The Real-Life Connecticut Small Town That Inspired Gilmore Girls’ Stars Hollow

As my fellow Gilmore Girls fans know, the show is based in Connecticut, so while I was out exploring the state, I had to check out one of the cities that inspired Stars Hollow! I drove about 65 miles west of Hartford to New Milford, and I instantly felt transported to Stars Hollow as soon as I pulled into town!

New Milford Town Green
25 Main St, New Milford, CT 06776

New Milford’s gazebo is located right in the heart of the Town Green. While I was researching which Gilmore Girls inspired cities I wanted to check out, I was sold on New Milford as soon as I saw the gazebo!

First Congregational Church
36 Main St, New Milford, CT 06776

This church looked so much like the Stars Hollow House of Worship, and it even had a similar looking steeple.

Theo’s Downtown Diner
14 Railroad St, New Milford, CT 06776

This diner resembled Luke’s and even has nods to the show with some of the decor they have on display. I ended up eating brunch here and the food was delicious!

Canterbury School
101 Aspetuck Ave, New Milford, CT 06776

This private boarding school was so picturesque and reminded me of Chilton Prep! It was a bit further from the downtown area, but just a quick five minute drive down the street.

I’m also including some additional photos from around New Milford while we were there - no matter where I turned, I felt like I was living the Gilmore Girls small town life!

Are you a fan of Gilmore Girls? Let me know in the comments below!

xo,
Keshia