Visiting The Towns That Made Gilmore Girls | Stars Hollow, CT

Gilmore Girls is a TV-show that has the coziest small-town charm in it. It was a perfect fall day when we decided to visit the real Stars Hollow. Did you know there is more than one?

The fictional town is just a set, but there are still a handful of Connecticut towns, very close to each other, that served as inspiration for the writer, Amy-Sherman Palladino when she created everyone’s favorite small town, Stars Hollow.

As a preparation for our day trip to the real town of Stars Hollow, we have prepared ourselves to get in the mood. Not only have we watched the show, but we are also dressed accordingly. Dressing for the destination, is in our opinion, something that makes it more fun. In this case, my plaid shirt is on, a baseball cap backward, and my wife is wearing an outfit that both Rory and Lorelai would fight over. We are ready to experience a day as a Gilmore Girl …plus Luke. The road trip is a scenic loop, click to see it on a map.

New Milford, CT

The first destination for our Gilmore Girl day is, New Milford. The gazebo in the park looks to us as we just stepped onto the filming set. Decorated and ready for a fall festival, it really reminds us that an important ingredient for any small town’s charm is a gazebo.

New Milford feels the most like Stars Hollow to us with its revolutionary history and Victorian buildings lining the streets. The town green, library, church steeples, and small businesses all add to the illusion of walking through Stars Hollow when school has been let out and the town is bustling.

For the exact location of New Milford, CT – CLICK HERE

Washington Depot, CT

The next stop is Washington Depot, the town that is said to have inspired Amy-Sherman Palladino when she stayed at the Mayflower Inn. It is not difficult to see a clear resemblance to Stars Hollow’s Independence Inn.

There’s also a Food Market like Doose’s (Washington Food Market) where you can totally picture Dean packing groceries and across the way a beautiful bookstore called The Hickory Stick Book Shop.
Next door is “Marty’s Cafe” which might not look exactly like Luke’s Diner but on our day trip it represents it in spirit. It is a nice cozy spot in the center of the town. The coffee tastes great and the treats would make any Gilmore Girl proud.

Finally, the inspiration for Chilton School is most likely “The Gunnery“, a boarding college located in a green and beautiful corner of the town.

For the exact location of Washington Depot, CT – CLICK HERE

Litchfield, CT

The last stop for our day trip is a town where Luke briefly lived called Litchfield. It very well fits all of the criteria to be “a real Stars Hollow town”. As the sun sets, we find ourselves on a bench in a beautiful park watching this little town just live its charming pace. We realize that the real life Stars Hollow is not only one place to find, it is the best of many.

It’s the families and townsfolk that make the heart of any town feel like “Stars Hollow”. It is things like used book sales, antique stores in old barns, and small town festivals. It is moments like when the cafe owner knows how you like your coffee or when you bump into a friend on the town green knowing you’ll do the same again tomorrow?

For the exact location of Litchfield, CT – CLICK HERE

MORE GILMORE GIRLS INSPIRATION:

Gilmore Girls Fan Fest
A Gilmore Girls celebration in the charming town of Kent, CT (also a worthy Stars Hollow destination).

Finding Stars Hollow
An amazing and very helpful site for anything Stars Hollow.

Explore Essex, CT
Another small town that reminds us of “Stars Hollow”.

Drink Coffee like a Gilmore, made by Luke himself, Scott Patterson.
If you order it, don’t forget to tell him that “It’s a Charming Life” sent you.

We hope you enjoyed our day in the real life Stars Hollow. Let us know if you live near a town that is “Stars Hollow” for you.

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Bye for now,
Lindsay Dianne & Jonas