Stars Hollow IRL: Connecticut Towns That Feel Like a Gilmore Girls Episode

This article is written by a student writer from the Her Campus at U Conn chapter and does not reflect the views of Her Campus.

In honor of October’s arrival, the world has finally started to feel like fall. For some, fall may look like a pumpkin patch with friends or a spooky movie, and for others, it’s scenic drives and apple picking. And for a certain group (the best type of people, may I add), fall feels like Gilmore Girls. And because Luke’s Diner, The Dragonfly Inn and Miss Patty’s School of Ballet were all set on the backroads of Connecticut, here are 5 Connecticut towns to visit – Stars Hollow style!

LITCHFIELD

Located in the Northwest corner of Connecticut, Litchfield is a quintessential New England town. With beautiful conservation lands like White Memorial, a main street with boutiques and restaurants, and its very own Chilton Academy (The Forman School), Litchfield has many of the same attractions found in the show. 

One of the best parts about Gilmore Girls (in my humble opinion) is the fall foliage and beautiful houses seen around Stars Hollow. Luckily, you can find these, IRL, in Litchfield! Historic colonial homes, much like Rory’s, line Main Street, are often at their prettiest in the fall with leaves of every color on their lawns. 

What is there to do in Litchfield? Besides exploring boutiques and restaurants, you can enjoy the fall foliage on a hike at Topsmead State Forest, take a self-guided tour of the historic homes, or visit Thorncrest Farm, just a 5-minute drive away in the town of Goshen. 

For more ideas, check out this article written by a Connecticut explorer and enthusiast!

BURLINGTON

About 15 minutes east of Litchfield, Burlington is another small town. Adorning a one-room schoolhouse, Burlington offers various trails, farms and outdoor activities to enjoy in the fall! There’s even a fish hatchery (not as Gilmore Girls-esque), which I hesitantly obliged to visit with my dad last year. 

With a population of only about 9,000, Burlington offers many backroads to explore, and hiking options include the Tunxis Trails and the Burlington Falls, featuring waterfalls to enjoy. 

Although shopping and food options may be a bit limited in this town (sorry, no Luke’s Diner), there are many farms to get home-grown fresh snacks! Among these farms is Hogan’s Cider Mill, one of my all-time favorite places to go pumpkin picking.

KENT

If you’re craving the pancakes and eggs of Luke’s Diner, visit the town of Kent! Although known for its waterfall (Kent Falls) and its very own Chilton (The Kent School), Kent also has a wonderful main street filled with shops and restaurants. Looking for Luke’s Diner? Stop into The Villager for a quick bite to eat before taking a hike up Kent Falls or shopping at the Kent Barns.

Rory might not have liked hiking, but she did love her books. And luckily, Kent has books, and lots of them! Visit The House of Books, a bookstore for all ages and levels of reading (and if you’re even luckier, you might visit when they’ve moved their book collection outside to browse). 

Lorelai would’ve loved Kent for its weekly farmer’s market on Fridays all throughout October. Stop by for coffee, a sweet treat and many mother-daughter duos! And on October 26th, Kent will be hosting its annual Pumpkin Run (much like Rory and Lorelai’s Dance Marathon).

Check out this New York Times article for a feature on Kent (and Litchfield)!

WOODBURY

About 40 minutes from Kent is Woodbury, a town with historic buildings dating back to the 1600s! Beside a beautiful main street featuring these colonial homes, Woodbury is home to many antique shops (a must for Lorelai) and an alpaca farm (although I’m not sure if anyone from Gilmore Girls would put an alpaca farm on their itinerary – maybe Miss Patty). 

Another rural town, Woodbury offers many ways to enjoy the fall foliage: take a walk through Flanders Nature Center, Hogpen Hills Farms Sculpture Park or Walker Roads Vineyards. And if you’re a goat lover like me, make sure to check out Highwire Deer and Animal Farm. 

And the most dedicated Gilmore Girls fans will be happy to know that Woodbury is only a 15 minute drive from Washington Depot, the real Connecticut town that was the inspiration behind Stars Hollow! Read more about this inspiration here.

NEW HARTFORD

Last, but certainly not least, is New Hartford – a town for all seasons (but fall may be the best)! 

With a beautiful town library (where Rory would spend hours in, I’m sure), a main street with a consignment shop with treasures waiting to be found, a boutique with locally-crafted gifts, and a farm store for fresh-grown produce, as well as many hiking trails, New Hartford offers everything for a perfect Gilmore-Girls inspired day trip. 

Because you’ll need some energy to explore New Hartford, stop at The New Hartford Diner or Germain’s on Main for breakfast sandwiches or stacks of pancakes (or if you have a sweet tooth, you can find heavenly cinnamon rolls at Calo’s Cookies). 

Looking for some apples to pick or pumpkins to carve? Stop by Gresczyk Farms for pumpkins of all sizes and mums of all colors and Burdick Road Orchard apples, ciders and pies!

CONCLUSION

Remember all those clips from Gilmore Girls of the characters walking through Stars Hollow during the fall, dining at Luke’s and guzzling down coffee, or attending a fun small-town event on the green? With these Connecticut towns, these scenes can become a reality (just minus the camera crew)!

And while you walk these Connecticut towns, listen to the Her Campus 2025 Fall Playlist!