Fall is the best season to explore New England. There’s nothing like the charming towns lined with colorful trees, apple cider mills and cozy inns with fireplaces to get you in the autumnal spirit. One of my favorite New England states to visit in the fall is Connecticut.
Not only is Connecticut a beautiful state, but it’s also the backdrop of one of the greatest fall vibe television shows of all time – Gilmore Girls. This guide outlines the best things to do and see on a Gilmore Girls Connecticut 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 my travel guide to Woodstock, Vermont and my complete travel guide to Salem, Massachusetts.
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, the creator of the television series, Amy 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 area perfect for a road trip. It’s easily accessible from New York City and once you’re there, all the destinations are within close range and it’s easy to do a Gilmore Girls inspired road trip.
How is Gilmore Girls and Stars Hollow connected to the fall season?
While the television show takes place over all seasons, there is a surge in Gilmore Girls popularity each fall. The show is nostalgic, as it was on the air from 2000-2007, and that’s when many of its fans first watched the series. Like many nostalgic things, the show is comforting and cozy, and fall is a good time to bask in those vibes.
The autumn season in general brings about a certain nostalgia. It’s a time of year for reflection, endings (summer) and beginnings (the new school year). The show also centers around a teen girl who is in school, Rory, who is very academic and many of the plot lines follow her school life.
Stars Hollow also shines in the fall months. Many of the show’s most popular episodes and scenes feature colorful foliage in town, arrays of pumpkins and warm cozy drinks – coffee is a staple on the show.
Fall is a great 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. This town is about a two and a half hour drive from New York City. If you have to fly for this trip, I recommend flying into New York City. There are three major airports that service New York City- John F. Kennedy, LaGuardia and Newark. Flights from every destination will arrive into one of these airports.
If you prefer to fly into Connecticut, you can look for flights into Bradley International Airport. This airport has fewer flights than the New York City based airports, but it’s the second-busiest airport in New England (after Boston). It’s located a little over one hour from Washington Depot.
If you fly into the area, a car rental is necessary for this Gilmore Girls experience. Many of the destinations are in suburban and rural areas and there is no public transportation that connects. You’ll be driving from various towns, farms and inns. Once you’re in this area each drive is less than an hour.
Gilmore Girls fall road trip in Connecticut – travel guide
While all of the destinations listed in this guide can be experienced in one day, you can also choose to spend the night. I recommend doing an overnight as you will be less rushed and ensure you hit all the Gilmore Girls spots. This guide will cover a two day and one night itinerary.
Day 1 – Gilmore Girls Connecticut fall road trip
Explore Washington Depot, Connecticut aka the real Stars Hollow
Washington Depot is the best place to start your Gilmore Girls trip. This is the town Stars Hollow is based on and you’ll immerse yourself immediately into the charming New England vibes.
This is a quaint small town and the streets lined with family-run businesses. You’ll notice similar shops here that are in Gilmore Girls – a cafe, a hardware store, a bookstore. On my visit to Washington Depot there were also many street signs and advertisements for local fairs and festivals that bring the community together. So very Stars Hollow!
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 group partaking in a knitting club!
The cafe has a robust coffee menu and I love trying their seasonal lattes. 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.
After you have your caffeine fix, walk around and explore Washington Depot. This is 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 hotel. This hotel is where Amy 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.
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 Gilmore Girls. While this is an expensive accommodation where nightly room rate typically exceed $1,000 in the autumn months, I do recommend booking it if you’re willing to splurge. If you prefer to sleep elsewhere, I recommend checking out one of the many airbnb accommodations in the area.
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 in 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 Taproom, the hotel’s casual restaurant.
Day 2 – Gilmore Girls Connecticut fall road trip
The Stars Hollow gazebo and apple cider
Begin day two of your Gilmore Girls road trip back in Washington Depot. Today you’re grabbing 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.
Drive about twenty minutes to the neighboring New Milford and visit their town green. Here you’ll find the iconic gazebo. Locals believe the New Milford gazebo inspired the one in Gilmore Girls that was highlighted in so many episodes. Soak in the small town charm and grab a photo in the gazebo.
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 and they have 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.
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. 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, it’s now the end of your Gilmore Girls fall road trip. 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.
Leave A Comment