Curator’s statement
During the early days of the pandemic, while we were all hunkered down and staying safe, my mom and I found solace in binge-watching Gilmore Girls. We were captivated by the heartwarming mother-daughter bond and the charming, picturesque world of Stars Hollow. Once we could safely venture out, we decided to create our own adventure inspired by the show—a self-guided Gilmore Girls road trip through Connecticut. As we set out on our journey, we discovered that the inspiration for Stars Hollow was sourced from multiple towns in Connecticut, each offering its own unique charm and connections to the beloved show. Here’s a detailed guide to the highlights of our road trip, including must-see locations, hidden gems and tips for capturing that quintessential Gilmore Girls experience.
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Things to do in Connecticut
Washington Depot
Washington Depot is said to have been the main source of inspiration for Stars Hollow, with their own versions of Luke’s Diner (Marty’s Cafe), Dragonfly Inn (The Mayflower Grace) and Doose’s Market (Washington Food Market)! Although not exact replicas, each location brings its own sense of small-town charm and community. The quaint community is nestled in the mountains and is a perfect place to take a leisurely stroll while sipping your coffee coffee coffee!
Not everyone can drink coffee like Lorelai Gilmore, though. If you want to swap out your caffeine for some wine, visit Hopkins Vineyard, where you will find an excellent selection of wines, food and atmosphere.
New Milford
Drive on over to Washington Depot’s neighbor and you’ll discover even more Stars Hollow inspiration. Namely, the town gazebo! You can also visit Bank Street Book Nook, said to be the blueprint for Stars Hollow Books and Ms. Patty’s Dance Studio (called the Pavilion Hall in real life!). With its mix of boutique shops, charming cafes and historic architecture, New Milford immerses you in its vibrant, small-town atmosphere as soon as you step foot in town.
You can also take inspiration from Emily Gilmore and join New Milford’s Antique Trail. Be careful though, if these stores are anything like Kim’s Antiques, they will have a you break it, you buy it policy!
New Haven
As any fan will be aware, New Haven is home to Yale University, where Rory Gilmore attended college! The campus is a beautiful area to walk around and take in some history. Established in 1701, Yale is one of the oldest universities in America. Visit the Yale Peabody Museum of Natural History and discover exhibits on dinosaurs, ancient civilizations and natural history, or stop by Rory’s freshman dorm, Branford College.
Yale and New Haven, by extension, is also known for its thin-crust, brick-oven pizzas with lots of char. There are a number of pizza joints on campus where you can try the legendary pizza for yourself. We visited BAR on our trip, but Frank Pepe Pizzeria Napoletana is the most famous!
Although we never see Rory visit the coast in the show, New Haven is just north of a beautiful shoreline that you shouldn’t miss out on! West Haven offers picturesque seaside towns, scenic boardwalks, fresh seafood and beautiful lighthouses.
Whether you're a die-hard fan or just looking for a picturesque fall getaway, these insights will help you make the most of your own New England adventure, with maybe a little more planning than Lorelai, post-Max breakup!
Places to eat & drink in Connecticut
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This guide is part of our ongoing series on travel to Connecticut. Looking for more travel inspiration? Check out my guide, Discovering the Concrete Jungle: A Modern Explorer's Guide to New York City.