Join the Adventure at Side Quest Books & Games

Published January 2025

In August 2024, a corner of Bow Market got cozier thanks to Caroline Sheridan, owner of Side Quest Books & Games. Starting with pop-ups in breweries and local markets in 2023, Caroline carved out a community of fantasy lovers and book nerds who flocked to her events. Side Quest’s physical location offers a magical oasis for literature lovers, right in the same neighborhood Caroline is raising her family.

Tell us a little about your business!

We’re a woman-owned, fantasy-inspired shop for magical books, indie role-playing games, and nerdy knick-knacks — all centering on underrepresented creators. We believe that stories are magic, that the best ones come from where you least expect it, and that there's a story out there for everyone!

What inspired you to start a business? How did this feeling grow once you actually started your business?

Like any good English major and life-long fantasy reader, I've always wanted to own a niche genre bookstore. But when I started playing tabletop role-playing games (like Dungeons & Dragons) about ten years ago, that dream morphed into something new; a store that celebrated fantastical stories of all kinds, no matter whether they were being read, written, played or imagined. 

Coming out of the pandemic, I knew that I wasn't the only one craving in-person community again, so I figured I'd do a little experimental pop-up at a brewery just to see what the response would be like. When nerds of all stripes started coming out of the woodwork, I knew I had struck a nerve, and then when the opportunity came around to put down my adventuring pack at Bow Market, I couldn't say no! 

Having the physical space now has given us so many new ways to engage the vibrant nerdy reading and gaming community around Somerville, and I can't wait to see where 2025 will take us.

What aspect of your business makes you most proud to be a business leader in our community?

We're the only woman-owned game store in Boston, and our dedication to being a safe and inclusive space for women and marginalized folks in tabletop gaming has enabled a really special community to grow. 

We held our first "Campaign for a Cause" charity event in November, and raised $4,000 for both the Massachusetts Trans Emergency Fund and the Palestinian Children's Relief Fund, and I'm bowled over every day by the care, kindness and generosity of our community.

How do you #LoveUnionSquare?

Being able to connect with the residents of Union Square and the surrounding areas is so special.  When I walk around the area now, I feel like I see my regulars all over the place and get to wave hello or stop and chat. Union Square feels like home!

If you were to plan the perfect outing in Union Square, where would you go and what would you do?

Morning coffee and pastry from Bloc, play time at one of the wonderful parks (for the kiddos), lunch from a Bow Market vendor, retail browsing on Bow Market's balcony, afternoon coffee and sweet treat from Maprang, sunset reading on one of the benches on Prospect Hill, dinner at Field & Vine, then finishing up with drinks at backbar!  

Do you have any "behind the scenes" or fun facts that a customer might not know already?

We have a packed event calendar, from book clubs to large game nights to smaller, professionally-run private games! We drop the next month's events around the 15th of the current month, and the way to snag tickets before they sell out is to subscribe to our Eventbrite profile (it'll update you automatically when new events get created — even before they're posted to Instagram!).

Is there anything else you think a Square customer would like to know?

Fantasy, sci-fi and role-playing games are so much more diverse, nuanced, and multi-faceted than you might think. Our favorite thing is helping folks find the perfect story for them, so come hang out with us! We'd love to talk nerdy with you!

Side Quest Books & Games is open on the second floor of Bow Market. Stop by Wed, Thurs, and Sun 12-6pm and Fri & Sat 12-7pm. Follow Caroline & Side Quest’s adventures on Instagram and Discord.