Plan an unbeatable itinerary by starting early with coffee and a croissant at Jackson & Co., then explore Raindrops in Virginia for handcrafted treasures and Weaver Street Shops for Native American jewelry and vintage quilts. Stop by Verdent, Monica Garrett’s interior design storefront for epic home inspiration. Art lovers will treasure Annie Gould Art Gallery and owner Annie Gould’s keen eye for exceptional art, while gift-hunters can’t miss Laurie Holladay Shop, unofficially the best gift shop in the world. Fashionistas will love what’s in store at Posh.
Hungry? For lunch, try Well-Hung Vineyards for their signature flatbreads and wine flights, or relax on the front porch of Barbecue Exchange, with its delectable array of sandwiches and Southern sides. For dinner, indulge in French cuisine at Près des Prés. Make time to pamper yourself with a facial or massage at Sanctuary Spa & Wellness or drop in for a class at Atha Yoga. Fancy a longer stay? Book an overnight in Main Street’s one-bedroom Airbnb. It’s über convenient and provides easy access to historical sites like Montpelier and Monticello. And for wine lovers, Barboursville, Southwest Mountain, and Horton Vineyards are also nearby.
Gordonsville Main Street. Photos courtesy of Gordonsville
This article originally appeared in the Best of Virginia 2025 issue.
