The Real Life Stars Hollow: Litchfield, CT

This is a detailed article specifically about Litchfield, Connecticut.

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Litchfield feels a lot like an old colonial town. It is adorable and charming, but in my opinion, the least like Stars Hollow (of the four towns-Washington Depot, Litchfield, Kent, New Milford).

While Litchfield does have some Stars Hollow-y aspects, the architecture and the vibe of it just lend it more to a Revolution era town. It’s definitely worthy of being explored for that aspect, but honestly, as a Gilmore Girls town, I would say you can skip this one.

I didn’t visit any of the local restaurants in Litchfield, but I did visit the Tapping-Reeve House & Law School. I was very excited to find a “Scarecrows in the Field” festival going on while I was there! That was definitely a Stars Hollow type festival.

The traffic in downtown Litchfield was crazy! It was a weekend, so it would probably be less busy on a weekday.

The 4 Connecticut “Stars Hollow” Towns:

How is Litchfield, CT like Stars Hollow:

Town Green

Litchfield does have a town green, and it is enormous. It runs the entire length of shops along West St.

Mostly, it is just a bunch of grass (and no gazebo), but they do have a war memorial on the far end of the green. They also have an information booth in the middle of the green.

White Steeple Church

Litchfield has its fair share of historic buildings, including a beautiful white steeple church across from the town green.

Cute Downtown

The downtown district of Litchfield is adorable. There are a lot of shops and restaurants (and cute little shop signs) to explore.

Most of them seem to be on the fancier/pricier end though. I didn’t personally visit any of the businesses on West St., but it is a fun street to walk along!

Like I said above, it is a very charming town, but it definitely feels like a historic, colonial town rather than Stars Hollow (although I suppose Stars Hollow did play their part in the Revolution).

Antique Stores

You’ll find all sorts of antique stores all over the area. I only counted them specifically for a town if they were right in downtown.

I did find a couple in Litchfield. Jeffrey Tillou Antiques was a fancy looking antique shop right on West St.

South Street Antiques was just around the corner from the main street, in a charming house that could very well have been in Stars Hollow.

Tapping Reeve House & Law School


I visited the Tapping Reeve House & Law School in Litchfield, which is free to explore. Tapping Reeve started the first law school in the country, and he was married to Aaron Burr’s sister, so I was legitimately interested because… “Hamilton.”

But you seriously have to read his love letters to Sally Burr. They are the most adorable (and well written) love letters you will ever see!

It’s certainly a more authentic experience than the Stars Hollow history museum, but they did have a very Stars Hollow-y thing going on when I was there: a scarecrow festival!

I thought this one kind of looked like Lorelei!

Check out where they filmed episode 1 of Gilmore Girls in Canada:

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