Feel like you’ve just stepped into Stars Hollow with a Gilmore Girls-inspired day in Woodstock, Illinois. With its cozy, character-filled charm, Woodstock brings to life the warmth and whimsy of the beloved town from the cult-classic show. Here’s your guide to a perfect fall day of “living like a Gilmore.”
Start your day, of course, with coffee. No Gilmore Girls day could begin any other way! Head over to Cornersquare Cafe for that classic, diner-style experience reminiscent of Luke’s, or swing by Ethereal for a coffee to sip while you stroll the Square.
Take in the sights and sounds of Stars Hollow (ahem, Woodstock). Wander through downtown, with its picturesque gazebo and tree-lined streets that seem straight out of a cozy fall scene from the show. Surrounded by the golden hues of autumn, Woodstock’s charm will make you feel like you’re in the heart of Stars Hollow.
Explore Woodstock’s version of Stars Hollow’s most iconic shops:
- Stars Hollow Books – Visit Read Between the Lynes, a cozy bookstore where you could imagine Rory spending hours.
- Doose’s Market – The Market by D&A has all the small-town grocery vibes.
- Taylor’s Old-Fashioned Soda Shoppe – RocketFizz is filled with nostalgic treats and charm.
- Kim’s Antiques – Find hidden treasures and quirky finds at Roscoe Antique Mall.
- Sophie’s Music – For all your musical needs, Jimmy’s Music offers a slice of Stars Hollow’s creative spirit.
Wrap up your day at “The Dragonfly Inn.” After a day packed with sightseeing and shopping, unwind with a stay at the Cherry Tree Inn—a perfect stand-in for Lorelai and Sookie’s famed inn. It’s cozy, welcoming, and the perfect place to rest after your Stars Hollow-inspired adventure.