Plan a fall getaway in Washington, Connecticut inspired by Gilmore Girls’ Stars Hollow.

Published
Memorial Town Hall, Washngton, Connecticut

Destinations United States

 Nicole Findlay



Colorful leaves, colder temperatures, and earlier evenings can only mean one thing — fall has officially arrived. It’s time to cozy up in sweaters, sip on pumpkin-spiced lattes, and indulge in re-watching episodes of “Gilmore Girls.” The show, which originally premiered on October 5, 2000, has a distinct autumnal feel that goes beyond Lorelei’s love for hot coffee, the abundance of comfort food consumed by the mother-daughter duo, or Rory’s experiences at Chilton and Yale.

Stars Hollow, the fictional town where Lorelei and Rory reside in “Gilmore Girls,” exudes a fall aesthetic. With its variety of autumn activities and the cozy attire worn by its residents, Stars Hollow holds a special place in the hearts of many fans. While Stars Hollow may not exist in reality, you can plan a perfect fall getaway to Washington, Connecticut, which served as the inspiration for the town in the show.

Washington, Connecticut, known as one of the most beautiful places in the northeast, captures the charming and warm small-town ambiance of Stars Hollow. It boasts a similar town square, delightful local diners, and, of course, a bookstore. Moreover, it is easily accessible and offers numerous enjoyable activities to partake in.

Things to do in Washington, Connecticut

Hiker in Washington, Connecticut



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While “Gilmore Girls” fans visiting Washington, Connecticut, will likely want to enjoy a leisurely walk through the historic small town, grab a cup of coffee at a local diner, and browse a bookstore, there is much more to do, especially in the fall. With several state parks nearby, perfect to see seasonal foliage, visitors have a variety of hiking and biking trails to choose from. In fact, Connecticut offers some of the best hiking in the country. 

Additionally, there are numerous gardens and farms to explore, as well as a couple of vineyards. The award-winning Hopkins Vineyard and Spring Hill Vineyards are fun options, both in beautiful settings. Visitors may also enjoy stepping out of the crisp fall air and into the warmth of two museums in Washington, Connecticut: the Gunn Historical Museum and the Institute for American Indian Studies. Museumgoers can channel their inner Rory Gilmore and learn something new.

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Washington, Connecticut, also boasts a selection of boutique shops, such as the Hickory Stick Bookshop, as well as a variety of restaurants and bars. Even if you’re not a fan of the show, a trip to Washington is well worth it. For those seeking a Luke’s Diner-like experience, a local favorite is Marty’s Café, which serves delicious traditional breakfasts, burgers, and, of course, coffee.

How to get there and where to stay

State park in Washington, Connecticut

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The New England town of Washington is easy to get to. If traveling by car, visitors can enjoy quiet country roads, and it’s less than two hours from New York City. For those planning to fly, there are several options. Passengers can choose to fly into Danbury Municipal Airport (26 miles), Bradley International Airport (51 miles), or Westchester Airport (57 miles).

While Washington offers many fantastic accommodations, fans of “Gilmore Girls” should consider staying at the Mayflower Inn & Spa. The average rates are $1,800 per night with a 2-night minimum stay. Although a bit fancier than the Dragonfly Inn, “Gilmore Girls” creator Amy Sherman-Palladino got the idea for the show while staying at the Mayflower Inn & Spa. She told the Harford Courant that while there, she “fell in love with Connecticut over a two-day period — crazy in love!” It’s no surprise why, as Washington is a charming town and the Mayflower Inn & Spa is an elegant retreat situated on 58 acres of land. It offers restorative spa treatments, on-site restaurants, tennis courts, a swimming pool, and beautiful gardens.

Other accommodation options in Washington include the peaceful Windemere Bed and Breakfast ($160 per night) and the Hopkins Inn (approximately $140 to $245 per night). The latter, which has been open since 1847, is located on a hillside overlooking Lake Waramaug.

Dave Pennells

By Dave Pennells

Dave Pennells, MS, has contributed his expertise as a career consultant and training specialist across various fields for over 15 years. At City University of Seattle, he offers personal career counseling and conducts workshops focused on practical job search techniques, resume creation, and interview skills. With a Master of Science in Counseling, Pennells specializes in career consulting, conducting career assessments, guiding career transitions, and providing outplacement services. Her professional experience spans multiple sectors, including banking, retail, airlines, non-profit organizations, and the aerospace industry. Additionally, since 2001, he has been actively involved with the Career Development Association of Australia.