Your Guide to the Ultimate 'Gilmore Girls'-Inspired Road Trip

If you grew up watching Gilmore Girls, Stars Hollow is a mythical place. The storybook home of Lorelai and Rory Gilmore embodies the cozy atmosphere of a small New England town where everyone knows everyone (and their business, too). For me, it was always more of a postcard than a destination, one that evokes a snow globe during the holidays and molten-hued foliage in the fall — until a recent trip to Washington, Connecticut, that is.

Beloved writer and showrunner Amy Sherman-Palladino — who is also the creative force behind The Marvelous Mrs. Maisel — actually came up with the idea for Gilmore Girls during a three-week stay at the Mayflower Inn in Washington.

“At the time I was there, it was beautiful, magical, and feeling of warmth and small-town camaraderie,” said Sherman-Palladino in a 2001 interview. "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, believe it. Stars Hollow exists — or at least, there’s a real-life place you can visit that will deliver all the Connecticut charm you'd expect from the hometown of your favorite mother-daughter TV duo. Read on for everything you need to know about the ultimate Gilmore Girls-inspired road trip.

How to Get There

Just a little more than a two-hour drive from New York City, the town of Washington is sandwiched firmly between the coast and the Hudson Valley, making it the perfect quiet enclave for a weekend getaway in the fall or winter. Driving is by far the best way to get there, as you’ll get to fulfill all your Stars Hollow fantasies as you watch the leaves changing, take in Christmas decor, and see fresh snow while you head out of New York City.

I invited a friend to accompany me and tapped Lincoln for a ride, driving the brand’s new Corsair car. If you, like me, don’t drive much and admittedly aren’t the best at directions (I take the subway every day, OK?), a car that offers comfort, navigation, and self-driving features is a godsend. The roads to Washington are well-worn, so we used the Lincoln BlueCruise tech, which assists with lane changes, speed, and in-lane repositioning almost the whole way there. It’s the sort of set-it-and-forget-it helper that makes a road trip that much easier — especially when you’re out of practice.

Where to Stay

If you’re in Washington for a Gilmore Girls moment, there’s really only one game in town: The Mayflower Inn & Spa. The historic site, which no doubt inspired Lorelai's fictional workplace, the Dragonfly Inn, dates back to the 1890s, when it was an all-boys school. Since it was restored in 1992, the property has added a spa, garden, guest accommodations, and an elevated decor sense that celebrates New England prep in all its glory. 

Even if you’re not a decor lover, the hotel’s Celerie Kemble-designed interiors will enchant you with its eclectic mix of modern whimsy and historic charm. Highlights include a fireplace-lit cushy library with dark wood detailing to curl up in with your favorite novel and a Shakespeare-inspired maze garden perfect for wandering and picture-taking.

What to Do

Not in the mood to leave the Mayflower? Take a quick stroll over to The Well, the hotel’s meticulously curated wellness center. This is not your average spa: The sprawling property (connected to the inn by a gorgeous tree-lined trail) offers everything and anything you could ask for from a relaxing retreat. Try a luxurious facial, go for a leisurely swim, or opt for a relaxing massage — this place truly has it all. You can even book a range of fitness classes, including restorative yoga and barre fusion. 

If you’re looking for more of an outdoor adventure, the hotel has electric bicycles with a guided course you can rent for an enchanting ride around Washington. Trust me; you don’t want to miss the old-school architecture, quaint shops, and breathtaking views Washington has to offer. It’ll feel like you walked (or rather, biked) onto the set of Stars Hollow.

Where to Eat and Drink

There’s no shortage of good food in Washington, but there are a few standouts. First, you have to stop by Marty’s Cafe for breakfast or coffee, because, to put it simply, it has big Luke’s Diner energy. Everyone here seems to know each other, the coffee flows freely, and the French toast is outstanding.

Next, you’ll want to grab a pastry or sandwich to refuel at The Pantry. If Sookie St. James opened her own place in Stars Hollow, this would be it. The local haunt has hearty soups, elegant sandwiches, and a host of hard-to-find gourmet pantry items to take home as a souvenir. 

Last but not least, dinner at the Mayflower is an event. Head to the Tap Room for some elevated, pub-style Connecticut comfort food and a craft cocktail (the espresso martinis are truly world-class) or try out the Garden Room for a fresh, seasonal dinner overlooking the hotel’s garden.