The Real Life Stars Hollow: New Milford, CT

This is a detailed article specifically about New Milford, Connecticut.

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New Milford was my favorite of the four towns (Kent, Washington Depot, New Milford, Litchfield). I personally thought it felt the most like Stars Hollow. At least, as long as I stayed in the downtown area.

The downtown is cute and thriving, and is located right around the New Milford town green. While most of the restaurants and shops don’t really correspond to a specific one in the show, there are plenty to choose from!

And talk about a downtown with a view! Most importantly of all, New Milford has a centerpiece: the gazebo!

For me this really ties the town together and gives it that feeling of small town charm. So even though it doesn’t have as many specific Stars Hollow elements as some of the other towns, I think the layout and design of the downtown area feels the most akin to it.

But I do have to mention, the fact that you can drive two minutes down the road and suddenly be surrounded by shopping plazas and chain stores does destroy a bit of that Stars Hollow illusion.

The 4 Connecticut “Stars Hollow” Towns:

How is New Milford, CT like Stars Hollow:

Gazebo & Town Green

The gazebo is without doubt the shining star of New Milford’s claim to Stars Hollow-ness. The seasonal decorations add even more charm.

I love that the gazebo is located in the town green, right in the midst of the action! So you can get yourself a pumpkin latte at one of the coffee shops downtown, pop a squat in the gazebo and sip your drink while you gaze out at the pretty churches and downtown buildings.

Maybe you’ll even be around for a farmer’s market or a concert on the lawn!

Cute Downtown

New Milford’s downtown is packed full of adorable shops to explore. The variety is astounding! From coffee shops and health food places, to toy shops and thrift stores, to banks and businesses, there’s a lot going on here.

It’s a fun town to explore, whether you like Gilmore Girls or not. There aren’t a lot of businesses that specifically remind me of any in Stars Hollow, so I guess they lose points for that. It’s really more of the feel that I get from being here though, that really feels like Stars Hollow to me.

I did find an old red barn (part of New Milford’s barn quilt trail—how Stars Hollow is that!) that could definitely be Miss Patty’s.

Part of the New Milford Barn Quilt Trail.

White Steeple Church

At the far end of the town green is the classic Connecticut white steeple church.

It’s one of the prettiest sites in New Milford. I love that you can sit in some of restaurants across the street and enjoy the view!

New Milford Historical Society & Museum

I didn’t visit the New Milford Historical Society, but a local history museum is part of the Stars Hollow experience. Of course, it’s also a little less fun when the exhibits aren’t so ridiculous that you need to get down on your knees with a flashlight and peer through the broken floorboards to see them.

The museum is part of the barn quilt trail though, so you’ll definitely have to make a stop here as you chase down that small town gem.

Bank Street Theater

The Bank Street Theater is nothing like the Black, White and Red theater in Stars Hollow. You’re not going to be sitting on old couches, eating the bad burgers and fries you brought in with you while watching Pippi Longstocking.

So as far as Stars Hollow feel, it’s not really.

But it is something fun to do while you’re out exploring small town America.

Theo’s Downtown Diner

Theo’s Downtown Diner in downtown New Milford, Connecticut. They are only open for breakfast and lunch, so plan accordingly.

Serving breakfast and lunch right in downtown New Milford, you couldn’t get much closer to a Luke’s-esque diner than Theo’s Downtown Diner!

I didn’t eat here myself, but I’m sure the experience would be quite similar to eating at Luke’s (though maybe without the grumpy man in plaid).

See where they filmed episode 1 of Gilmore Girls in Canada:

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