Stephanie Hallett
November 02, 2016 4:32 pm

We’re officially less than 25 days away from the Gilmore Girls revival on Netflix (OMG! GET THE POP TARTS!) so we think now is the perfect time to take a little spontaneous Gilmore Girls-inspired road trip, don’t you?

While Stars Hollow, Connecticut isn’t actually on the map — it’s inspired by the small Connecticut town of Washington Depot — the show’s creator, Amy Sherman-Palladino, drew plenty of inspiration from real-life communities, inns, and landmarks when she imagined the show.

So, in the spirit of the new Gilmore Girls, we present to you a guide (thanks to some help from to experiencing Rory and Lorelai’s reality — complete with tons of caffeine and junk food — on a tour through some of Connecticut’s most picturesque small towns: Guildford; Litchfield; Washington Depot; New Milford; and Kent.

Don’t forget to snap (and send!) photos!

First stop: Guilford

Stock up on chocolate on the first stop of your Gilmore Girls road trip. Guilford boasts a shop called The Village Chocolatier that looks so much like Taylor’s Old Fashioned Soda Shoppe, we kind of can’t get over it.

Once you’re satiated, pop into Breakwater Books and browse the aisles for hours, just like Rory would.

At night, lay your head at the Tower Inn and Suites of Guilford/Madison — you’ll need to be well-rested for your glorious adventure tomorrow.

Next up: Litchfield

Channel your inner Mrs. Kim or Emily Gilmore at Bradford House Antiques & Lawrence Jeffrey Jewelers  in Litchfield, where you’ll find all the jewelry, art, and antiques your heart desires.

After you’ve worked up an appetite shopping, stop in at West Street Grill for a fancy schmancy dinner — ideal for a date like the one where Christopher proposed to Lorelai in Paris (except you won’t have to go all the way to France!)

Finally, spend the night at The Litchfield Inn (and we promise, this Litchfield has nothing to do with the prison on Orange Is the New Black).

Onward to: Washington Depot

You’ve finally arrived at the #1 site of Gilmore Girls inspiration. In this town, you’ll definitely want to stop by Washington Food Market and imagine yourself browsing the aisles at Doose’s.

Your most important stop in Stars Hollow — oops we mean Washington Depot — will be The Mayflower Grace. While Sherman-Palladino was on vacation in Connecticut, it was during her stay at this hotel that the inspiration for Gilmore Girls came to her. If this gorgeous establishment feels familiar, it’s because she modeled the Independence Inn after it.


Next up: New Milford

Get ready to be charmed by this gorgeous little hamlet — when you stop by the town gazebo, you’ll really feel like you’ve entered Stars Hollow.

Once you’ve had enough people watching in the center of town, hit up Theo’s Downtown Diner for tons of coffee and a breakfast of pancakes and donuts. Don’t be surprised if you think you’re at Luke’s!

At night, rest your head at the Homestead Inn, which bears an uncanny resemblance to the Dragonfly.

Last stop: Kent

You’ve had an amazing time so far, right? Well, the fun’s not over. Stop by Black Sheep Yarns in Kent to pick up the supplies you’ll need to host a knit-a-thon when you get home (because duh).

And on the final night of your tour, stay at the Cornwall Inn — another charming abode where you’ll feel just like a guest at the Dragonfly.

We hope this trip made you feel like a Gilmore girl, and we can’t wait to talk all about Gilmore Girls: A Year in the Life with you after Thanksgiving!