Explore Winchester & Litchfield Hills: Discover Your Perfect Day
Whether you’re looking to spark your creativity with a day of arts and inspiration, fill the day with family-friendly activities, or treat yourself to shopping, restaurants, and local delights. Winchester, Winsted (part of the town of Winchester), and Litchfield Hills have it all.
DAY TRIPS | LOCAL FAVORITES | BUSINESS CIRCLE MEMBERSHIP
DAY TRIP: A Day of Art & Creativity
Art, Music, and Local Eats in a Vibrant New England Town
Kick off your day at the American Mural Project (AMP) to be wowed by the monumental indoor mural that celebrates the spirit of American workers. Then stroll to Whiting Mills to browse studios and workshops filled with artisan crafts and local artwork. Before lunch, stop at indie bookstore The Curious Cat Bookshop for a carefully chosen selection of books and gifts. Hungry? Try lunch at Railway Cafe or Mama Pho for Vietnamese delights. Afterward, head to The American Museum of Tort Law to discover quirky, thought-provoking exhibits on the impact of consumer protection law on our lives. Stop for a snack at Papa Boba Tea Bar & Dessert, then head to Still River Studio and Art Gallery, a working studio and retail art gallery created by a group of northwest Connecticut artists. F&G Richards Jewelers is right next door. And don’t miss Home & Cake’s curated selection of kitchen and home decor. Wind down the day with a delicious dinner at Noujaim’s Mediterranean Bistro, seafood and American classics at The Tributary or Royal Coachman Tavern’s burgers and pizza.
Cap off your evening with live music at 2nd Home Lounge (local wines, distilled spirits, and small plates) or Little Red Barn Brewers (craft beers and comfort eats). If you’re enchanted by Winsted’s creative energy, stay overnight nearby at the historic Manor House Inn or Old Riverton Inn.
DAY TRIP: A Family Fun Day in Winsted
From Hands-On Art to Bowling and Go Karts, Winsted Offers Fun for the Whole Family!
Start the day with a family-friendly adventure at the American Mural Project where kids can explore the mural exhibit through a scavenger hunt, I-Spy challenges, and art activities just for them. Afterward, enjoy a pick-me-up at Papa Boba Tea Bar & Dessert, then explore Mad River Music's collection of instruments before heading to The Curious Cat Bookshop to browse the books.
Fuel up with homemade soups and sandwiches at Railway Cafe, noodles at Mama Pho, or BBQ handhelds and flatbreads at Little Red Barn before diving into a game of mini-golf, bumper cars, or go-karts at R&B Sports—or test your skills with a game of duckpin bowling at Laurel Lanes. Is being pampered your idea of a good way to bond? Book a dual manicure or pedicure at Wonderland Nail Studio. And if you’re looking for something more heady to spark discussions, visit The American Museum of Tort Law. Don’t miss a family photo op in front of the Corvair parked inside!
After you’ve worked up an appetite, enjoy family favorites at Royal Coachman Tavern or The Tributary, the fun ambiance and variety of tastes at 2nd Home Lounge, or authentic fare at Noujaim’s Mediterranean Bistro. With easygoing entertainment and activities around every corner, you’re sure to create happy family memories.
DAY TRIP: Shop, Stroll, and Savor in Winsted
Unique Shops and Dining Delights in a Charming Town Setting
Begin your day with inspiration at the American Mural Project’s indoor art exhibit and take home a hand-painted shirt or hoodie. Stop for a refreshment at Papa Boba Tea Bar and Dessert, then meander the crafts and curiosities at Whiting Mills. For lunch, grab a bite at Railway Cafe, Mama Pho, or Little Red Barn Brewers. Then, spend the afternoon exploring downtown’s unique offerings—lose yourself in books at The Curious Cat Bookshop, find charming home décor at Home & Cake, and treat yourself to a fresh manicure at Wonderland Nails or a new treasure from F&G Richards Jewelers. For dinner, savor the flavors of Noujaim’s Mediterranean, seafood at The Tributary, or a laid-back meal at Royal Coachman Tavern. Ready to keep the evening going? Enjoy live music, local wines, craft distilled spirits, and farm-to-table delicacies at 2nd Home Lounge before retreating to a cozy night’s stay at Manor House Inn or Old Riverton Inn & Royal Coachman Tavern—for the perfect weekend escape.