Martha’s Vineyard is such a popular destination in the summer, but I’m here to tell you, that fall on the Vineyard is truly the best time to visit.
Once the last of the tourists depart on Monday of Labor Day Weekend, the islanders take a deep breath, and reclaim the Vineyard as their own. I know this, because I lived on the island for many years, and September and October were always my favorite months. The water is still warm (in September), the restaurants are still open (but you don’t have to wait an hour for a table), the shops are having all their sales, there is no traffic, and everyone is more relaxed and happy.
While I don’t live on the Vineyard anymore, I still love visiting in the fall. My family and I have made a tradition of going over for a day trip to Edgartown during Columbus Day weekend, and I’m here to share all of our favorite spots.
Main St. Edgartown’s Main St. is quintessential “Vineyard”. It has cute boutiques, variety of restaurants, and cobblestone sidewalks.
Once you get to the Corner Store, take a left, and stop over at Mad Martha’s for an ice cream treat (black raspberry is my all time favorite there). You can eat inside, but I like walking over to the Vineyard Square Hotel, sitting on a bench, and people watching.
North Water St. This is my most favorite street on the Vineyard. This is the heart of historic Edgartown, with “Captain Homes” lining both sides of the street. It’s just so picturesque.
Harbor View Hotel This is the hotel that I would recommend to anyone coming to the island. But it is also my favorite for grabbing a glass of wine, sitting down on a rocking chair on their wraparound porch, and enjoying the amazing view of Edgartown Lighthouse and the harbor. You don’t have to be a guest to enjoy a beverage by the way and both restaurants are open to the public.
Edgartown Light House You can walk down to the lighthouse from Harborview Hotel, it’s an easy 5 minute walk, but your shoes will get sandy. It’s a pretty walk, with a view of the harbor, sailboats, estate homes, and of course the light house. If it’s open, I recommend going up to the top for the view. If the weather is warm, you can also lounge on the beach behind the light house, with a direct view of Chappaquiddick Island.
Atlantic Fish & Chop House There are a ton of great choices for food in EDG, but I have always been a fan of Atlantic. The food doesn’t disappoint, and they have a great wine and cocktail menu. I would argue that their view is the best, but the deck of the Seafood Shanty wins there.
Daniel Fisher House Has a lovely garden, that is open to the public and Elle loves the fairy tale gazebo for hide and seek.
Take the 6:15 p.m. Steamship Authority ferry back if you’re not staying on the island, and maybe you’ll get a magical sunset to end your fabulous day.
xo, Anastasia
