The Real Stars Hollow and Amy Sherman-Palladino
Many years ago, Amy Sherman-Palladino took a trip through Litchfield County in Connecticut and fell in love with it's New England charm: "
At the time I was there, it was beautiful, it was magical, and it was feeling of warmth and small-town camaraderie. . . . There was a longing for that in my own life, and I thought – that's something that I would really love to put out there." So she began to write this incredibly witty story about Lorelai Gilmore and her teenager daughter "Rory" Lorelai Gilmore II - the story we came to know as Gilmore Girls that aired from 2000-2007 and recently made it's debut on Netflix (Yay!)
When asked in an interview where exactly Stars Hollow is based off of, Amy responded by saying that primarily her inspiration came from Litchfield County; but was really a melting pot of ideas she had formed in her head. The execution of these ideas on the backlot of Warner Brothers's set in California was primarily influenced by Sherman-Palladino's desire for it to be as authentic as possible. So today, I want to share with you the towns that inspired/influenced Stars Hollow in my opinion.
Washington Depot
Often believed to be the central inspiration for Stars Hollow, Washington Depot is a town with a population of 3,578, as of the 2010 census and is best known for it's history and architecture. While typically said to be "not much to look at," Washington is home to Marty's Cafe, boutique stores like Liberty Lemonade and Averill farm., as well as the inspiration for the Dragonfly Inn featured in Gilmore Girls. Known to locals as the elaborate Mayflower Grace Inn.

Wallingford
Wallingford in New Haven, Connecticut according to the 2010 census has a population of 45,135 residence. However, Wallingford Centre (the CBD) is home to 18,210 people. The town sits alongside the Quinnipiac River, where it features sprawling vineyards and period homes. Choate Rosemary Hall established in 1890 is the elite preschool in the Wallingford district; also said to be bigger than most college campuses. They even have their own bowling alley! Choate Rosemary Hall is believed to be what inspired Sherman-Palladino's Chilton Preparatory School. They also hold fun events like "Twilight Tunes"in the CBD.
New Milford
Above: New Milford Town Green (by Thomas Schoeller)
New Milford is arguably the town I feel most embodies Stars Hollow. The streets are adorned in fairy lights, they have a big white church, a lovely gazebo, they even have Theo's Downton Diner - you get the picture! There main street is also adorned with American flags and sweet boutiques. As of 2010, the population had reached 28,142. The town itself is located in Litchfield County and is 14 miles north of Danbury. The also hold quirky events like "vinyl nights," "icecream socials" and a "Star Wars display. New Milford also has an elite prep school in Canterbury School.
Litchfield
Despite being more built-up than the other inspirational towns in the line up, Litchfield, Conneticut which was actually mentioned during the series (Luke buys an apartment there,) does certainly have a somewhat Gilmore Girls feel to it. Like many New England towns, Litchfield features a white church, a village green and an abundance of eateries and shops. According to TripAdvisor, the most popular thing to do while in the town of Litchfield is visiting the White Memorial Conservative Center.

Guilford
Guilford in New Haven County, Connecticut and has a population of 22, 375. Guilford is probably one of the most walkable towns featured in this masterpost. The village green is incredibly large and across from that - you guess it! - there is a big white church. Guilford's main street feels quite intimate though as there are a number of small shops, boutiques and even the Guilford Food Center; somewhat reminiscent of Doose's Market. Funnily enough there's even a Dance Studio!