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
- There’s a gazebo! Hallelujah!
- Town green – though way bigger than Stars Hollow.
- Church adjacent to town green – though it’s made of stone and not white.
- There is a nearby boarding school that looks like “Chilton.”
Major Differences from Stars Hollow
- It’s more like a street and not a cozy/intimate square like in Stars Hollow.
- Not many charming shops…more like abandoned spaces and realty businesses.
- 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!