Connecticut? Count me in!
It’s an unwritten Lyssa Law, that if you are driving from Boston to NYC, you most pop into Washington Depot, CT. Andrea took me from one biz trip in Boston to a biz trip in NYC in 2015, and we fell deeply in love with the town that inspired Gilmore Girls and Stars Hollow. It was a glorious fall day, and Connecticut cemented a soft spot in my heart. I try to visit anytime I’m passing through and the third time was the charm this year! I finally timed it right to pop into the places that prompted the iconic haunts of the Hollow.
I’ve passed the signs for the Mark Twain house driving through Hartford, and I swear I can’t keep skipping it. It’s now the top of my list for my next trip. I didn’t realize it was designed by Louis Comfort Tiffany, but I read about it when researching that condo I told you about in Boston. It’s a stunner, so if you have time, you should definitely pre-book a tour. You will pass some gorgeous and glorious churches on your way into the quaint little town of Washington Depot. Some of its famous former residents are Conan O’Brien, Christine Baranski, James Taylor, Joan Rivers, and the now scandalized Scott Rudin.
Never one to shy away from bougie five star hotels, the Mayflower Inn is a magical must visit. It’s also where Gilmore Girls creator and show-runner Amy Sherman Paladino was inspired to write the story. She sat at a table by the fire in the pub and started scribbling ideas about a single mom and her daughter in a charming New England town. I was enchanted by my pumpkin creme brulee served in a pumpkin, and the new “Too Tired to Sleep” art installation in the library. It’s a lovely walk through the Shakespeare Garden, and I’m pretty sure the prettiest wallpaper collection on the East Coast. Andrea and I regularly daydream about a special spa trip here someday. Until then, it was a perfect place to pull over and knock out some work as I headed towards PA for the next leg of my adventure.
Washington Depot tried to make it easy on fans and created this handy Gilmore Guide, this one encompasses the sister villages too. The town is tiny, it won’t be hard to find your Luke’s Diner, Doose’s Market, Stars Hollow Books, and Town Hall and Town Square. Five Janes, a sweet boutique, embraced the Gilmore Fandom and sells some Stars Hollow swag.
It was a great little field trip and a nice way to break up the drive to the city. We passed a couple of beautiful cemeteries with a cloak of fallen leaves. One overlook was vaguely familiar, and reminded us of the opening credits. It was a little creepy to look down and see my name on the headstone as I was taking that last photo.
Even if you don’t have any particular affinity for Gilmore Girls, this is a charming part of Connecticut and at least worth a lunch stop :) You can pretty much see it all in under an hour, and then head to the Mayflower Inn for a nice lunch and walk. If you want a more immersive field trip, there’s always the Gilmore Girls Fan Festival. Though I haven’t gone to the festival, I HAVE done the Warner Bros. Gilmore Girls Christmas event and it is AMAZING. The WB studio tour is by far the best one in LA, and we had so much fun surprising my sister with a trip to see the Friends and GG sets for her birthday. We give very enthusiastic thumbs up.
