One Of The Best Little Towns To Visit In New England Is A Quaint Connecticut Gem With Cute Eateries And Wine

Named a "picture-perfect small town to visit in 2025" by Smithsonian Magazine, the town of Washington, Connecticut, has been charming people for years. In fact, the creator of the popular television show "Gilmore Girls" stayed at the Mayflower Inn and Spa in Washington (pictured above) while she was creating the show. She was so inspired by the town's vibe and architecture that she modeled the fictional town of Stars Hollow after it.

Heavy on New England charm with quaint shops, restaurants, and colonial buildings, most residents have roots in colonial history. For a small town (under 4,000 residents), Washington is surprisingly rich in culture, with a thriving food scene and artists of all types who come and go for creativity and inspiration. The independent, locally-owned Hickory Stick Bookshop has been an iconic spot for over 70 years, hosting many book launches and signings. In addition, the fairly rural town is surrounded by forests, lakes, and mountains, making it an ideal place to visit for a nice balance of nature and community.

Located in Connecticut's Litchfield County, Washington benefits from the picturesque backdrop of the Berkshire Mountains. If you're flying, Washington is one hour from Hartford-Brainard Airport; alternatively, it is also one hour from Tweed New Haven Airport. If you are driving, it's about an hour and a half drive from Manhattan or two hours from New York's oldest town, Albany. Within Washington, there are five villages: Washington Green, Washington Depot, New Preston, Marbledale, and Woodville. Minutes apart from each other, there are several great options for dining, drinking, and sleeping.

As mentioned, the Mayflower Inn and Spa is a stunning property to base yourself in Washington. An Auberge Resorts hotel, it is one of the largest and most modern properties available in Washington. Alternatively, there are several historic, colonial homes you can rent in their entirety. If money is no object, the Calhoun Estate is a gorgeous private home set on 15 acres. You can rent the entire property, but a summer-time rental runs around $35,000 per month.

An ode to our founding father, G.W. Tavern is a casual restaurant housed in a colonial home that dates back to 1850. In the summer, you can dine on the patio overlooking the Shepaug River, and in the winter, you can cozy up in front of the floor-to-ceiling fireplace. Local sourcing, sustainability, and community are the hallmarks of Community Table, another casual gathering spot and restaurant.

For me, there's nothing better than good wine paired with hand-crafted pizza, and The Owl has plenty of options for both. Spring Hill Vineyards is a sprawling winery that serves as a cool community gathering spot. Whether you go for a wine tasting or simply to spend an afternoon with friends, there is a large grassy area where kids can run around and play lawn games. In addition, they often host events with live music, dancing, and art.

Something educational and worth doing is the Wigwam Escape. An interesting escape room type concept created by The Institute for American Indian Studies, the experience takes you back to a Native American village in the year of 1518. While working together to solve a problem, the game was created to foster awareness and dialogue about the experiences of the Indigenous people who inhabited the Eastern Woodlands of Connecticut. The Gunn Memorial Library and Historical Museum features an immersive exhibit that dives into important local history, touching on themes surrounding Native Americans, colonists, the forming of the town, as well as slavery and abolition.

For nature lovers, an excellent place to see fall foliage, the 95-acre Lake Waramaug State Park is a dream for leaf peepers. The lake, whose name means "place of good fishing," is also a beautiful place to hike, camp, or enjoy water activities year-round. From Memorial Day through Labor Day, you can camp or rent a rustic cabin on the lake. If you're just going for the day, swing by The Smithy Market to pick up some yummy organic produce and picnic items on the way to the lake. Make sure to check out their art gallery in the loft of this reimagined blacksmith building.

Designated as a historical garden, Hollister House Garden is a town landmark that has been cared for lovingly by the same Washington resident and gardener for nearly 40 years. Open April through October, the English-inspired American garden is situated on the hillside of an 18th-century farmhouse. If you want to take advantage of your base in Washington and keep exploring Connecticut's unspoiled nature, just 30 minutes north of Washington, you can also venture out to explore the forest in Cornwall, dubbed the "greenest town in Connecticut."