Photographing A Gilmore Girls Road Trip through Connecticut (And Beyond!)

Share on Social Media!

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 vacation into a Gilmore Girls road trip, 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 photograph my own version of the Gilmore Girls road trip?

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, but I found a way to incorporate the fourth no matter where you live. Instead of trying to find Luke’s Diner, read until the end to see how you can bring Luke’s to you!

Gilmore Girls Road Trip – Gazebo

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 standing in that wooden structure, I really did feel like I was in downtown Stars Hollow for a moment.

Photo Tip – Make sure to get some of the background in the shot for a context. Having the grass and the houses in the background helped to give you the small town feel that we are going for with this photo!

Gilmore Girls Road Trip – An Inn

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…

Photo tip – The sign by the road is probably your best bet for a photo without inconveniencing anyone at the actual hotel. Snap a quick photo, be polite, and you can cross it off your list! (of course, there’s also the option for you to stay at a charming B&B somewhere in the area and make that your Inn photo opp. Lorelai would certainly be proud!)

Gilmore Girls Road Trip – Bookstore

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.

Photo Tip – I’m not sure how they would feel about someone actually taking photos in the store and, after the unfriendly vibe at the Grace Mayflower, I didn’t feel like pushing my luck. However, a much better photo opportunity would be inside the store, either in their Gilmore corner and just amongst the stacks. (Bonus points if you can find a Pushkin book and pretend to smell it.)

Gilmore Girls Road Trip – Coffee

Without coffee, there is no Gilmore Girls, we all know that. So where do you get the perfect cup to cap off your road trip through fake Stars Hollow, Connecticut? While there are plenty of diners and cafes in these small towns, I think we can do better than a cup in any old diner or cafe.

How about coffee from the man himself? The one and (always) surly, Luke Danes.

You may or may not know that Luke’s true alter ego (and actor) Scott Patterson actually has his own coffee company, so now we all have a Luke’s Diner option that it isn’t location dependent. Let Luke’s come to you!

(Note this post isn’t sponsored. I bought the coffee with my own hard earned cash and I don’t get any commission for you clicking on the link or buying.)

In true Gilmore Girls style, I ordered a box of Scotty’s French Roast KCups for my mom and I to try together. If you (like me) were worried that a french roast would be too much for your weak coffee palate, never fear! Both mom (who drinks her coffee very strong and very black) and me (who likes a more mild roast with creamer) enjoyed it. Like the show, this coffee brings people together to enjoy some quality time together.

No matter how far away Connecticut is from you, a cup of Luke’s coffee is only a few shipping days away. (And you don’t have to worry about him telling you to put your cell phone away!)

Photo tip – Obviously there a million ways to take a cute photo with a cup of coffee. I recommend doing it with someone you love! (Thanks mom for playing along!)

Gilmore Girls Road Trip – Conclusion

Looking at all of the Gilmore Girls road trip itineraries 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.