Martha’s Vineyard is my happy place, so I know all the best things to recommend in this Martha’s Vineyard guide for travel with a literary twist.
It feels uniquely like that most American Summer vacation (from American flags, to sailboats, hydrangeas and the classic style that permeates the island), and it is comfortable with its cool New England air. We visit nearly every Summer, and we even got engaged there in 2018!
It’s a large island with very different towns that each have their own special features, so I am offering some of our best recommendations (with pictures!) from some of the most popular towns for your enjoyment of this magical spot.
Hotel Tips: Of note, we stay in a rental home each year, so I cannot personally recommend a hotel, but I have seen and heard great things about the Winnetu (and I have heard Steve Carell has stayed there). However, if you want a hotel that is walkable into town, you should look in the heart of Oak Bluffs or Edgartown. We have had drinks at the Harbor View Hotel, and it was absolutely gorgeous and luxurious, with a great view and walkable location in Edgartown.
Also of note, to me, Martha’s Vineyard is more about life experiences than next-level food experiences. While the food we have had there has always been good, we really haven’t had any major standout foodie type meals. For that reason, I am not going to personally recommend too many restaurants. You really can’t go wrong, but there aren’t many “musts” in terms of food alone.
Since this is a blog focused on book pairings, first, I recommend that you check out my list of the best books set in Martha’s Vineyard and my list of the best Elin Hilderbrand books (many of which are set in Martha’s Vineyard). I’ll sprinkle in some literary references below as well.
Without further ado, below is my Martha’s Vineyard guide for travel with a literary twist, categorized by the most popular locations we most often visit.
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Martha’s Vineyard Guide by Location
Oak Bluffs is the town where we usually stay in Martha’s Vineyard. It has a large harbor where ferries transport visitors and tourists, alongside a pier with local restaurants. We like to stop by the popular Nancy’s Restaurant (where Malia Obama worked one Summer) for a bite of American food with a New England twist and/or sushi and a cocktail with a waterfront view.
Oak Bluffs is the most family-friendly location in Martha’s Vineyard, with a main street, Circuit Avenue, filled with beachy boutiques, ice cream shops (I recommend Ben and Bills, as they have unique homemade flavors, including dairy-free options), arcades and coffee shops (I strongly recommend Mocha Motts for the best coffee and chewiest bagels on the island, but get there early to avoid a long line).
It’s also a fun tradition to get a deliciously fresh donut at the popular Back Door Donuts. The line can get long, and they sell out fast every day, but you can stop back at night to get a warm donut from the “back door” — an island tradition (a line forms for this as well).
Facing the ocean in Oak Bluffs is Ocean Park — an expansive and breathtaking park with lush flowers and a gazebo, surrounded by the most gorgeous Victorian homes.
Oak Bluffs is a fun town to explore. It’s known for a campground meeting place and its “Gingerbread Houses,” which look how you may imagine them to look, and are all colorful and unique. We like to take a leisurely walk around this area with a cup of coffee.
Oak Bluffs is also known for the “Flying Horses” — the oldest operating platform carousel in America (which was referenced in the book Summer Darlings, and I interviewed author Brooke Lea Foster about it).
You can also visit the East Chop lighthouse by bicycle or car.
In Oak Bluffs, however, you can generally walk to everything you may need during your stay, from the grocery store to the beach.
Edgartown is a very preppy and very New England, colonial style, old whaling town filled with white buildings and homes, American flags and plump hydrangeas. It’s simply beautiful.
As you head into Edgartown, you can stop at the “Jaws Bridge,” which is famous for being featured in the Jaws movie, and jump from the bridge into the ocean along with dozens of other tourists.
Once you get into town, you should visit our absolute favorite place in Edgartown — The Seafood Shanty, a waterfront restaurant with a second-floor deck (referenced in the book From the Corner of the Oval) and home to my husband’s favorite lobster roll on Martha’s Vineyard. It’s so relaxing to have lunch and watch the sailboats sailing through. It’s a great location to take a sailboat ride as well!
We love to privately charter the Tigress catboat for an afternoon sail with Captain Kurt. The catboat is known for its American flag sail, and Captain Kurt is known for his banjo-playing skills.
Edgartown is also home to high-end boutiques, like Lilly Pulitzer, The Black Dog and Vineyard Vines. It’s also where you take the short ferry to the peninsula of Chappaquiddick. And, lastly, it’s also home to the Edgartown lighthouse.
Vineyard Haven is a very residential town with a wharf by which ferries enter Martha’s Vineyard. (It’s a major setting in Elin Hilderbrand’s The Identicals). It has a small main street with some fun shops, including Bunch of Grapes independent bookstore.
It’s probably best known for The Black Dog Tavern on the harbor, for a fun dining experience and some quintessential Martha’s Vineyard “black dog” merchandise.
It’s a great town to visit when the weather isn’t the best for the beach or another outdoor activity.
Chappaquiddick is a very remote peninsula that you get to from a very short ferry off of Edgartown (on which you can take your car, but plan accordingly as the line can get very long). The main character in the book A Vineyard Summer lives there, and it’s a major plotline in Summer of ’69.
It’s unfortunately best known for the incident that occurred in the Summer of ’69, in which Senator Ted Kennedy drove off of a bridge there, and a young woman died.
We like to rent “beach Jeeps” with beach tags and take them onto Chappaquiddick (a/k/a “Chappy”). You can explore beautifully preserved nature and drive along the private beaches for a totally secluded day of relaxation.
Aquinnah has, to date, my favorite view on earth (and I honeymooned in Italy). It’s home to the Gay Head Cliffs. After a short walk to the top, you can view the most expansive and breathtaking view of the Atlantic Ocean as far as your eyes can see. You can also climb the Gay Head lighthouse for an even higher view. Pictures simply do not do it justice.
There are a few small shops and The Aquinnah Shop Restaurant with an ocean-facing deck that makes another great place to stop for a bite with a view.
And if you travel to the base of the cliffs, you can spend the day on the beach (be forewarned: it’s known for nudity).
Menemsha! It’s a small fishing village on the Southwest coast, featured in Jaws, with a small beach and a few small lobster shacks. It’s best known for the most glorious sunsets you can imagine, and every night, people bring their coolers and chairs and set them up to watch the sunset with a glass of wine and some lobster from the local shacks. It’s kind of like a drive-in movie where the movie is the sun, and everyone claps when it sets!
And I got engaged on a walk along a rocky jetty there, just before sunset, on July 19, 2018. We celebrated with a bottle of champagne with my husband’s family on the beach as the sunset thereafter!
My best advice is simply to get there early. The beach crowd leaves in the early evening around 5:00 p.m., and the sunset crowd quickly fills in thereafter. The parking lot is small and gets filled very fast. However, you can also take a shuttle there.
That concludes my Martha’s Vineyard guide for travel with a literary twist.
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