WRITTEN BY SARAH COTTRELL
You’ve heard of a pub crawl, but have you ever tried a bookstore crawl?
If you live in or plan to visit Portland this summer, a bookstore crawl should be on your list of things to do, especially when you consider that the city has more indie booksellers per capita than almost anywhere in the country.
Bookstores are a magical place to spend your time and money. Not only can you find marvelous reads to enhance your life, but you can also find community and connection. If you’re not sure where to start, we recommend these iconic local indie shops:
Longfellow Books: 1 Monument Way, Portland
The anchor of Portland’s literary scene, Longfellow has been an independent community bookstore in Monument Square since 2000. Beloved for its staff picks, as well as its robust Maine section, you’ll quickly realize the book curation is top-tier. They keep a handy online calendar of upcoming events, including book launches and author talks.
Print: A Bookstore: 273 Congress St., Portland
Print is a bookstore for readers who like to keep up with the latest publications on prescient topics, with rotating staff displays on subjects covering a wide range. They take reading seriously, and to prove it, they have an action-packed events calendar, a rad newsletter, and a book club.
Back Cove Books: 651 Forest Ave., Portland
Located in the Odd Fellows’ Block in Woodfords Corner, Back Cove Books is community-focused to its bones; this is a lovely place where everyone belongs. Not only do they have books in every genre and for all ages, but they also keep a busy community events calendar with programming, author events, and book clubs.
Green Hand Bookshop: 661 Congress St., Portland
It is hard to miss this bookshop, with its iconic green hand painted on the massive windows. A labyrinth of secondhand, vintage, and antique books on every subject, it is located in Congress Square across from the Portland Museum of Art. While there may not be a robust events calendar, that’s OK because when you walk in, you will lose track of time in the incredible stacks of vintage books.
Carlson & Turner Antiquarian Books & Bookbindery: 241 Congress St., Portland
If you are a serious bibliophile, this is the bookstore for you. Housed in a Victorian-era building, the shop holds more than 40,000 antiquarian, scholarly, and used books, plus rare manuscripts, maps, fine art prints, and fun oddities. They are also a full-service hand bookbindery. Directly across the street is the oldest cemetery in Portland, dating to the 17th century — and they have the key.
Grump & Sunshine Bookshop: 40 Free St., Portland
A newer addition to the Portland scene with a cult following, Grump & Sunshine leans into its quirky identity with a curated selection that rewards romance readers. If you’re the kind of reader who loves browsing books and cool book merch, then this place is absolute heaven. To check out events, follow them on social media for pop-up announcements, including author signings, book clubs, and even holiday parties.
Sherman’s Maine Coast Bookshops: 49 Exchange St., Portland
This iconic local bookstore has roots dating to 1886 in Bar Harbor, and its locations now dot communities along the rugged Maine coastline, including Portland. You can find almost any genre of book here and enjoy an events calendar packed with author signings and more.
Yes Books: 589 Congress St., Portland
If you’re looking for an old-school secondhand bookstore with all the analog vibes of a record store, Yes Books is for you. While they don’t have a website, they do have the charm of floor-to-ceiling stacks, densely packed shelves, and a shopkeeper who knows where everything is. This is an experience you don’t want to miss.
Letterpress Books: 91 Auburn St., Portland
Letterpress Books is one of those super-friendly, small-town shops where the staff loves reading and wants to tell you about an amazing book you will love, too. If you want to see Maine authors highlighted, this is a place to start. Follow them on social media to find out about their regular author events, including meet-and-greets, book signings, and more.
Total Loss Books: 93 Washington Ave., Portland
Total Loss Books is the newest indie bookshop on the list, opening its doors in January 2026. While they do not appear to have a website, they do have a very cool Instagram (@totallossbooks) worth checking out for its curated, art-forward vibe featuring high-quality secondhand and rare books.
While a pub crawl usually lasts only one night, your book crawl may indeed take a whole weekend — or summer!