New Milford, CT

As promised two months ago in my Princeton Ivy League blog post, I have a bit of a surprise for Gilmore Girls fans; and yes, it does involve a gazebo.

More specifically, while on the last trip to New Haven, we took a small road trip and went up to New Milford.

New Milford | Connecticut |

Although it is widely known that the show is based on the town Washington Depot, the truth is that Amy Sherman-Palladino was inspired by many of the little towns in Connecticut to create Stars Hollow. After some research, I’ve decided that New Milford is the closest representation to the fictional town and I was not disappointed.

The drive up to Litchfield County was beautiful: winding and hilly road. We left right at sunset, so by the time we got to New Milford it was already dark. I’ve read some reviews of Stars Hollow fans being disappointed with New Milford in relation to Stars Hollow, but I found the towns to be quite similar.

New Milford | Connecticut |

New Milford | Connecticut |

New Milford | Connecticut |

Perhaps they expected to find a Luke’s Diner or Doose’s Market, but there were plenty of similar looking small stores; Bank Street Theatre and Bank Street Book Nook looked amazingly charming from outside. Unfortunately everything was already closed, even though it was a Saturday night. But just like Lorelai in Stars Hollow I stood in the middle of the main town street for 5 minutes with no cars passing. Had I been more brave, I would lay down on the pavement. And unlike the slightly more modern Stars Hollow in the Netflix revival, New Milford still has the charm of the old Stars Hollow and has not yet implemented parking meters!

New Milford | Connecticut |

I wish we had more time to spend in this charming town! On the way back to New Haven we actually drove through Washington Depot, and I am so glad we chose to stop in New Milford instead. Washington Depot was a lot more spread out and did not have the same small community feel. I am sure it is a charming town, but if you want a central green space, and come on, a gazebo, then I’d recommend visiting New Milford first!

New Milford | Connecticut |


  1. by Love Z on July 9, 2017  1:54 pm Reply

    Hey! Did you know that Susan Randel lives in New Milford? :-) I've always wanted to visit Susan and to see her town. Thanks for the great pictures!

    I don't know anything about Gilmore Girls, but that town looks super cute. Maybe I should watch the show.

    • by Iryna on July 10, 2017  9:02 pm Reply

      I did! It was a very impromptu road trip, so we didn't plan to meet. But I want to come back in the fall!

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