Spend some time in Old Town Winchester, and it will quickly become a favorite day-trip destination. Although it’s thoroughly modern today, this town in the Shenandoah Valley played a pivotal role in American history, dating back to when Pennsylvania Quakers first settled on Shawnee camping grounds more than 290 years ago. Two decades later, 16-year-old George Washington surveyed the region for Lord Thomas Fairfax, and the future president held his first public office by representing Winchester in Virginia’s House of Burgesses. Efforts to control this strategic location led to six Civil War battles, and the town changed sides 70 times. (You can learn more about Winchester’s history on the Express Trolley sightseeing tour.) We’ve focused our visit around the 45-block National Historic District, specifically Old Town’s pedestrian mall on Loudoun Street, where you’ll find a mix of vintage eateries, stylish watering holes, and artisan boutiques selling an array of Virginia-made products. Every spring, the town hosts the Shenandoah Valley Apple Blossom Festival to celebrate the town’s bountiful orchards bursting with pink and white flowers. With so many stellar attractions, we think your visit to Winchester will be the first of many.
1. Grab a whoopie pie and espresso at the Hideaway Café, where the vibe is progressive and the theme global. Along with serving coffee, sandwiches, and desserts, owners Victoria Kidd and Greg Armstrong sell supplies to make your best cup at home, whether that’s matcha or French roast. 141 S. Loudoun St., Winchester
2. While waiting for your fried green tomatoes to arrive at Water Street Kitchen, look over the shelves stocked with craft beer and wine. These beverages are for sale, or you can open them at your table for a $7 corkage fee. Water Street Kitchen and Village Square Restaurant, across the street, are owned by Winchester Mayor John David Smith Jr. and his partner Joerg Eichmann. 2 S. Loudoun St., Winchester; 103 N. Loudoun St., Winchester
3. Sexi-Mexi Burrito Bar is one of Winchester’s most popular eateries, and for good reason. Whether its crafty cocktails or a hefty burrito you seek, chef Cristina Willis’s global flavors will tantalize your taste buds. We’re partial to the Crazy Cuban and the Smokin’ Bloody Maria. 21 E. Boscawen St., Winchester
4. Grab a booth at The Wine Room at Taylor Pavilion, where you can sample wines by the glass until you find your favorite (designated driver required). In fine weather, this chic urban bar swings open its garage-style doors, offering views of Winchester’s Taylor Pavilion, an outdoor venue that hosts live music and movies. 120 N. Indian Aly., Winchester
5. History buffs should stop in the Shenandoah Valley Civil War Museum, in the center of Winchester’s pedestrian mall. The Greek Revival courthouse walls are sketched with graffiti left behind by Northern and Southern soldiers who were imprisoned, received medical treatment, or were housed in barracks during the Civil War. There are 3,000 artifacts on display upstairs. 20 N. Loudoun St., Winchester
6. Whether you’re craving homemade fudge or keto-friendly baked goods or are in search of new kitchen gadgets, Nibblins has you covered. The culinary boutique carries top brands like Le Creuset and Wüsthof, as well as Tervis tumblers and canning supplies by Kilner. 27 N. Loudoun St., Winchester
7. Celebrating its 91st anniversary this year, the family-owned Bell’s Fine Clothing sells hard-to-find, upmarket garments. Look for designers like Boglioli, known for men’s soft coats and ladies’ dresses; shaving products by the oldest barbershop in the world, Truefitt & Hill; and hand-sewn Italian shoes by To Boot. 122 N. Loudoun St., Winchester
8. Tin Top Art and Handmade is a small gallery that elevates artists who have a finger on the pulse of what’s happening in the world. Among the whimsical finds are hand-sewn baby burp cloths, Meadowland fruit syrups, DIY embroidery kits, and circuit-board tie bars. 130 N. Loudoun St., Winchester
9. At Handworks Gallery, we’re fans of the travel jewelry cases, frying pan necklaces, and colorful ceramics by local potter Neena Jhaveri. 150 N. Loudoun St., Winchester
10. Perch on a barstool at Old Town Snow White Grill and check out the black-and-white photos. Country crooner Patsy Cline grew up in Winchester and was a regular, ordering the diner’s famous mini-burgers and strawberry ice cream. 159 N. Loudoun St., Winchester
Winchester’s Shenandoah Valley Apple Blossom Festival celebrates its 95th year this year from April 22 to May 1 with 10 days of fan-favorite events, including the signature Bloomin’ Wine Fest, Grand Feature Parade, carnival, apple pie baking contest, Bloomin’ Sunday car show, and a ’90s dance party.