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Gilmore Girls Road Trip in Connecticut
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Naomi Liz Figueroa
Everything you need if you're dreaming of a Gilmore Girls Trip (from a CT local)!
Map
Sections
3
 
Itinerary
 
Places to Visit
 
Fun DIY Details

Itinerary

This blog post has the complete day-by-day GG weekend itinerary for a fall road trip. Or save it for later on Pinterest.

 
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Connecticut is the perfect places to go searching for Stars Hollow. Here’s everything my friend and I did on our girls weekend!
Gilmore Girls Weekend Itinerary (Fall Road Trip)
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📌 pin it for later!
📌PIN | The perfect Gilmore Girls road trip itinerary | Connecticut
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Places to Visit

Main highlights from the itinerary!

 
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A cute spot for breakfast and atmosphere—the coffee is not great (my friend and I pulled a Gilmore and only drank a few sips).
Theo's Downtown Diner
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Recommended for Lorelai-approved coffee (not really a Stars Hollow vibe but the coffee is excellent)
River & Rail Cafe
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THE Stars Hollow gazebo in the New Milford town green! Super cute place for photos.
New Milford Gazebo
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Where Amy Sherman-Palladino was staying when she got the idea to set the show in a cute CT town. Nice spot for lunch or just to visit.
Mayflower Inn & Spa (AKA Independence Inn)
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Adorable little bookshop in Washington Depot, CT. They even have a Gilmore Girls section.
Hickory Stick Book Shop
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Literally Doose's. 😍 The wallpaper!
Washington Food Market
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Adorable vibes and great spot to stop for a snack or coffee!
The Po Cafe
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Refueling spot because what's a Gilmore weekend without tons of coffee?
Marty's Cafe
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Not really a GG vibe but the food is awesome! Great spot for lunch.
The Pantry - Restaurant & Bakery
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Cute literary stop! This footbridge is very close to the parking lot and has Thoreau quotes all over it.
Henry David Thoreau Footbridge (Hidden Valley Preserve)
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Cute ice cream stop a la Taylor’s Olde Fashioned Soda Shoppe
Arethusa Farm Dairy
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Vote in the annual town scarecrow contest at Tapping Reeve Meadow—a very Stars Hollow-ish town event.
Town Scarecrow Contest
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Great spot for breakfast in Litchfield! Super cute small-town vibe and homey feel.
Love Heart's Bakery and Cafe
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Enjoy Rory's Yale years by wandering the beautiful campus in New Haven!
Yale Old Campus
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Fun DIY Details

If you want to add some extra touches or surprise your friends with little gifts, these are some ideas I used for our trip.

 
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Get a tote that's already printed with a cute design. Perfect for carrying around snacks and other items on your girls weekend!
Stars Hollow Tote Bag
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This is a super cute Stars Hollow graphic if you want to print your own products!
Graphic to Print Your Own Sweatshirt or Tote (Stars Hollow Autumn Festival)
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The exact graphic I used to get totes printed isn't available, but this one is pretty similar. I surprised my friend with these when she arrived!
Graphic to Print Your Own - Stars Hollow
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I loved this design and added some of these graphics to the printed itinerary I made!
Gilmore girls digital poster
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If you really want to go all out with your itinerary…😂 This is a paid font but it's THE one!
Sackers Solid Antique Roman Pro Regular
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Fun thing to add to a tote goodie bag for your favorite beverages at your inn!
Yale Koozies!
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