Widely known for it's beautiful cliffs and clay that's been exposed by erosion from the sea over many years. Aquinnah which is formerly known as Gay head cliffs is a change of scene from most of the other parts on the island. Another "up-island" treasure, their are bus and bike tours available for anyone wanting to know more of the history located within the cliffs.

The Seafood Shanty is a great restaurant to enjoy seafood and beyond. Don't be shy to try their many options for frozen drinks and summer themed mixed drinks and beers. You have the option to eat inside but we recommend sitting outside and constant coming and going of boats in Edgartown Harbor and watch the little ferry that goes back and forth from Edgartown to Chappy aka Chappaquiddick.

A cute cafe behind a bookstore on Main street in Edgartown. Great food and drinks and while you're there take a look at the bookstore itself. It's very cute and cozy!

If you find yourself in Edgartown you will enjoy visiting and seeing the Chappy Ferry or known world wide as the ferry seen in the iconic movie JAWS directed by Steven Spielberg which was filmed on the vineyard! Chappy is a little island off of Edgartown which can only be reached by taking this little ferry. The ferry goes back and forth all day until midnight for cars and passengers to commute back and forth.

Fun fact: Chappy was home to the Greene family every summer for the month of August starting with Patty and Fred Greene for 40 summers in a row! They first came to Martha's Vineyard in their early twenties, fell in love with it, then introduced their families and friends and never looked back!

South Beach is a phenomenon on the vineyard because it allows you to be a beach go-er but you also get the option to have a unique experience of actually driving your own car on the sands and beaching' it whenever you like! (with a permit sticker and 4 wheel drive vehicle of course!

Fun fact:

Annie grew up beaching this way and had no idea that most people do not beach with their car! She had a harsh reality in middle school when going to the beach with a family friend and learned she had to walk and lug all of her stuff...(spoiled) Chappy is also famously known for their drive on beaches as well :)