This blog post was updated with the latest information in August 2026
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Washington Depot, CT
Fall is one of the best times to explore New England, and Connecticut is an especially magical destination in autumn. Picture charming small towns lined with colorful fall foliage, cozy cafes serving delicious pumpkin spice lattes, historic inns, apple orchards with the best cider donuts and quaint covered bridges. If you’re looking for a quintessential New England fall road trip, Connecticut has all the ingredients.
But there’s another reason Connecticut is particularly perfect for a fall getaway: it has the perfect Gilmore Girls aesthetic in the fall.
The beloved television series is synonymous with fall. This is mostly thanks to its bucolic small town setting in a fictional town called Stars Hollow, with changing leaves to a focus on cozy coffee runs, charming shops and idyllic New England scenery. While Stars Hollow, Connecticut, is fictional, the show’s creator, Amy Sherman-Palladino, drew inspiration from real Connecticut towns when creating the world of Stars Hollow. And you can visit these towns!
This Gilmore Girls Connecticut road trip takes you to some of the real life places that inspired the show and its fictional hometown. From picturesque Connecticut towns and historic landmarks to cozy cafes, coffee shops, hotels and local stores, these destinations offer a chance to experience the real life Stars Hollow for yourself.
Whether you’re a lifelong Gilmore Girls fan or simply looking for the best fall towns in Connecticut, this guide will help you plan a cozy autumn road trip through some of the state’s most charming destinations. Pack your best Rory Gilmore sweater, grab a cup of coffee and get ready to explore Connecticut in the fall, Gilmore Girls style.
What is Gilmore Girls?
Gilmore Girls is an American comedy drama television series that ran in the early 2000’s. The show takes place in an idyllic Connecticut town, the fictional “Stars Hollow,” and follows the relationship between a young single mother, Lorelai Gilmore, and her teen daughter, Rory Gilmore.
While the majority of Gilmore Girls was filmed on a studio in California, Sherman-Palladino has said that Stars Hollow was inspired by the very real town of Washington Depot, Connecticut and its surrounding area of Litchfield County.
This part of Connecticut is perfect for a road trip. It’s easily accessible from both New York City and Boston, and many of the destinations are within relatively close driving distance of one another. A Gilmore Girls-inspired road trip through Connecticut makes it easy to explore the charming towns, cafes, shops and landmarks that evoke the world of Stars Hollow.
Litchfield County, CT
Why take a Gilmore Girls fall road trip?
If you’re interested in other fall road trip guides, check out my 7 day in New England road trip itinerary. If you’d like more specifics on the destinations I mentioned, here is a travel guide to Woodstock, Vermont, a day trip guide to Salem, Massachusetts and my complete travel guide to Salem, Massachusetts.
How is Gilmore Girls and Stars Hollow connected to the fall season?
While Gilmore Girls takes place throughout all four seasons, there is a surge in the show’s popularity each fall. The series is nostalgic for many fans who grew up watching it during its original run from 2000 to 2007. Like many nostalgic things, the show feels comforting and cozy, and fall is the perfect season to bask in those vibes.
Autumn itself also brings a certain sense of nostalgia. It’s a season of reflection, endings and new beginnings, from the transition out of summer to the start of a new school year. The show centers around Rory, a highly academic teenager, and many of its storylines follow her school life and ambitions.
Stars Hollow also shines in the fall. Many of the show’s most memorable scenes feature colorful foliage, pumpkins, cozy drinks and, of course, plenty of coffee, which is a staple of the series.
Fall is the perfect time to step into the charm of Rory and Lorelai’s hometown and embark on a Gilmore Girls-inspired road trip through Connecticut.
Traveling to Connecticut for your Gilmore Girls trip
Your Gilmore Girls Connecticut fall road trip will be centered around the town of Washington Depot, Connecticut, which is about a two-and-a-half-hour drive from New York City.
If you’re flying in for this trip, New York City is one of the best options. The city is served by three major airports, John F. Kennedy International Airport (JFK), LaGuardia Airport (LGA) and Newark Liberty International Airport (EWR), with flights arriving from destinations across the country and around the world.
If you’d prefer to fly directly into Connecticut, you can also look for flights to Bradley International Airport (BDL) in Windsor Locks. Bradley has fewer flights than the New York City airports, but it’s the second-busiest airport in New England after Boston Logan International Airport. It’s located a little over an hour’s drive from Washington Depot.
Boston is another option, although it’s about a three-hour drive from Washington Depot, making it less convenient than flying into New York City or Bradley International Airport.
Do You Need a Car for a Gilmore Girls Road Trip?
Yes! A rental car is necessary for this Gilmore Girls road trip. Many of the towns, farms, shops and inns featured throughout this guide are located in suburban and rural areas without public transportation connecting them. You can easily book an affordable car rental here.
Once you’re in the area, getting between destinations is relatively easy, with most drives taking less than an hour. Having a car also gives you the flexibility to explore the winding country roads and stop at scenic spots, farm stands and other small-town destinations along the way.
A Real Life Gilmore Girls Connecticut Fall Road Trip- Travel Guide
While all of the destinations in this guide can be visited in a single day, I recommend spending one night in the area. An overnight stay gives you more time to explore without feeling rushed and ensures that you can experience all of the Gilmore Girls-inspired spots at a leisurely pace. This guide outlines a two-day, one-night itinerary.
Day 1 – Gilmore Girls Connecticut fall road trip
Explore Washington Depot, Connecticut: The inspiration for Stars Hollow
Washington Depot is the perfect place to start your Gilmore Girls trip. This charming Litchfield County town is widely recognized as one of the real-life inspirations for Stars Hollow.
This is a quaint small town with streets lined with family-run businesses. You’ll find several shops and businesses that evoke the world of Gilmore Girls, including a cozy café, an independent bookstore and a classic hardware store. On my visit to Washington Depot there were also many street signs and advertisements for local fairs and festivals that bring the community together. This is very Stars Hollow!
Start with coffee at Marty’s Cafe
I recommend arriving in the morning and starting your day at Marty’s Cafe. This is the cafe that inspired Luke’s, the bustling diner the main characters frequent for coffee in Gilmore Girls. Marty’s is a busy neighborhood cafe where it seems like everyone knows everyone and the baristas always remember your order. The staff is friendly and the cafe is light and airy, full of windows and cozy tables and chairs. I loved watching the locals greet each other. I even saw a knitting club taking place at Marty’s!
The cafe has a robust coffee menu and I love trying their seasonal lattes. On my most recent visit, I had a toffee pecan latte that was the perfect fall coffee to fuel up for a day of sightseeing. Marty’s also has a bakery with delicious pastries and a big menu serving breakfast and lunch staples – egg dishes, sandwiches and salads. I usually order a salad or a veggie sandwich. And you can’t miss one of their homemade cookies.
The Hickory Stick Bookshop
Explore Washington Depot’s Shops
After you have your caffeine fix, walk around and explore Washington Depot. It’s a not a big town, but it is big on charm.
Visit The Hickory Stick Bookshop, which is the inspiration behind Stars Hollow Books. This has been Washington Depot’s independent bookstore for over 70 years. You’ll find a huge selection of books covering all genres, gifts and there’s even a Gilmore Girls section with books and mementos related to the show.
Five Janes boutique is a women’s clothing store in town. Head here to pick out a Rory Gilmore-worthy sweater. In addition to clothing the boutique also sells Gilmore Girls trinkets, like a Luke’s coffee mug and Stars Hollow magnet. The casual preppy styles found in Five Janes could easily be part of Rory’s wardrobe.
Other stores to visit include Stuart’s Floral, a flower design store that also sells souvenirs and gifts, Washington Food Market which has been open for over 100 years and is the inspiration behind Doose’s Market, and Washington Supply Co, quite possibly the most charming hardware store and the inspiration behind Williams Hardware.
Evening at “The Independence Inn”
After a day spent walking around Washington, Depot, it’s time for some relaxation. Hop in the car and drive five minutes up the road to The Mayflower Inn & Spa, a luxury resort hotel. This hotel is where Sherman-Palladino stayed while she was in Connecticut working on developing the show. It is said to be the inspiration behind The Independence Inn, where Lorelai worked in Gilmore Girls.
The Mayflower Inn & Spa is nestled on 58-acres of beautiful gardens and wilderness. The property exudes New England charm and has an upscale and elegant yet homey feel. It has the same colonial aesthetic as the inn from the show. While this is an expensive accommodation where the nightly room rate typically exceed $1,000 in the autumn months, I do recommend booking it if you’re willing to splurge.
Another hotel I like in the area is called The Abner. It’s in Litchfield, which is about a 20 minute drive from Washington Depot. The Abner Hotel is a luxury boutique hotel in a restored historic courthouse. It’s decorated beautifully and is located on a main street, walkable to many shops and restaurants.
Whether you stay overnight at The Mayflower Inn or not, a visit to the property is a must. Explore the gardens and admire the grounds. If you’re in the mood for some relaxation, non-hotel guests can enjoy a meal at the hotel or a service in the spa, The Well. I’ve had a hot stone massage at The Well before and it was a great experience. You can also have dinner in The Tap Room, the hotel’s casual restaurant that was created with the aesthetic of a New England tavern. If you prefer to eat in town, I really like dining at G.W. Tavern, a cozy restaurant in Washington Depot that dates back to the 1850s and has a fireplace.
Day 2 – Gilmore Girls Connecticut fall road trip
Stars Hollow Gilmore Girls gazebo in New Milford, CT
Visit the Stars Hollow gazebo and grab some apple cider
Begin day two of your Gilmore Girls road trip back in Washington Depot. Start your day with coffee and a pastry at The Pantry, a bakery that’s reminiscent of Stars Hollows’ Weston’s. I opted for a croissant and a coffee to start my second day in Stars Hollow.
New Milford and the Stars Hollow gazebo
From Washington Depot, drive about 20 minutes to neighboring New Milford, Connecticut, and visit the town green. This is where you’ll find the iconic gazebo that many Gilmore Girls fans believe inspired the gazebo in Stars Hollow, which was featured in numerous episodes throughout the series. In the fall, the town decorates the gazebo with pumpkins and mums and cornstalks. It’s an incredible photo stop! This is one of the best stops on this Gilmore Girls-inspired Connecticut road trip, especially in the fall when the gazebo is decorated and the surrounding trees turn orange and yellow.
You can also walk around the shops in New Milford that line the town green. You’ll find some gift shops selling Gilmore Girls merchandise, an independent bookstore and tea shop called Honeybee Books & Tea and a very fall-vibes gothic inspired coffee shop called Raven’s Bakehouse.
Visit a Connecticut cider mill
One of the most iconic fall episodes of Gilmore Girls centers around the opening day of the local cider mill and a cider mill parade. Leaning into this autumn fun, I suggest you visit a couple of Connecticut’s best local cider mills.
Hogan’s is one of Connecticut’s most popular cider mills. It’s located about 45 minutes away from New Milford. Hogan’s has been pressing cider since 1912. They offer a farm shop and a tasting room for guests to experience their regular and hard apple cider. The mill is also known for their fun and festive drinks, like “The Drunken Donut,” which is a cider drink topped with an apple cider donut, whipped cream and autumn sprinkles. You can choose to order it with or without alcohol.
Park Lane Cider Mill
After Hogan’s, you can visit another local cider mill. Park Lane Cider Mill is located back in New Milford and has an older more vintage feel. There isn’t as much to do at this cider mill as there is at Hogan’s, but it’s worth the visit to check out their small store, try their cider and grab a donut. After Park Lane, you can stop by Averill Farm which is located just up the road. This farm has been open since 1746. The 260-acre farm primarily grows fruit and offers pick-your-own apples in the fall season. They also sell delicious apple cider donuts.
With your belly full of apple cider and donuts, your Gilmore Girls fall road trip has officially come to an end. It’s easy to see the inspiration for Gilmore Girls when you visit this quaint area of Connecticut. With its small-town charm and pastoral views it seems exactly like Stars Hollow. You can almost expect to run into Rory and Lorelai walking down the street, coffee and cider in hand.
If you want to extend your trip and explore more of New England in the fall, here is my robust New England fall road trip travel guide that covers Vermont, Salem and New Hampshire.
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