Why Readers Shouldn’t Miss Hitting the Connecticut Book Trail on Independent Bookstore Day

Rambling readers, it’s time to saddle up and hit the trail — the Connecticut Book Trail.

Leave your chaps and lasso at home and round up your book-a-roos to celebrate Independent Bookstore Day on April 26 on the Connecticut Book Trail. This annual celebration on the last Saturday in April connects readers and bookstores to forge closer ties within the bookish community, revel in our First Amendment rights and support local economy. And what better way to do it than on the Connecticut Book Trail?

The Connecticut Book Trail

The Connecticut Book Trail is the brainchild of Meghan Hayden of Riverbend Books. She looked at the Passport Challenge started by RJ Julia in 2019 and wondered if it could become a year-round attraction, like the state’s wine trail. “I wanted to see if we could do something fun and sustainable that would invite bookstore tourism,” says Hayden, who was inspired by the Cape & Islands Bookstore Trail in Massachusetts and the Hudson Valley Book Trail in New York. 

And the Connecticut Book Trail was born.

There are 23 bookstores to visit on the 2025 book trail, including newcomers such as Diane’s Bookstore in Greenwich, the Telegraph Autonomous Zone in New London, Montgomery & Taggert in Chester and The Curious Cat in Winsted.  For the adventurous bibliophile who loves a challenge and is willing to circumnavigate the state from Old Greenwich to Mystic to Winsted and home, there’s the 2025 Passport Challenge.

Passport to Prizes

A special feature of hitting the Book Trail on Independent Bookstore Day is the invitation to join the Passport Challenge. Visit as many bookstores as you can April 26-27 to be entered in the drawing for more than $4,000 worth of prizes. Passports will be available online at CT Book Trail Passport Challenge that you can print out — or pick one up on the trail. 

For book lovers who want to travel at a slower pace, you have until Labor Day to visit all 23 stores to meet the Slow & Steady Challenge. You could be entered to win a gift card bundle that lets you spend $25 at each bookstore on the trail.

Sneak Peeks

There’s a bonanza of goodness awaiting trail-goers. Here’s a peek at just a few of the reasons not to miss Indie Bookstore Day on the CT Book Trail:

Wish RJ Julia a Happy Anniversary. The beloved grand dame of independent Connecticut bookstores is celebrating its 35th anniversary by giving back to the reading community. They’re teaming up with Reads to Grow to support early childhood literacy. The organization is bringing a school bus to fill up with books for young readers who need them. You can participate by buying or bringing books to fill the bus. (Talk about a magic school bus!) Donors will be treated to free ice cream. And don’t miss the bookish merch designed by art contest winners, special drinks in the RJ Café and scratch tickets for more fun surprises.

Win a year’s worth of audiobooks. Move over, Willy Wonka. Have we got a golden ticket for you! Find the golden ticket hiding in a participating store and be entered to win a year’s worth of free audiobooks from Libro.FM, which helps support indie bookstores. 

Romance the Book Trail. The state’s first romance bookstore, Montgomery & Taggert in Chester, will woo readers with their gorgeous special edition books, new handprinted tote bags designed by Chelbi Wade of Shell & Bee Studio, and a chance to “Giddyup & Get Inked” by their friend Amy Gabriela of Amygdala Ink Tattoo Studio who will offer a Western romance-themed flash tattoo popup. 

Get crafty and make kids happy. Parents can shop in peace while little readers enjoy crafts at Black Rock Books in Bridgeport. The Curious Cat in Winsted will send them on a wild cat chase as tiny booklovers search for a hidden toy cat to win prizes. 

Grab some victuals and libations. Riverbend Books will treat visitors to treats from local merchants, including handcrafted soda and freshly baked cookies. 

Go on a blind date with a book. Visitors don’t have to judge a book by its cover when they visit Bank Square Books in Mystic to select a free mystery book in a plain brown wrapper. Or enjoy a free advanced reader copy of a book yet to be published at participating stores.

Revel in the swag. Who doesn’t love charming stickers, mugs with relatable sayings, and whimsical tote bags? Participating stores will offer a wide range of merchandise, and a certain bookseller in Mystic plans to have Blackwing pencils for sale, not to mention exclusive merch just for the day.

Enter to win. There are still more ways to win on the Book Trail. Opportunities include prize wheels, raffles and giveaways, each as unique as the individual bookstore. 

Fall in love with a bookstore. There’s a store for every taste on the Connecticut Book Trail — and we won’t tell if more than one shop makes you swoon. From cozy book nooks, to hideaways of gently loved books, to shops where book jackets rub shoulders with vinyl album covers, to full-service emporiums, Connecticut Book Trail has it all. 

Spread the book love. If you can’t make it to Connecticut, your state might have its own book trail. In addition to the previously mentioned and inspiring trails on Cape Cod and upstate New York, there is the Montana Book Trail, the North of Boston Book Trail, Mass Book Trail and the Austin Book Trail. Don’t see a bookstore trail in your state or city? Talk to your favorite literary third space and make the suggestion. Independent Bookstore Day is a great time to spread the book love.