5 Best Bookstores on Martha’s Vineyard You Can’t Miss

Quick List of Bookstores on Martha’s Vineyard

There are three traditional bookstores to discuss and two bonus opportunities to find books on the island.

Details About the Bookstores on Martha’s Vineyard

While the Massachusetts island of Martha’s Vineyard is best known for its beautiful beaches, historic lighthouses, and New England charm, bibliophiles like me also deeply understand that it’s an amazing place to peruse bespoke independent bookstores.

Like most local bookstores, they each showcase the local cultural history in unique ways. I’ve taken my annual summer vacation at Martha’s Vineyard with my husband’s family since 2015, and it is, without a doubt, our “happy place.” We even got engaged there in 2018 (Menemsha Beach at sunset, in case you’re wondering)!

As a bookworm, naturally, one of the things that makes me happiest is perusing the local bookstores, especially for books set on Martha’s Vineyard. It’s a very literary-loving location, including an array of authors and book-loving visitors, including former U.S. President Barack Obama (as reported by Cape Cod Times)!

Let’s explore these bookish nooks and crannies, so you can plan to write your own next “page” of life in this special place.

Edgartown Books

Edgartown Books is a real treat for a few different reasons. Right in the shopping district of upscale Edgartown is a bookstore that’s hard not to love.

First, this two-story shop has stairs with bookish paintings that give it so much charm.

They carry new books but also have an exceptional selection of fiction and non-fiction local books. We always find ourselves flipping through their pages. Many of them have also been signed since they have hosted many author events!

Lastly, this is one of the best bookstores on Martha’s Vineyard because it has a cafe! Behind the Bookstore is located — you guessed it — behind the bookstore and offers a coffee shop, cocktails (at the aptly named Hemingway Bar), and fresh food (breakfast, lunch, and dinner) under the trees and a canopied tent.

It’s very popular and often VERY busy, especially during the summer!

Portobello Road

Portobello Road is an “eclectic boutique.” It’s one of my favorite stores to browse anywhere. It’s the perfect place to spend a rainy or chilly day with a warm beverage. You’ll see why…

Nestled into a tiny shop near our favorite Martha’s Vineyard restaurant (The Seafood Shanty, on whose deck we have spent countless casual New England meals) is a store that is filled to the brim with a mix of everything from books to art, home decor, stationery, and thoughtful gifts.

It gets better. Everywhere you look, there is something to see. Look right; a few books are stacked with a cute mug. Look right; there’s a canvas portrait next to some cute greeting cards. And they play the most relaxing music!

You can go back several times and have a different experience on each occasion — kind of like an antique store.

The book selection is also varied. While there are popular fiction releases, there are even more books that I would consider fun and unique that I haven’t seen anywhere else. I always leave with a list of books and items I want to add to my collection.

Bunch of Grapes Bookstore

On the port town of Vineyard Haven’s Main Street, right in the heart of Vineyard Haven, you’ll find the beloved Bunch of Grapes Bookstore — a staple of 40+ years. It’s a fairly traditional bookstore blending new releases and books of local interest, as well as some cute bookish trinkets. I spotted some of my favorite book earrings there.

It’s had many special visitors, including former U.S. President Obama.

Of special interest is that, as of 2022, it has a new owner (a former employee) and a new cat! “Bookmark,” the tuxedo cat, has become popular with customers. We found her people-watching in the window before the store opened. We went back to visit her again later, and we weren’t the only patrons craving her attention. She’s friendly and seems to be “used to” being popular.

If a bookish cat doesn’t make a bookstore unmissable, I don’t know what does!

Free Little Libraries

A Free Little Library is a community-driven book-sharing initiative, usually as a small wooden box placed in a public space. These “libraries” operate on a “take a book, return a book” principle, encouraging people to pick up a book they’re interested in and, if possible, leave one for someone else to read.

What I love about them is that you never know what you will find.

At the time of posting, there are six registered on the island. Personally, I always peek into the one just outside Back Door Donuts when we stop in for the famous, most delectable apple fritters imaginable (thank me later).

Your Accommodations

Finally, there is a fairly good chance your accommodations will have books accessible to you. Every rental we have stayed has, as Martha’s Vineyard is a book lover’s haven.

This past summer, we stayed at The Dexter in Vineyard Haven, and this expansive rental property had at least ten locations stocked with books.

Another fun fact is that I was reading on the beach in 2018, just before we got engaged, and I placed the book on the bookshelf at our rental home after that. We stayed there four years later, and the book was still there!

Conclusion

Now that your digital literary voyage to the bookstores on Martha’s Vineyard is complete, you are well prepared to plan your real-life journey to these uniquely charming bookish locations that have become “must visits” for me each Summer.

For even more, check out my favorite books set on Martha’s Vineyard, including Summer Sisters by Judy Blume and Summer Darlings by Brooke Lea Foster, who has become both a digital and real-life friend (after I spotted her at the Flying Horses Carousel) over years of discussing our favorite Martha’s Vineyard bookstores.

Lastly, check out my summer 2024 bookish moments on Martha’s Vineyard on Instagram: