Take a stroll down Thompson Street or hop off the Amtrak, and you might do a double-take. Neighbors and travelers alike are whispering the same thing: downtown Ashland feels just like Stars Hollow. From quirky shops to beloved eateries, this charming town exudes the warmth, humor, and community spirit that made Gilmore Girls’ fictional town so unforgettable.
Henry Clay Inn (114 N Railroad Ave)
Begin your Ashland adventure at the Henry Clay Inn (114 N Railroad Ave), where luxurious accommodations and friendly smiles make guests feel right at home. You might hear a playful request floating through the halls: “I’d like a cookie and a raise.” Much like Lorelai managing the Dragonfly Inn, the Henry Clay is a place where dreams meet hospitality—and every stay feels like a story unfolding.
Just a block away, Ash and Olive embrace the town’s sweet and savory side. With a menu built for comfort and delight, it’s easy to imagine a resident declaring, “It’s one of my four major food groups. Candy, popcorn, and pizza.” In Ashland, as in Stars Hollow, food isn’t just sustenance—it’s a reason to gather, laugh, and celebrate the small joys.
For those inspired to twirl, leap, or take a spontaneous jazz break, Ashland Dance Academy (110 Thompson St) is the town’s Miss Patty’s School of Ballet. Offering yoga, ballet, tap, and jazz, it’s where Ashland’s brightest stars shine, proving that “it’s moments like this that make life worth living,” just as the Gilmore Girls themselves would agree.
Ashland Meat Co (107 S Railroad Ave, Ashland, VA 23005)
Over at Ashland Meat Co, every plate is a declaration of dedication. Guests might echo the sentiment, “It’s not too much food. This is what we’ve been training for our whole lives. This is our destiny, this is our finest hour.” It’s a reminder that, whether you’re enjoying a perfectly grilled steak or a casual dinner with neighbors, Ashland honors the art of savoring life’s best moments.
Sweet tooth enthusiasts and pastry admirers will find their heaven at Bravo Bake Company (278 N Washington Hwy), where the rule is simple: “If eating cake is wrong, I don’t want to be right.” From buttery croissants to decadent cakes, every bite is a little indulgence reminiscent of a Stars Hollow afternoon filled with conversation, laughter, and perhaps a dash of mischief.
Book lovers, rejoice—Ashland Library (201 S Railroad Ave) offers the perfect Lorelai-and-Rory moment: “I live in two words. One is a world of books.” Step inside, and each shelf feels like its own paragraph in the story of Ashland, a place where imagination, knowledge, and community meet. Like the Stars Hollow library, it’s a quiet haven, full of discovery, inspiration, and endless charm.
Classic Coffee, Tea, and Books (112 Thompson St)
For a taste of the town’s musical and seasonal spirit, the Ashland Town Hall Pavilion (121 Thompson St) provides rocking chairs, live music, and porch displays that could rival any Stars Hollow gazebo. Local sponsor Foliage LLC by Richard Harding transforms this space into an autumnal wonderland, perfect for spontaneous sing-alongs or a heartfelt “You’re the best” moment with a friend.
Foodies will be delighted at Caboose Market and Cafe (108 S Railroad Ave), where farm-to-table fare could easily make a diner jealous. Move over, Luke; the sandwiches are only the beginning. And just around the corner, Classic Coffee, Tea, and Books (112 Thompson St) invites visitors to linger with a steaming cup and a good read—a cozy nook perfect for an “I just want coffee” moment, reminiscent of Stars Hollow Books’ charm.
Venture to Hickory Creek Antiques (427 England St), a treasure trove of over 40 vendors, and you might find yourself declaring, “I’ll take that!” From antiques to local art, it’s a place that captures the delightful unpredictability of Stars Hollow’s town shops. And for Italian cuisine lovers, IL Forno Bar & Grill (435 England St) offers flavors so authentic you might hear Lorelai sigh, “I’m not a pastry chef,” in admiration of the homemade pasta and sauces. Finally, at Sugar Fix Bakery (105 B England St), cookies are the main attraction, and one taste may leave you in a playful, “I’m in a cookie coma” bliss.
From morning coffee to evening strolls, Ashland proves that small-town charm never goes out of style. As neighbor and Downtown Ashland Association Executive Director “Coach” Antonio Miller says, “You haven’t really lived until you’ve been Gilmored in Ashland!” Whether you’re discovering hidden gems, sharing a laugh with neighbors, or simply soaking in the quaint streetscape, Ashland is a town where every visit writes its own story—one filled with warmth, whimsy, and that unmistakable Stars Hollow spirit.
For more information about visiting downtown Ashland, Virginia, go to https://www.ashlandvirginia.com/