Editors’ picks for exploring the town’s many charms.
Winchester has more than a few claims to fame. As one of the largest apple exporters in the country, it is the home of the annual Shenandoah Apple Blossom Festival, a 10-day extravaganza in late April that draws more than 250,000 visitors. But it is also a perfect stop for a day’s wander through charming shops, hip eateries, museums, gardens and more.
9:00 a.m. Bake It Up
On your way into town, stop at Bonnie Blue Southern Market and Bakery, which is housed in a converted 1920s era Esso station. Its neighborhood vibe will make you feel welcome as you fuel up on local favorites, including from-scratch biscuits, muffins and cakes, or go big with a plate of fried eggs draped over a juicy ribeye steak.
10:00 a.m. Walk About
Make your way over to Historic Old Town where you can get lost in the more than 100 shops, restaurants, art centers and museums lining its pedestrian mall. A handy app is available in the iTunes Store and on Google Play to help you navigate, learn about special events and find parking.
1:00 p.m. Find Some Coffee
Before you head out of Old Town, grab a matcha latte or espresso con panna at the Hideaway Café where all of the coffee is brewed with beans sourced from Red Rooster Coffee Roaster in Floyd. Stop at the register before you order to find out what’s on the secret R&D menu for the day.
2:00 p.m. Go Back In Time
Make your way over to the Museum of the Shenandoah Valley and explore the Glen Burnie Gardens—seven acres of formal gardens featuring boxwood, roses, perennials and vegetables as well as a water garden where golden trout swim in a spring-fed pond. Stop in at the museum store to buy seeds collected from the garden, including Sweet William, Black-Eyed Susans and cockscomb.
5:00 p.m. Tap Out
It’s just a quick five minutes back to Old Town for dinner at 50/50 Taphouse for that quintessential pairing—burgers and beer. Not sure which craft brew to order? Go with a flight of four pours from Virginia brewers, including Hardywood and Three Notch’d, or cider from Bold Rock (we love their new rosé). Then fill up on zesty fried pickle straws and the restaurant’s namesake burger topped with cheddar cheese, beer cheese sauce, and sautéed onions, mushrooms and bacon.
