Bookstore CrawlS Are The New Girl’s Night Out
Bookstores, wine, and friends? Girl’s night out just got so literary. Here’s where to crawl next.
Welcome to the era of the bookish bar hop. In this roundup, we’re reframing bookstores as the new social playgrounds—perfect for flirty page-flipping, annotated margin confessions, and a curated cocktail list to match. Whether you’re in NYC, LA, or Chicago, we’ve plotted your next very aesthetic girl’s night: think bookstore → wine bar → indie dinner spot. Cozy chaos meets chaotic good.
This is not your college pub crawl. This is a bookstore crawl—a literary girl’s night with better lighting, better conversation, and honestly, better flirting. The vibes are “intellectual with a hint of red lip.” Bonus points if someone leaves with a number scribbled in the margin of Normal People.
Below, we’ve rounded up the best crawl-worthy cities—and the indie bookshops, wine bars, and intimate restaurants that pair as well as pinot and Proust.
What To Wear To Bookstore Crawls
Shop The Look
New York City
A little chaotic, very charming—just like your group chat.
Start: Rizzoli Bookstore – Elegant, cinematic, and basically what a hardcover version of your Pinterest board would look like.
Sip: Dante – A cocktail bar that makes negronis feel like personality traits.
Snack: Bar Pisellino – Italian small plates, perfect for debating book boyfriends over burrata.
Bonus Points: Walk to Three Lives & Company in the West Village to keep the literary energy high and the Instagram grid cohesive.
Los Angeles
The only crawl where you might spot a celebrity reading Murakami.
Start: Now Serving – A cookbook-focused bookstore in Chinatown that turns foodies into flirts.
Sip: Verve Wine – Sip something biodynamic while arguing whether the main character was the problem.
Snack: Bestia – Bold flavors and dim lighting = the perfect book club after-party.
Bonus Points: Grab a poetry zine from Stories Books & Café on Sunset before heading out.
Chicago
For the girls who romanticize lake winds and annotated paperbacks.
Start: Unabridged Bookstore – Queer-friendly, cozy AF, and organized in a way that makes your Virgo friend tear up.
Sip: Rootstock Wine Bar – A spot that says, “We read the classics, but we’re not boring.”
Snack: Daisies – Handmade pasta and house-infused amaro? Sold.
Bonus Points: End the night with a walk around Logan Square with a new book in hand and zero regrets.
Austin, TX
For the girls who wear cowboy boots with their cardigans.
Start: BookPeople – The largest indie bookstore in Texas with creaky floors and a poetry section worth a full-blown breakdown.
Sip: House Wine – Think cozy backyard vibes, live music, and flights for indecisive girlies.
Snack: Lenoir – Intimate, lush, and the kind of spot where you’ll want to quote Sally Rooney across a candlelit table.
Bonus Points: Check out the in-house events at BookPeople—author signings that double as meet-cutes.
San Francisco, CA
Fog, fiction, and flirting with someone who definitely writes code and short stories.
Start: City Lights Booksellers & Publishers – Iconic, historic, and filled with the kind of books that make you feel smarter just holding them.
Sip: Birba Wine Bar – A low-key hideout tucked in Hayes Valley with a curated wine list as aesthetic as your group’s outfit coordination.
Snack: Zuni Café – Cult-favorite roasted chicken, moody ambiance, and the unspoken rule that everyone reads here.
Bonus Points: Swing by Green Apple Books in the Inner Richmond for a double-bookstore moment.
Philadelphia, PA
For the soft-core academia girlies who highlight in four colors.
Start: Uncle Bobbie’s Coffee & Books – Black-owned, community-driven, and the kind of place that serves espresso with a side of enlightenment.
Sip: Bloomsday Café – Wine, charcuterie, and literary energy in historic Society Hill.
Snack: Suraya – Lebanese food in an interior that looks like the inside of a Kinfolk magazine spread.
Bonus Points: End the night at Giovanni’s Room—the oldest LGBTQ+ bookstore in the country and a certified heartstring tugger.
How to Plan Your Own Bookstore Crawl
Pick three stops: Bookstore → Wine Bar → Dinner Spot. Option to repeat if the group has stamina and/or espresso martinis.
Theme your night: Romance novels? NYT Notables? Hot Girl Essays? The vibe is up to you.
Dress code: Something that says “I annotate in gel pen” but can also survive a wine spill.
Icebreaker game: Each person brings a book rec and reads their favorite line. Most dramatic delivery wins a drink.