New Milford, CT vs Stars Hollow

Yes, there is a gazebo, but…

Along with Washington, CT, New Milford has been touted many times on Gilmore Girl fan blogs and forums as one of the towns in Connecticut that most closely resembles Stars Hollow. One former New Milford resident even said that after she watched an episode of the Gilmore Girls, she actually believed the show was filmed there! Naturally, after seeing photos of the promising gazebo (a Stars Hollow staple!), New Milford was among the top must-see towns on my list that I had to visit on my quest to finding Stars Hollow.

…is that all there is?

Honestly, I was a bit skeptical about this town after doing some recon on Google Maps. After taking a peek of the town green through Google Maps Street View, I thought the main street looked a bit weathered and didn’t seem to have many charming/quaint shops and thriving businesses that would serve an isolated community similar to Stars Hollow. After visiting the area firsthand, my suspicions were sadly confirmed.
Don’t get me wrong, the gazebo is wonderful…. And when the town is covered in fresh snow (as seen in my video), New Milford definitely has its own charm – but it’s no Stars Hollow. After seeing some of the abandoned businesses and lack of foot traffic, the area felt kind of…depressing. When I’m supposedly in the heart of a town, I want to bask in its isolation, as if it’s “hugging” me (similar to how Lorelai explains that the library at the Dragonfly Inn is her favorite room because it “hugs you” in a way that makes you feel safe, warm and loved). I couldn’t help but feel like I needed a blanket when walking around New Milford, and believe me, it had nothing to do with the chilly weather that day.

But wait…I found “Chilton”

After exploring the town green by foot, we drove around the neighborhood and spotted a very charming private school that was definitely reminiscent of Chilton, right down to the color of their uniforms! Despite my earlier disappointment regarding the neglected town green, the beautiful campus of Canterbury somehow makes up for it. So, if it’s Stars Hollow you seek, you may find a very thin slice of it in New Milford, CT after all.

Similarities to Stars Hollow

  1. There’s a gazebo! Hallelujah!
  2. Town green – though way bigger than Stars Hollow.
  3. Church adjacent to town green – though it’s made of stone and not white.
  4. There is a nearby boarding school that looks like “Chilton.”

Major Differences from Stars Hollow

  1. It’s more like a street and not a cozy/intimate square like in Stars Hollow.
  2. Not many charming shops…more like abandoned spaces and realty businesses.
  3. Lack of foot traffic – not many locals milling around and enjoying leisure activities/running errands, etc.


About my quest – see my video footage of New Milford and other towns that look like Stars Hollow!

I’ve been obsessed with the quirky town of Stars Hollow for years now, and did some research online to see which towns resembled it the most. I scoured blogs, articles and forums, taking notes from real Connecticut residents and other Gilmore Girls fans, who were also on a similar quest. Then, I narrowed down a comprehensive list of the top towns to visit on my journey to finding a real-life version of Stars Hollow. See the video of my journey above!

3 comments

  1. Pami says:

    Look up Safety Harbor, FL :)) That’s my Stars Hollow! There’s a gazebo, always events going on, main street with foot traffic, small shops, etc.

  2. Local says:

    I’m from the area (Washington to be specific) and honestly I disagree. There’s a ton of foot traffic especially nights and weekends, as far as small shops go theres the small olive oil store on the green where they always remeber me and my father, bank street theater which has a great small theater feeling, Alpenhaus is a great restaurant with a bar in the second floor (trivia night is so fun and the bartender is a great guy), for Luke’s you’ll never get that feeling in a diner as an out of towner but there are a ton of places in the area that if you go to you get that feeling for me Jackie in bantam, 3 brothers in new milford and, cafe on the green in Washington can all give me that lukes vibe its different for everyone, also small bakeries like sweet spot and the semi questionable Chinese places like new Main moon feel like they’re right up Lorelei and Rory’s alley, there’s often events in the town its just the town is bigger than Stars Hollow and fairs occur all over with people from all towns attending examples like village fair days in New Milford or the Bridgewater fair which is like a 10 minute drive from new milford green at most, theres concerts by local bands in the gazebo quite often too, then theres all the little things that arent in Stars Hallow that give New Milfird a unique feel like the craft fair in the old railroad station, the elephants trunk flea market which is sensational by the way you can always find some really cool stuff (also stop at daves doughnuts while you’re there because they’re delicious) or the memorial day parade whose new milford I go to every year. Then the atmosphere of the green I also disagree on as bank street and tbe green always give of the feeling you get when you would see Rory and Lane walking through the square talking about nothing just being high school friends or a young couple can be seen on a first date there just about any given night. I will admit when you wrote this its possible it wasn’t the same as over the last couple of years they’ve done a ton of renovation that have brought the town greater life but if you were to revisit and have a local with you especially in august when theres 2 fairs in the area every week you’d be able to see it in a different light I think. Any town can get the Stars Hallow feel if you’re there enough time to take ot in because what made the show great was everything felt familiar to you because it was familiar to Lorelei and Rory the two people we experienced it through.

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