This May, when our youngest graduates from The Gunnery, our rhythm of monthly trips to Washington, Connecticut will change. For the last five years, this corner of storied Litchfield County has been woven into our family’s life, and we can’t think of a more beautiful place to recommend for a weekend visit…or longer. Washington has every ounce of charm you might expect of a colonial New England town. White clapboard homes circling the town green; stone walls so beautifully preserved, it is impossible to distinguish where the historic ends and the new begins; an endlessly chic and equally charming shopping district; meticulously maintained hiking trails; ancient trees that are resplendent in fall; and a private boarding school founded in 1850 that blends seamlessly into the community. At the center stands the stately First Congregational Church, founded in 1801, its quietly commanding Puritan presence anchoring it all.
Washington is a residential community, divided into five distinct villages and areas spanning 38 square miles. Its historic heart is the village of Washington Green, home to The Frederick Gunn School (which we will forever call by its original name, The Gunnery), the library, two museums, several churches, the welcoming and delicious Po Café, and the stylishly luxurious Mayflower Inn and Spa (most recently updated by renowned interior designer Celerie Kemble). As fans of Gilmore Girls may know, it is said that the show’s creator, Amy Sherman-Palladino—inspired by the community’s charm and close-knit feel—based the fictional town of Stars Hollow on Washington while a guest at the inn.
Just a mile down the hill sits the village of Washington Depot, a former stop along the Shepaug Railroad and now the community’s modern hub. Here you’ll find the grocery and liquor stores, the town hall, a beautifully curated interiors resource—George, several restaurants, galleries, a small service station, and a handful of beloved shops, including The Hickory Stick Bookshop, J. McLaughlin, and the impressively stocked local hardware, Washington Supply Company. The Depot is also surrounded by miles of well-maintained hiking trails, thanks to the Steep Rock Nature Preserve‘s donors and volunteers, that offer varied terrain, including an incredibly scenic overlook at Steep Rock Summit.
To the north and south along Route 202 lie the villages of Marbledale and Woodville, the bookends of Washington. You’ll find a small cluster of businesses in Marbledale, including a lovely yarn store and the reliably cozy White Horse Tavern—always busy and, seemingly, always open. Woodville is home to the widely respected Washington Montessori School, which neighbors the well-regarded dinner spot, Community Table. If you are lucky enough to secure a reservation at this beloved and award-winning restaurant, go. Chef Bolivar Hilario was most recently named a 2026 James Beard Award Semifinalist for Best Chef: Northeast—a fitting accolade. I enjoyed one of the most memorable birthday dinners of my life here and have promised myself another visit before graduation!
Rounding out the five is the village of New Preston, an unexpected shopping haven tucked into a wooded ravine. Former 18th and 19th-century buildings perch in storybook fashion above a stream whose waterfalls once powered active mills. The little village is now home to an astonishing collection of high-end shops offering clothing, home goods, and more. Don’t miss Plain Goods, DK. Schulman, Pergola, J. Seitz & Co., and the rest of this tiny but mighty retail district. And for breakfast? The Smithy Cafe at 9 Main makes remarkably good breakfast sandwiches, pastries, and coffee; our entire family is devoted. If you still need to stretch your legs after it all, the trails within the Macricostas Preserve won’t disappoint.
Beyond hiking, the area offers an impressive array of outdoor pursuits. In nearby Millbrook, NY, Orvis Sandanona Shooting Grounds offers sporting clays, upland and waterfowl hunting, and world-class wingshooting instruction. Fly Fishing Connecticut provides guided outings on the Housatonic and Shepaug Rivers (among others) as well as instruction for beginners and experienced anglers alike. In the winter, Mohawk Mountain is the area’s beloved local ski hill with a welcoming, family-friendly vibe. And if you enjoy a beautiful, Nordic ski day like us, Maple Corner Farm—a bit of a drive north into the southern Berkshires—boasts over 20 km of groomed trails, rentals, and a small on-site restaurant.
But before you leave town, take time to simply wander the backroads to gather design and landscape inspiration from the impressively beautiful homes, country estates, and natural vistas. And if you decide you never want to leave (who could blame you?), William Pitt Sotheby’s has an office located directly in Washington Depot. You’ve been warned: Be prepared to fall in love.
