The “Gilmore lore” runs deep in Connecticut.
Towns across the state have embraced their ties to the 2000s series “Gilmore Girls” in a lot of ways. Many fans who live here could name a town they thought was the most like the fictional town of Stars Hollow on the show, but the team behind Connecticut Public’s podcast “Generation Gilmore Girls” visited these five key places during their reporting process. And we’ve thrown in some places we wish the show featured, too!
Consider this your guide to exploring Connecticut, Gilmore-style.
Washington: The small town that inspired Stars Hollow
There is no town in the state called Stars Hollow, but the small western Connecticut town where creator Amy Sherman-Palladino actually stayed while writing the show pilot feels true to Rory Gilmore’s hometown. The town hall is surrounded by charming local businesses, like Five Jane’s clothing store and The Hickory Stick Bookshop.
Lisa Stein’s family has owned the Washington Food Market for decades — and it looks just like Doose’s Market on the show. Stein says a popular order is coffee, of course, but also their deli special No. 15.
“Fifteen seems to be most popular with people that actually work in town,” Stein said. “Turkey, bacon, pepper jack, chipotle mayo.”
As Stein points out a photo of her grandfather with former New York City mayor Ed Koch, she explains the town has long been a vacation destination for city folk looking to get away.
“Summer’s really busy. We call it the beach town with no beach,” Stein says. “We do have a lake!”
Thankfully, the “Gilmore Girls” vibe is best explored during the fall when the leaves change.
If you want to go exploring, remember to save your map app directions before you hit the road. Visitors should be prepared for limited cellphone service in the area, but the town offers free Wi-Fi with QR code access at the parking area near the market.
Here’s our map of places that may make you feel like you’re on “Gilmore Girls:”
A short drive from the market is The Mayflower Inn & Spa, where Sherman-Palladino and her husband overnighted. It’s also the reason why Lorelai Gilmore works at an inn. But book ahead – management reserves access to the property to paying guests and folks with dinner reservations.
Down the street from The Mayflower is The Po Cafe. It’s a breakfast spot that is not a former hardware store, but it does resemble Luke’s Diner in the way that close-knit community members might help themselves to a cup of coffee from behind the counter. Sherman-Palladino saw this happen somewhere in the area during her stay, and took notes. Lorelai does the same thing on the show all the time!
The nearby Frederick Gunn School in town may have also offered a little prep-school inspiration for Rory Gilmore’s fictional Alma Mater, Chilton. You can throw on a plaid skirt and catch a photo op near some ivy-covered brick walls on campus, or check out other points of interest at Explore Washington.
Washington was also home to the first-ever fan festival weekend for the show. We hear from the organizer of The Fan Fest Society in episodes 2 and 3 of the podcast, who says Washington is absolutely worth a visit. (The fan weekend has since moved to another coastal Connecticut town, Guilford.)
New Milford: The (slightly larger) small town that looks like Stars Hollow
Also in the leafy hills of Litchfield County, a short drive from the town that inspired the show, is another town that really looks like the set of Stars Hollow. In fact, we met Lockey Coughlin, a founder of the website starshollow.org, who claims New Milford is the real Stars Hollow. She and her daughter also co-own the local bookstore, Honeybee Books & Tea, which has a huge selection of the hundreds of titles Rory is spotted reading on the show.
At the center of New Milford’s town green sits a bandstand, which looks a lot like the gazebo in Stars Hollow, where Lorelai and Rory have a lot of their heart-to-hearts. Just don’t call it the gazebo — locals will correct you!
New Milford also has a cozy diner — not Luke’s — but Theo’s. The town has a converted hardware store, too, but it’s not home to a restaurant. It’s the Village Center for the Arts, where visitors can get crafting. There are also a few antiquing stops that could rival the shop run by Mrs. Kim on the show, including The Hunt near the town green and the further flung Elephant’s Trunk Flea Market.
New Milford is also home to the newer “Weekend in the Life” fan festival, organized by Decade Days LLC, which is featured throughout the “Generation Gilmore Girls” podcast in conversations with fans and cast members who attended the 2025 event.
Hartford: Home to the Gilmore grandparents — and so much more!
Connecticut’s capital city is home to Emily and Richard Gilmore on the show. It’s also the city that drew "Gilmore Girls” creator Amy Sherman-Palladino to Connecticut, because she wanted to visit the historic Mark Twain House.
An aspect of Hartford you actually can spot on the show is Pratt Street Historic District, a charming pedestrian-only street that appears to be featured in an exterior shot in Season 1. This feels like a big deal to fans we spoke to, since no members of the cast ever filmed in the state.
To celebrate that claim to fame, Pratt Street hosts Stars Hollow Saturday each fall, where fans flock to the street to see it all dressed up like the town on the show. You can hear fans from the event throughout the podcast mini-series, and meet the organizer in Episode 3 [LINK TO PODCAST SHOW PAGE EPISODE]! (If you’re in the area during the summer, rather than the fall, you can catch a dance lesson at the Salsa Socials, too!)
In addition to driving past the grand estates on Prospect Avenue, which looks like where Emily and Richard could live and home to the actual governor’s mansion, visitors could check out the Elizabeth Park Rose Garden. There’s also art at the Wadsworth Atheneum Museum of Art, family fun at the Bushnell Park Carousel, and delicious and diverse cuisine at Parkville Market.
Guilford: The coastal town home to the annual Firelight Event for fans
While the show is mostly set in what looks like the leafy hills of Litchfield County in northwestern Connecticut, the original fan festival organizers have started to host their annual autumnal “Firelight Event” on the coast of Long Island Sound. Hear footage from the fall 2025 event in the second and third episodes of the podcast!
Close to airports in New Haven and Hartford, the Guilford experience also offers visitors a classic New England town green, as well as a taste of fire-cooked Connecticut lobster, hot buttered lobster rolls, peaceful waterfront hikes and lots of history.
New Haven: The college town embraced by Rory and Richard Gilmore
We are shocked Lorelai and Rory are never seen chowing down on some New Haven-style “apizza” on the show, so we’ve added some pizza shops to our map. In addition to that, we had to highlight a delicious Chinese restaurant that looks a lot like the one where Logan Huntzberger takes Rory and Marty to dine.
Although New Haven seems to lack a Luke’s-style diner, there is an amazing classic 1950s chrome diner that serves Indian cuisine near the Yale School of Drama, called Tandoor.
If you’re in the mood for sit-down breakfast and coffee, The Pantry and Bella’s are two great options. Rory probably would have browsed titles at Atticus or Book Trader Cafe white waiting for a latte and breakfast pastry to-go.
Of course, you will probably want to walk Yale University’s campus a bit to get a taste of Rory and Richard’s college experience. We did just that in Episode 3 of the podcast! We learned that on the show, Yale has coffee carts, but on campus, students stop by The Jitter Bus coffee truck. Rory would also want you to check out the Gutenberg Bible at Yale’s rare books library, The Beinecke, and for good luck, rub the toe of the Woosley statue. Book a tour with the Yale Visitor’s Center if you want to learn more!
