Gilmore Girls Day in Connecticut

Over two decades ago, the TV show Gilmore Girls was introduced to the world. Following the life of a single mom, Lorelai and her teenager daughter, Rory living in the fictional town of Stars Hollow, Connecticut.

I never watched Gilmore Girls until they made the revival for Netflix in 2016. I had just moved to Connecticut a few years prior and the excitement for the revival intrigued me to watch. I binge watched and was instantly hooked! I watch Gilmore Girls on repeat all the time, especially every fall!

Not only do I binge watch the show during fall, but I also roadtripped to the real towns that inspired Stars Hollow! The writer of the show spent two weeks in Litchfield County when she got the inspiration for Stars Hollow. There’s not a definite ONE town, but a few that makes up Stars Hollow. I went on this Gilmore Girls trip twice, both times were mid-October. I recommend this time of year because you also get the enjoy the beautiful foliage in Northwestern Connecticut.

Here’s a guide of how to have a Gilmore Girls day/weekend:

WASHINGTON DEPOT, CT

Mayflower Inn & Spa [Independence Inn]— The town of Washington gets the most recognition behind the inspiration of Stars Hollow because the writer stayed here. The grounds are stunning! I walked around the outdoor gardens. The screened porch off their restaurant is very dreamy! Don’t forget to look for the library nook.
Hickory Stick bookshop [Stars Hollow Books]— A small cozy bookstore that gave the vibes of bookstore that Rory frequented. They even had a small section for Gilmore Girls fans!
Washington Supply Co. [Luke’s Diner]— If you recall, Luke’s Diner originally was a hardware store when his dad owned it prior to his passing.
Washington Food Market [Doose’s Market]— The small town grocery store looks very similar to Doose’s Market.
Titus Park and Garage [Gipsy’s garage] — I stumbled upon this garage when I popped in a store nearby. It reminded me of Gipsy’s garage!

I found Washington, CT to have the small town charm that Stars Hollow portrayed on the show. The people were very friendly. On the day I visited there happened to be a farmer’s market! Don’t forget to stop in the Five Janes store for some Gilmore Girls merch.

*Washington Farmers Market. Held on Saturdays 10am-1pm from June to November.*

NEW MILFORD, CT

Gazebo — The gazebo on the town green in New Milford is very picturesque. I loved how it was dressed up with fall decor!
Canterbury School [Chilton] — The prep school resemblances Chilton, the school that Rory attended. The street takes you directly into the middle of the campus, you can see the gorgeous buildings from the car.
Theo’s Downtown Diner [Luke’s Diner]— There’s a long counter with stools to sit on just like Luke’s Diner. It had the small town vibes, there were many locals enjoying their breakfast or lunch with COFFEE!
First Congregational Church — Stars Hollow had a white church with tall steeple. While all towns I visited had at least one church, I thought this one was the most similar!

*One of the buildings at Canterbury School.*

I loved New Milford, but it is bigger than what Stars Hollow would be. I got a taste of the locals life in New Milford when I saw another farmer’s market and kids collecting donations for their football team. The layout of this downtown reminded me the most of Stars Hollow. There were plenty of restaurants, shops and businesses to visit.

KENT, CT

*Book sale at Kent Memorial Library. The sale runs every weekend from Memorial Day until October.*

I loved visiting this small town. There was a small town green where a political rally was taking place the day I visited - maybe they’re working on Jackson’s run for Mayor of Kent?! It was also a surprise to find a huge book sale at the library. My inner Rory could’ve spent hours looking through the books! I got a few books, of course. I popped into the local bookstore down the street from the library called House of Books. It is a beautiful curated bookstore. Kent had a small main street, but there were a few shops and restaurants. There was a church on the corner too.

WOODBURY, CT

*One of many antiques shops in Woodbury.*

Mentioned several times on Gilmore Girls, I had to stop in this town. It’s not far from Washington. Woodbury has an antiques trail where there are 10+ antiques shops. Most of them are located on Route 6, but you won’t come across anyone like Mrs. Kim!

LITCHFIELD, CT

This town is often mentioned as part of Gilmore Girls trip around Connecticut. I didn’t really see anything that jumped out at me with Stars Hollow vibes. It is a beautiful town to visit, so I wouldn’t discourage you to skip it. Check out the Tapping Reeve House & Law School!

NEW HAVEN, CT

The home of the bulldogs - go Yale! It’s highly recommended that you stop in New Haven, although you could easily take an entire day to explore it. So if you have more than a day to roadtrip around Northwestern CT and if you’re up for another hour drive down to New Haven, go check it out. The campus is stunning and beautiful, I always love to photograph the details, especially during fall!

I throughly enjoyed doing this Gilmore Girls roadtrip around Connecticut. While in Washington and New Milford, I ran across many others who were doing the same thing! The back roads that takes you from town to town are gorgeous and a great place to see the foliage. I loved how almost every town had the small town aesthetic with a church, gazebo, town green, libraries and a main street with shops/restaurants. It’s very quintessential New England!

"It’s just my favorite time of year. The whole world changes color.” - Lorelai Gilmore