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I came to Philadelphia for a conference. I left with a renewed faith in what happens when people build something for — and with — their community. In Philadelphia, I found a treehouse full of free books and stepped into an indigo-walled sanctuary that celebrates women authors, artists and activists. Some cities reveal themselves through their food or architecture. Philadelphia revealed itself through its bookshops — radical, rooted, and relentlessly creative. In the spring of 2025, I spent three days in Philadelphia for a conference — and naturally, I couldn’t resist turning it into an #40BookshopsUnder40 adventure. After a lunch session on storytelling, I set off on my grand tour de bookshops, loosely mapped out but mostly guided by instinct (and local intel). Over sandwiches, a Philadelphian leaned in when I mentioned my side quest and insisted I visit Harriett’s Bookshop — “an avant-garde bookshop celebrating women authors, artists, and activists under the guiding light of Harriett Tubman.” She told me about their Deeply Rooted Trolley Tours: a three-hour hop-on, hop-off celebration of local food, culture, music, and history — all through the lens of community. Two minutes later, I had my destination. I called an Uber to Fishtown. Harriett’sFrom the moment I stepped inside Harriett’s, the air buzzed with energy. Deep indigo walls framed clusters of customers chatting, browsing, snapping photos. A woman asked for a picture with the owner, Jeannine Cook, who smiled, posed, then slipped back behind the counter. Jeannine opened Harriett’s just six weeks before the COVID-19 pandemic. Once I’d picked myself off the floor, I decided to trust my instinct and move forward with the bookshop anyway. She moved the store outside, selling books on a grab-and-go honor system. To her, reading is a basic need — and when she introduced a pay-it-forward system, customers began buying books for essential workers. Every corner of Harriett’s reflects her neighborhood: local honey, canned goods, herbal infusions, and a steady rotation of events created with the community. When I started, I had no idea how to run a bookshop. But I knew that the job that best suits my personality is one that is creative and that challenges me in a good way. Harriett’s allows me to hold space for my community and create the change I crave. Now, I feel that all I do is the most basic thing I know to do: serving my community. None of the events or initiatives you see here is of my own doing. They are all collaborations with members of the community. We each bring our offerings, and from that, other ideas and projects emerge. That’s how the Deeply Rooted Trolley Tours were born: In 2021, we were getting threats and I made a pact with myself to serve other local businesses and to protect them by highlighting them on the tour and bringing in customers. Each year, the tours center on a new muse. In 2025, it’s poet Sonia Sanchez and her piece Present — a reminder to stay rooted in our collective power. Harriett’s, named after Harriett Tubman, continues to champion women authors, artists, and activists — both inside the shop and across the city. Since my visit, Jeannine has even published her first book, It’s Me They Follow (HarperCollins). I left Harriett’s inspired and buzzing, ready to see what other corners of the city had to offer. Wooden Shoe BooksBack in Old City, my first stop was Wooden Shoe Books, a volunteer-run, nonprofit anarchist bookstore. A “Don’t be an asshole” sign greeted me on the sidewalk — a fitting welcome. Inside, the staff debated art forms and future collaborations. I liked the vibe immediately. Their shelves were filled with political theory, poetry, records, and zines — none of which I was in the headspace for that day. That’s on me. If radical literature and community organizing are your jam, Wooden Shoe Books will feel like home. There’s even a community computer in the corner and a “woke kids” section. It’s a place built for discourse and discovery. Brickbat Books
Head House BooksStepping into Head House Books felt like coming home. The front tables overflowed with new releases, their covers practically calling to be picked up. I spotted Evan Friss’ The Bookshop (always a good omen) and started narrowing down my choices. Then, a gentleman entered and announced, “There’s a new book about the Beatles. Do you have it?” The bookseller sighed. The customer couldn’t remember the title, only that he’d seen a New York Times review earlier that week. Curious, I googled it and handed him my phone. “That’s it!” he said, delighted. While the bookseller ordered it, he asked if she could recommend something exciting for his four-year-old granddaughter. I had a sense that he wasn’t so much looking for an “exciting” read per se, but wanted to find a book for his granddaughter that she might enjoy. “Nothing comes to mind, but you can check out the kids’ section in the back,” she replied, visibly annoyed. As a mother, I couldn’t help but step in. I told him about Rosie Revere, Engineer — a surefire hit — and wished him luck. Here was a customer eager to connect over books, but the bookseller seemed not to care enough to meet him there. It was a missed moment of joy. I quietly set down my stack and left empty-handed. Tree House BooksMy final stop took me north to Tree House Books — and it turned out to be the perfect finale. Named after the wooden treehouse inside (yes, you can climb it), Tree House is far more than a bookshop. It’s a nonprofit giving library. I met Emma Goldstein, who’s been with Tree House since 2017. Tree House Books was started in 2005 by people in the neighborhood who were trying to figure out what to do with an abandoned building. They began as a used bookstore but then quickly transferred to a completely free Giving Library model. We are a true community space where all are welcome. The shop runs entirely on donations, which means the selection is ever-changing — part treasure hunt, part miracle. We have all genres for all ages and always have an awe-inspiring selection. We have a full section featuring Black authors for children and adults, and that tends to be our most popular area! The adult shelves rival any Indie bookstore: fiction, nonfiction, poetry, art, spirituality. But the kids’ section is where the magic happens — overflowing with board books, graphic novels, and stories that spark curiosity. My favorite is getting to see what comes in through new donations and in turn helping our visitors to find great books! I also love getting to know the wide array of people who come in and the many people I've gotten close to in doing so through the years. In my twenty minutes there, I talked with at least five people: Deirdre was painting out front, Emma gave me a lay of the land, one of Tree House’s longest serving volunteers was onboarding a new volunteer, and I complimented Ja’Sonia on her outfit that day. And, of course, I chatted with other customers while browsing. I felt like I had walked into the home of one big, book-loving family. One day when I was signing in a new member I saw there was already someone in our system with the same name. We figured out that it was his father who had since passed away. It was very touching because he knew his father loved books but didn't know he used to come here. It made him so happy to reminisce on his dad's love of books that he had passed down to him. Emma's book recommendations
Philadelphia in a NutshellEven though I only bought one book on this tour, Philadelphia’s Indie bookshop scene blew me away with its range and spirit. From anarchist collectives to literary sanctuaries, every shop has its own rhythm and reason for being.
What stood out most were Harriett’s and Tree House Books — both punching far above their weight as community anchors. They don’t just sell books; they nurture literacy, belonging, and joy. If that’s not the heart of a great bookshop, I don’t know what is. Comments are closed.
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