Serenity & Scenery

Start your trip relaxing at Connecticut's largest and most awarded winery, Sharpe Hill Vineyard. Sip and sample homegrown flavors in their tasting room, including Ballet of Angels, the best-selling wine made in New England. And expect stunning views to set a scenic vibe. 

Next, head to Roseland Cottage Museum for some history, architecture, and gorgeous grounds. Explore the Gothic Revival style home and have a picnic on the lawn. 

That night, get inspired by a performance at Bradley Playhouse, a former vaudeville theater featuring assorted plays produced by a local performing arts company. And beforehand, enjoy an intimate dinner and dessert at Elizabeth’s Farmhouse. 

After, spend the night at the distinctive Inn at Woodstock Hill. This spot feels like an intimate hideaway — and offers views of the 19-acre property. No wonder it’s served as the backdrop for Hallmark movies! 

After breakfast at the inn the next morning, go hang out at Willimantic Brewing Company, a cool brew pub set in a former post office. Then explore Willimantic Downtown: a place where arts, theater, and business work together to create a center of culture, entertainment, and fun. Expect eye-popping events, museums, one-of-a-kind shops, and restaurants. 

Finally, stop in at the Nathan Hale Homestead, the family home of a Connecticut State Hero. Dig into history as you tour and explore the life of this Revolutionary War spy.