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Explore the best bookstores on Martha’s Vineyard from the perspective of a “regular” Summer visitor and book blogger, including everything you can’t miss and what’s unique about each one.

bunch of grapes bookstore in vineyard haven ma

Quick List of Bookstores on Martha’s Vineyard

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

The three major towns on Martha’s Vineyard each have literary offerings for you to explore:

  1. Edgartown: Edgartown Books and Portobello Road
  2. Vineyard Haven: Bunch of Grapes Bookstore and Free Little Libraries
  3. Oak Bluffs: Free Little Libraries

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 also 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 on 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)!

And as a bookworm, naturally, one of the things that makes me happiest there 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

staircase at edgartown books in edgartown ma

Edgartown Books: 44 Main Street, Edgartown, MA 02539

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 on them that give it so much charm.

They carry new books but also have a really exceptional selection of local books, both fiction and non-fiction. We always find ourselves flipping their pages. Many of them are also signed since they host so many author events!

Last but not least, 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 coffee a 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

books at portobello road in edgartown ma

Portobello Road: 4 Dock St, Edgartown, MA 02539

Portobello Road describes itself as an “eclectic boutique,” and it is 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, and you may find a few different books stacked with a cute mug on top. Look right, and there’s a canvas portrait next to some cute greeting cards. And, they are usually playing 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 in nature, and while there are definitely popular fiction releases, there are even more books that I would consider to be both 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

bookmark the cat in the window at bunch of grapes bookstore

Bunch of Grapes Bookstore: 23 Main Street Vineyard Haven, MA 02568

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 over the years, including former U.S. President Obama. And, of special interest is the fact that, as of 2022, it has a new owner (a former employee) and a new cat!

“Bookmark” the tuxedo cat has already become popular with customers. We found her people-watching in the window before the store opened. We went back in 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

free little library in oak bluffs ma

Four registered locations at the time of posting:
-Post Office Square, Oak Bluffs, MA (near the famed Back Door Donuts)
-111 Dukes County Avenue, Oak Bluffs, MA
-350 Lake Street Landing, Vineyard Haven, MA (at a public boat dock)
-177 Edgartown Road, Vineyard Haven, MA (outside a private home)

A Free Little Library is a community-driven book-sharing initiative, usually taking the form of 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 are going to find.

At the time of posting, there are four 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

@theliterarylifestyle ❤️❤️ #itendswithus #itendswithusbook #itendswithusedit #itendswithuscolleenhoover #colleenhoover #colleenhooverbooks #coho #cohobooks #booktok #booktoker #booktiktok #booktiktoker ♬ Sunset Key – Luis Duran

Finally, there is a fairly good chance your accommodations will have books accessible to you. Every rental at which we have stayed has, as Martha’s Vineyard is definitely 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 in it that were 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 thereafter. We stayed there exactly four years later, and the book was still there!


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.

Share your favorite place to get books in Martha’s Vineyard in the comments below.

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