Story by Chelsea Rose Moore
Photos by Jacob Hurst

What city is home to an annual indie film festival and weekend food and beer tours? Here’s a hint: it also offers outdoor movie nights, a bustling nightlife, First Fridays, farmers markets, beer festivals, concerts and comedy nights, historical monuments, and Civil War battlefields. We’re talking about Old Town Winchester, which has become a hub for good food, artistic talent, and community.

Winchester has something for everyone. The Walking Mall is home to antique shops, galleries, escape rooms, knitting shops, home décor boutiques, clothing and shoe stores, and so much more!

Recent years have brought an explosion of creative energy to Winchester and its Walking Mall. Justin Kerns, the executive director of the Winchester-Frederick County Convention and Visitors Bureau, attributes this growth to an expansive renovation completed in 2012. The renovation added arches welcoming visitors to Old Town Winchester, a splash pad for kids, and public restrooms. Cleaning up the pedestrian mall brought a surge of new life to the city and attracted innovative new businesses and people.

Old Town Winchester.

“After the city said, ‘We are going to invest in the heart of our community,’ it significantly changed,” Kerns said, “It’s opened the door for a lot of creative small business owners. Before that, Old Town wasn’t really a place you wanted to go hang out. [Now] you have a lot of creative people moving in and that changes a vibe. We have a lot of women-owned small businesses, from restaurants to shops.”

There’s the popular Bright Box Theater, located in Old Town, which hosts multiple live shows and experiences each week, from comedy nights to local bands. It’s grown to become the heart of artistic talent in the city. Kerns pointed out that it’s woman-owned. So are local favorites, such as the Hideaway Café, Espresso Bar & Café, and Fresco Kitchen. And the list goes on. Locals flock to these places, because of the quality of food, the creative vibe, and the friendliness of its owners and staff.

Love country music? Winchester is Patsy Cline’s hometown. You can tour her home, walk the streets she walked, and even order burgers, fries, and milkshakes at one of her favorite restaurants (Snow White Grill, here’s looking at you!).

Can’t get enough of history? You’ll love Winchester’s National Historic Park, George Washington’s Office Museum, and Stonewall Jackson’s Headquarters Museum. You might also enjoy learning that Winchester’s streets have been graced by George Washington, Davy Crockett, and Stonewall Jackson. There’s history everywhere you look.

The Shenandoah Apple Blossom Festival, the king of Winchester’s annual events, finished up on May 5. Each year, thousands visit Winchester during its iconic celebration of spring. If it’s been awhile since you’ve explored Winchester, there’s no better time to visit. You might be surprised by what you find. Don’t know where to start? Let us help!

The Hideaway Café

A good starting point, this is a popular place amongst locals. If you’re looking to grab a quick bite, try their chicken salad sandwich, which is served on a croissant. Their chicken salad has a stellar reputation, some even referring to it as “legendary.” Locals buy it by the pint and take it home. The Hideaway Café also has a delicious stacked veggie sandwich and salad with strawberries, bacon, and goat cheese. Coming soon- coffee martinis. 141 S Loudoun St., Winchester

Hideaway Cafe.

Sexi-Mexi Burrito Bar

Walk into Sexi-Mexi Burrito Bar and you’ll be greeted by bright coral and lime green walls, vibrant murals, and a cool and eclectic vibe. You may have seen the Sexi-Mexi food truck at community events over the years. Owner Crissy Willis has run the food truck for eight years, taking it to music festivals, breweries, and special events, like the Lucketts Spring Market and Mother’s Day Garden Fair at Blandy Experimental Farm.

She wanted to replicate the positive vibes that came with the food truck and bring the same feeling to a brick and mortar shop. She opened her Winchester restaurant in October of 2017. “What always drew me to Winchester was the pedestrian-friendly nature of downtown,” Willis said, “The amount of time and energy the local government has put into marketing Winchester and beautifying it … [I knew] Winchester would be a demographic [that was] receptive to what Sexi-Mexi is trying to do.”

When she opened the restaurant, she wanted to keep things simple: serve as much local food as possible and design high-quality cocktails that were “crisp, clean, but flavorful.” Most importantly, she would keep her burrito-fusion that customers had come to love. Her creative burritos range from Mexican-style to Indian. She loves switching things out seasonally with rotating specials. Her cocktails are served in Mason jars with stainless steel straws, making it truly Instagram-worthy. 21 East Boscawen St., Winchester

Cuban Tostada at Sexi-Mexi.

Fellowship of the Sip

Fellowship of the Sip is one of Winchester’s hidden gems. As an organic tea house, restaurant, and tiny boutique, this family-owned place is calming and soul-soothing. The owners go the extra mile with all things, from growing their own sprouts to sourcing meats and cheeses from local farms. The white ginger peach tea is not to be missed. Neither is the gluten-free chocolate ginger cake, served with a dollop of whipped cream and a spoonful of jam. 33 S Loudoun St., Winchester

Fellowship of the Sip.

Moe’s Donut Shop

Light and airy, these donuts are dangerous for a couple reasons. First, they are unbelievably delicious. Secondly, they are so light you can eat a few without feeling them. Get here early in the day, before they close or sell out! 28 E Piccadilly St., Winchester

The German Table

Find schnitzel, bratwurst, sauerkraut, spätzle, pretzels with mustard, and German beer here. The German Table is modeled after a German “imbiss,” which is translated as “snack” or “a snack place.” In Germany, these are roadside food stands serving street food, designed for guests wanting a quick bite. “This is a very German-inspired place,” said owner Nathalie Miller. As a German herself, she grew up in Luxembourg and has always dreamed of opening a German restaurant. “I’m like a German Chipotle. It’s fast food.”

In keeping with its no-frills approach, The German Table doesn’t have a waitstaff; instead patrons order a la carte items from the counter. Just like at a German imbiss, food is served on paper plates. The German Table opened in October 2018, the night before Winchester’s Oktoberfest began. Miller loves watching German customers return again and again, finding a little taste of home in Winchester. 158 N Loudoun St., Winchester

The German table.

Espresso Bar & Café

This café is warm and moody. If you like your coffee on the sweeter side, order their oatmeal cookie latte. If you’re a tea lover, try their iced strawberry orange black breakfast tea. Head out back to their Secret Garden, containing a patio area with outdoor seating. There’s brick wall filled with vines that come to life in the spring, truly making the space feel like a hidden garden. 165 North Loudoun St., Winchester

Espresso Bar and Cafe Oatmeal Milk Latte and Strawberry Orange Black Breakfast Tea with Moe’s Donuts.

If you need to walk off your food, don’t miss the classic Kimberly’s Boutique, a Winchester mainstay, and The Polka Dot Pot, a bright and airy pottery-painting studio offering DIY classes. We love the Winchester Book Gallery, a 46-year old community bookstore. They host a plethora of events, book signings, and fun activities, like a blind date with a book. The Shenandoah Valley Discovery Museum will keep your kids engaged for hours. With multiple floors of learning activities, this will be a favorite stop for kids. If you’re in search of a nice dinner, head to Violino Restorante Italiano, a classic Italian restaurant serving amazing food.

We hope our little guide serves as a helpful starting point for your Winchester explorations! Other notable eateries that are not located on the Historic Walking Mall, but are absolutely worth a visit:

Hopscotch Coffee & Records

One-part hipster coffee shop, one-part record shop, with a hint of grunge and rock n’ roll, this place is a destination for artisan coffee lovers. 250 Millwood Ave., Winchester

Valerie Hill Vineyard & Winery

Come for the wine, stay for the history. This is a favorite for locals. 1687 Marlboro Road, Stephens City

Oak Stone Craft Pizza & Bar

Oak Stone is putting out the vibe, and we sure feel it. With an incredible seasonal cocktail menu and equally incredible wood-fired pizzas, this spot is definitely worth a visit – or two or five. 100 Valley Ave., Winchester

Crush Wine Bar

With an extensive wine menu and delicious small plates (think roasted bone marrow and shakshuka with quail eggs) and fun trivia games to play with your group, this is a worthwhile stop. 3031-103 Valley Ave., Winchester

Bonnie Blue Southern Market & Bakery

Texas-style barbeque, legendary biscuits, macaroni and cheese, and fried chicken. Need we say more? Don’t leave Winchester without stopping here. 334 W Boscawen St., Winchester

West Oaks Farm Market

West Oaks is a farm market for the whole family! Start with an afternoon of strawberry picking, then stock up on produce and locally made foods in the market, and end with soup, a sandwich, or a burger in the café. 4305 Middle Road, Winchester

This article first appeared in the May 2019 issue of Middleburg Life.