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Welcome to my blog. I document the planning and execution of my adventures. Have a nice stay!

My Favorite Things: Gilmore Girls Sites in Connecticut

My Favorite Things: Gilmore Girls Sites in Connecticut

If I could live in any fictional world, I will always pick Stars Hollow. Who doesn’t want to live in a small town with the quirkiest neighbors, the best bookshop and, of course, a diner with the perfect cup of coffee? Judging by the numerous internet articles listing all the ways to turn your Connecticut road trip into a passable recreation of Gilmore Girls, I don’t think I’m alone in my wishful thinking.

So, when I found myself in Connecticut with some time to spend between Hartford and New Haven, what better thing was there to do besides listen to Carole King on repeat and follow my own version of the Gilmore Girls roadtrip?


Every good Gilmore fan knows that no true homage to the show is complete without four things: a gazebo, an inn, a bookstore and a cup of coffee. I will admit that my trip only had three of the four because I don’t drink coffee in the afternoon, and yes, I know that Lorelai and Rory would be so disappointed in me for saying that. However, three out of four isn’t bad!

Nothing reminds me of Stars Hollow more than a wooden gazebo perched in a town square. It is the glue that holds our favorite town together – as is apparent in the shock expressed when Sookie dares to suggest that they move it for her wedding. (Thankfully, she is talked down by some tough love from Lorelai and Jackson.) The Gilmore aficionados online disagree about which small town Connecticut has the gazebo, but I say feel free to visit as many or as few as you like because it’s about the fundamental spirit of the gazebo, not a look-a-like competition. (Also, the fact that there are enough small town CT gazebos to sustain this argument is impressive in itself.) I chose the gazebo in New Milford. It may not look exactly like iconic Stars Hollow structure, but I wanted a gazebo to be my first stop and it seemed to be the closest to my chosen route. I don’t know if its charming nostalgia or plain gazebo magic or what, but standing in that wooden structure, I really did feel like I was in downtown Stars Hollow for a moment.

girlmore-girls-gazebo

 Although it does not have a gazebo, Washington Depot is the true pilgrimage point for any Gilmore fan. The show’s creator purportedly stayed at the Grace Mayflower Inn and was inspired to create the mother-daughter duo who anchor our beloved show. The Grace Mayflower still exists, and while it may only be affordable to the Emily Gilmores of the world, that did not stop me from taking a ride up their curvey and stone-lined driveway to get a look. However, disapproving looks from a staff member at the entrance left me with no outside pictures and no choice but to turn around. I guess they don’t appreciate Gilmore fans in Luke’s Diner t-shirts…

gilmore-girls-grace-mayflower

 Unlike the Mayflower Grace, the Hickory Stick Bookstore is happy to capitalize on their television relevance. While the store is far more cutesy than Andrew’s establishment, I appreciated their little corner of Gilmore themed items and overall selection of great books and gifts. A copy of Eat Like a Gilmore (the unofficial cookbook based on the show) was a necessary souvenir and the woman behind the counter wasn’t fazed by my obvious enthusiasm. There are probably worse customers than overly excited young women who are obsessed with books and small town Connecticut.

gilmore-girls-hickory-stick

Looking at all of the Gilmore roadtrips online is overwhelming and, if you combined them all together, it would probably take you a entire day to check off all the stops. However, as cliché as it seems, Stars Hollow isn’t a place, it’s a feeling. So whatever makes you want to talk fast, eat pie, and celebrate an obscure town event, that is your own personal Gilmore journey. Lorelai, Rory, and the rest of our favorite characters will always follow where you lead.

Road Trip Route: Connecticut Highlights

Road Trip Route: Connecticut Highlights

Stories from the Road: Cemetery of the Evergreens - New Lebanon, NY (December 23, 2017)

Stories from the Road: Cemetery of the Evergreens - New Lebanon, NY (December 23, 2017)