As we near the end of the school year, our sights are set on summer and the vacations it will bring. To make planning a little easier for you, we’re sharing a curated day trip guide to Winchester.
Pro tip: If you love taking the scenic route, we recommend heading straight out Winchester Road and taking Combs Ferry Road.
Stop No. 1 | Leisurely lunch at Beech Springs Farm Market, 4776 Old Boonesboro Rd. Like straight out of a movie, this roadside market features fresh produce, local jams and jellies, cheese plates, and pies. Sit for a spell in one of the rocking chairs or create your own fun with a game of cornhole.
Stop No. 2 | Wine tasting at Harkness Edwards Vineyards, 5199 Combs Ferry Rd. The Peach House is picture-perfect for a day with friends or a picnic with the family. Walk-in wine tastings are welcome or check the events page for classes such as paint + sips or cake-decorating.
Stop No. 3 | Treasure hunting at the downtown shops, Main Street Downtown Winchester is a thrift + antique lovers dream. Dirty South Pottery is a local favorite featuring handmade mugs, bowls, and full place settings.
Stop No. 4 | Catch a show at the Leeds Center for the Arts, 37 N. Main St. Plan your visit around one of the historic theater’s upcoming performances, or just pose for a picture under the bright lights.
Stop No. 5 | Brews with buddies at Abettor Brewing Company, 128 N. Highland St. Head down the brick road of Depot Street to close out the day with some local craft beer or cider.
Pro tip: Download the Tour Winchester app for even more fun places to eat, stay + play.