Where You Lead, I Will Follow: Gilmore Girls Inspired Getaways

If you’re a fan of the hit TV show Gilmore Girls, you’re in for a real treat. There’s something about fall that just makes me want to re-watch Gilmore Girls for the hundredth time. And every time I do, I can’t help but admire the gorgeous locations in which the show was filmed in. Everything looks so warm, charming, and inviting. And even though Stars Hollow is a fictional place, there are still stunning real towns that resemble it. That’s why we decided to share with you some real-life destinations scattered across the United States that will make you feel like a resident of Lorelai and Rory Gilmore’s captivating universe. Grab your coffee and lip gloss, and let’s get started with our Gilmore Girls inspired getaway.

Luke’s Diner: Coffee and Conversation in Connecticut

Our adventure commences in Washington Depot, Connecticut. While it may not be the exact filming location, this idyllic town served as the inspiration for the show’s creator, Amy Sherman-Palladino. Your first mission? Seek out a local diner, order a cup of coffee, and channel your inner Lorelai and Rory. While you may not discover Luke’s Diner, the profound warmth and timeless charm of this small town will seamlessly transport you into their world.

Visit the Gilmore Mansion: Say Hello to Emily and Richard

To experience a taste of Gilmore opulence, venture to the Mayflower Grace Inn, also nestled in Washington, Connecticut. While an overnight stay within the Gilmore Mansion remains an unfulfilled fantasy, a visit to this luxurious inn will effortlessly transport you into the refined world of Emily and Richard Gilmore. Treat yourself to a rejuvenating spa day or embark on a leisurely stroll through the exquisitely landscaped gardens – activities reminiscent of the Gilmores’ refined tastes.

Stars Hollow, Anyone?


Although Stars Hollow itself remains a creation of imagination, Washington Depot effortlessly steps into the role. Traverse its picturesque streets, gracefully adorned with historic buildings and charming boutique shops. With every step, you’ll feel as though you’ve transcended into the iconic opening credits of the show.

Explore the Quirky Town of New Haven

A brief jaunt from Washington Depot leads you to New Haven, Connecticut. While Stars Hollow’s Yale University may not be found here, the same quirky charm and intellectual aura prevail. Immerse yourself in the rich campus culture by embarking on a guided tour or perusing the renowned Yale University Art Gallery. Afterwards, savor a meal at one of the town’s cozy cafes, allowing yourself to become enveloped in the intellectual ambiance cherished by Rory Gilmore herself.

The Dragonfly Inn: A Dreamy Stay in New England

Continue your journey to Lenox, Massachusetts, where the enchanting Wheatleigh Hotel awaits. This elegant establishment, which served as the inspiration for the Dragonfly Inn – the heart of Stars Hollow, exudes timeless charm with its classic architecture and immaculate gardens. Visualize yourself sipping coffee on the porch, eagerly anticipating your next Gilmore-worthy escapade.

Chilton: Channel Your Inner Rory

Rory Gilmore’s academic pursuits led her to Chilton, an esteemed preparatory school. In Lenox, you can explore the Cranwell Resort, reminiscent of Chilton’s grandeur. Even if you’re not pursuing an education, you can relish in the resort’s opulence, indulging in spa treatments, rounds of golf, and impeccable fine dining. This is your chance to immerse yourself in the same sophistication that played a pivotal role in shaping Rory’s character.

Kanita Bajrami

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