(Shop Local) Daytripping in Winchester

Murals in Old Town Winchester paint the town a little brighter. Ashley Miller/Daily

WINCHESTER – For over 250 years the City of Winchester has been a commercial center, welcoming visitors since its inception in 1744 by Col. James Wood. It remains one of the oldest cities in the commonwealth west of the Blue Ridge Mountains. With over 28,000 residents, Winchester provides an oasis of charming architecture and authenticity, making the Downtown Walking Mall, and surrounding neighborhoods a unique living and shopping experience.

Jennifer Bell, downtown manager, said with over 35 restaurants and 60 shops within a four block radius, daytrippers flock to the city, as there are many things to see and do.   

“Winchester is a very warm and welcoming hospitable community,” Bell said. “Visitors come from all over to experience our urban amenities mixed with small-town charm. From historic museums to self-guided walking tours, good cuisine and shopping, we offer a very charming and unique experience for all.”

Visitors are encouraged to begin their day trip by stopping at the Old Town Winchester Welcome Center, open 8 a.m. to 5 p.m. Monday through Saturday on Boscawen Street where a wall of brochures with places to visit in the area hangs. A staff member is always on hand to answer questions and share suggestions.

There they will learn about the city’s self-guided walking tour of the community’s local history and architecture. Originally known as Opeckon and then Frederick Town, Winchester has experienced vast changes since its founding in 1744.

Mounted on the side of the Farmers and Merchants National Bank on South Loudoun Street, the clock is a timeless reminder of the unique characteristics of Old Town. Ashley Miller/Daily

First up on the self-guided tour is a Downtown Winchester must. Traveling from the Welcome Center down North Loudoun Street, visitors will stumble across the Shenandoah Valley Civil War Museum featuring over 3,000 Civil War artifacts. This popular landmark and tourist destination was once used as a hospital, barracks and prison by both sides during the Civil War.

Following the self-guided tour, visitors will travel down South Loudoun Street, where they will learn more about Winchester’s founding and history. Stops include The Holliday House, the James Dowdall Residence, Godfrey Miller Home, and First Presbyterian Church. A total of  30 stops encompass the walking tour.

While on the tour, visit various shops and boutiques along Loudoun Street. They include Wilkins ShoeCenter, Bell’s Men’s and Ladies’ Fine Clothing,  Make Next Interiors and Winchester Book Gallery.

“Some of our businesses date back 70 to 80 years, encompassing over 400 years of customer service,” Bell said. “Often family owned and operated, these businesses know everything about the products they sell and they take pride in their shared knowledge. Knowing their products and understanding customer wants and needs is what sets them apart from having customers shop online or going to chain stores.”

While searching for those one-of-a-kind gifts and souvenirs to take back home, enjoy one of 35 restaurants that serve up everything from contemporary American cuisine to authentic Thai, French pressed coffee and down-home cooking.

Bell's Fine Clothing, a long-standing Old Town staple, offers a wide selection of clothing for men and women. Ashley Miller/Daily

“Our walking mall lends to a relaxing, enjoyable shopping experience,” Bell said. “And I think that speaks to our town immensely.”

Bell said in her role as downtown manager and recent efforts have really spiked the interest in Downtown Winchester.

“Past perception of Winchester was that we use to be this sleepy little town that people would simply pass through on their way to another destination,” Bell said. “Now there’s a curiosity. A buzz because things are constantly changing. Now we’re the destination.”

Bell said locals and visitors alike are discovering that there’s a lot more to Winchester than meets the eye.

“Summer, for example, is a great time for day trips to Downtown Winchester,” Bell said. “We offer a Farmer’s Market on Thursday and Saturday, family movies sponsored by Parks and Recreation, classic movie nights, Friday Night Live and Shape Up Sunday’s. There’s a lot to draw from no matter your age.”

From pizza to authentic Mexican cuisine, Old Town serves up a wide assortment of food for all palates. Ashley Miller/Daily

Outside of the Downtown Walking Mall, Winchester and Frederick County offer visitors the opportunity to delight in other activities that include a family-friendly traditional drive-in movie theater, live music and entertainment throughout all four seasons, beer festivals and a  look at how the commonwealth has changed over the years.

“Between the town’s tasty selection of cuisine, to local artists and quaint shops, there are plenty of ways visitors can enjoy a day here in Winchester,” Bell said. “More than anything, I hope those that do travel through leave feeling welcomed. That they experience the warmth our city really has to offer and return home with some really great memories of their time spent in Winchester.”


Winchester and Frederick County residents shared their favorite places to go for food, fun and shopping:

Eat in Winchester

Refreshing beverages pair well with summertime favorites. Ashley Miller/Daily

Papermill Place, 2214 Papermill Road, Winchester

Traditional American comfort dishes draw in residents at this down-home establishment

Bonnie Blue,  334 W. Boscawen St., Winchester

A southern-inspired restaurant offering barbecue, fried oysters, and baked goods in a converted gas station

Firefly Cake and Bakery, 3035 Valley Ave. #101, Winchester

Completed in 1913, Handley Library, 100 W. Piccadilly St., in Winchester, stands as a landmark for city residents. Ashley Miller/Daily

Social enterprise, offering locally sourced gourmet food while providing vocational training and employment opportunities to individuals with disabilities

Play in Winchester  

Jim Barnett Park, 1001 E. Cork St., Winchester

Offering fitness trails, pools and playgrounds for kids of all ages

Museum of the Shenandoah Valley, 901 Amherst St., Winchester

Interprets art, history, and culture of the Shenandoah Valley

Oldtown Splash Pad, 121 S. Loudoun St., Winchester

This popular pad brings everyone out for summertime fun

Shop in Winchester 

Old Town Silversmiths, 152 N. Loudoun St., Winchester 

Created the ever popular Winchester bracelet and matching earring set

Creekside Gifts and Collectables, 3113 Valley Ave. #102, Winchester

Premier gift shop offering a wide selection of souvenirs and Virginia inspired gifts

Tin Top Art and Handmade, 130 N. Loudoun St., Winchester 

Dedicated to promoting independent artists and craft producers by bringing unique contemporary art and handmade goods to Winchester