Gilmore Girls Weekend in Connecticut - Litchfield County

1. The Mayflower Inn and Spa - Washington

A must-visit for any Gilmore Girls fan! Stay at the stunning hotel that inspired the series’ creator. Channel your inner Lorelai working at the Independence Inn with Michel, savor one of Snooki’s delicious meals, or treat yourself to a spa session—because sometimes you just need to feel like Emily Gilmore at her DAR Club outing. Plus, the hotel is gorgeous especially during fall season.

2. Marty's Cafe - Washington

Every true Gilmore Girl knows you need coffee first! Marty’s Cafe is the perfect place to kick off your day. Cozy and full of local charm (unlike Luke’s), it’s all about that homey, community vibe. Sip inside or grab your coffee to go and stroll the town.

3. The Po Cafe - Washington

Stop by for a cozy cup of coffee and a hearty meal where Snooki’s fun energy meets Luke’s classic diner. From staple eats to sweet treats, this spot has something for every craving. Sip your coffee slowly, savor a bite, and soak in the warm atmosphere. It’s the perfect mix of comfort, charm, and a little bit of small-town magic.

4. The Hickory Stick Bookshop - Washington

No Gilmore Girls outing is complete without a bookstore stop. Rory would spend hours at Hickory Stick Bookstore. You might even feel some Team Jess vibes! This quaint shop even has a section dedicated to all things Gilmore Girls, making it a must-visit for fans.

5. Frederick Gunn School - Washington

Any OG Gilmore Girls fan needs a Chilton-inspired stop, enter Frederick Gunn School. This private prep school has all the classic New England vibes. You can easily imagine students like Paris and Tristan strutting down the halls.

Be sure and make a stop in New Milford on a Gilmore Girls Weekend in Connecticut!

6. New Milford's Green - New Milford

Your iconic Stars Hollow gazebo photo is waiting! This charming spot has been the backdrop for so many memorable town events and unforgettable scenes—from Luke and Lorelai’s wedding to Rory’s big “I’m pregnant” moment. It’s the perfect place to snap a photo, soak in the small-town charm, and imagine yourself right in the heart of all the Gilmore Girls magic

7. Lee's Antiques - New Milford 

Though a smaller role, Mrs. Kim is unforgettable with her strict personality and her home with an antique shop on the first floor. Lee’s Antiques gives you a little taste of Kim's Antiques. Take your time wandering through the charming shop, browsing the unique treasures, and imagining the quirky charm of Mrs. Kim herself. Who knows what hidden gem you might discover along the way?

8. Honeybee Books and Tea Store - New Milford

Trust me- you won’t leave without grabbing their famous Stars Hollow tote! It’s the kind of keepsake that practically begs to come home with you. And since it’s a bookstore, every corner is filled with charm, cozy nooks, and the perfect spot to channel your inner Rory. Between browsing the shelves and soaking in the small-town vibes, it’s an experience made for true fans who love both stories and souvenirs.

Gilmore Girls Weekend in Connecticut  - New Haven County

Yale is a must-see Stop for a Gilmore Girls weekend in CT. 

9. Yale University - New Haven

A must-visit for any Gilmore Girls fan - Rory’s time at Yale and it’s  where Team Logan originated. Explore the campus on a guided tour or at your own pace while soaking in the iconic spots while feeling like Logan in the Life and Death Brigade. Don’t miss the Old Campus Courtyard for that classic Yale atmosphere. Then add a stop to Sterling Memorial Library to imagine Rory studying for her one of her classes. Durfee Hall inspired Rory and Paris’s dorm room and a perfect photo setting. Lastly, the Yale-Harvard game is legendary. While not featured in the show, catch the atmosphere at the Yale Bowl for a taste of the rivalry.

10. Yale Campus Store - New Haven

It may not have the full Gilmore Girls atmosphere, but swing by the campus shop to pick up a Yale sweatshirt. It is a fun way to show some love for Rory’s college. Whether you’re grabbing a keepsake or just want a cozy souvenir from your visit, it’s a small nod to your favorite Stars Hollow student and her Yale adventures.

11. Guilford's Town Green - Guilford 

While in New Haven, take a quick drive to Guilford. The downtown practically screams Stars Hollow, just without the gazebo sadly.  Wander through quirky little shops, peek at a stunning historic church, and eat at one of the many delicious restaurants. Soak up the slow-paced, small-town vibes where lingering is not just allowed, but it’s encouraged.

12. Strawberry Hollow Farm - Guilford 

A local favorite, Strawberry Hollow Farm feels like it belongs in Gilmore Girls. From the charming farm to the cozy gift shop, it’s a fall photo paradise. The farm goes all out for autumn. Truly, it’s only open from Labor Day through Halloween (yes, seriously!).

Gilmore Girls Weekend in Connecticut: Fan Festivals 

13. "A Weekend in the Life" - New Milford

“A Weekend in the Life” takes place on September 12–14, 2025, in New Milford, Connecticut. The festival features Q&As, celebrity panels, bingo, trivia, and access to crafts. Standard passes give you access to the main event as well as select parties throughout the weekend, letting you enjoy panels, games, and community activities. Upgraded passes take the experience even further, offering private meet-and-greets with celebrity guests, opportunities for photos and autographs, and entry to additional celebrations like the Friday Night Bash and the Saturday Harvest Festival. The ultimate fan experience you won't forget!

14. The Firelight Event  - Guilford

Held in Guilford, Connecticut, The Firelight Event takes over an entire weekend each October (October 17 - 19, 2025). Join fellow fans for activities inspired by the show—like a knit-a-thon or scavenger hunt. Additionally, exciting experiences such as cast meet-and-greets, live podcast panels, and more. It’s the perfect way to celebrate everything you love about Gilmore Girls.

Lead image: Bryan Memorial Town Hall, Washington CT