Winchester: Virginia’s Valley Gateway

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Winchester, Virginia’s northern gateway to the Shenandoah Valley, is a vibrant combination of contemporary city life and preservation of an historic past.

“As the Winchester area develops into a significant leisure tourism hub in the Northern Shenandoah Valley, we are increasingly drawn to our deep and complex past to uncover fascinating stories of how we became who we are today,” said Justin Kerns, Director of the Winchester-Frederick County Tourism Office. “We are excited to share those discoveries with our growing number of visitors from around the world.”

New visitors to Winchester often head straight for picturesque Old Town, which combines shopping, dining, arts and entertainment, nightlife and daytime strolls. The Farmer’s Market, operating on Saturdays from May to September, is bursting with local fruit, vegetables, beef, eggs, cheese, jam, honey, and bread.

History lovers can explore Stonewall Jackson’s headquarters on North Braddock St., or visit other diverse sites such as Cedar Creek & Belle Grove National Historical Park, the Civil War Orientation Center, or the Patsy Cline Historic House.

This year, however, there is one attraction that may dwarf all the others—the 90th Shenandoah Apple Blossom Festival, April 28-May 7.

While perhaps a bit less raucous (and much more inviting to families), the Apple Blossom Festival is as synonymous with Winchester as Mardi Gras is with New Orleans. Over 90 years, it has earned a variety of awards from Fordor’s Travel, the American Bus Association, USA Today and many other outlets.

Festival activities, far too numerous to list here, include wine fests and tastings, mountains of food, parades, live music, talent shows, carnival rides, dinners, luncheons, receptions, pageants and coronations, pie contests, kids races, dances and balls, arts and crafts. Four new events this year include: the Bloomtown Derby—A Wine and Food Experience, New Dance Party–A Night in Havana, a Ladies Commonwealth Brunch, and the first UTA-sanctioned Tennis Tournament.

There is more, but you get the idea.

While the Apple Blossom Festival lasts 10 days, other forms of fun can be had all year. Some highlights:

Shenandoah Summer Music TheatreBe Entertained

Shenandoah Summer Music Theater presents several musicals each season. The lineup for 2017 is: Oklahoma! (June 22-July 2), Beauty and the Beast (July 6-16), and Hairspray (July 20-30). Founded in 1984, the theater was created to give Shenandoah Conservatory theater students an opportunity to gain professional experience before embarking on their own careers in the field.


One Block West—Just a block from Winchester’s “Walking Mall” in Old town, One Block West is committed to using locally grown ingredients and has about 80 wines to choose from that will complement their upscale, seasonal cuisine.

Violino Ristorante—Family owned and in operation since 1996, Violino Ristorante serves homemade Italian dishes that have earned Peoples Choice “Best Food” awards. The husband and wife owners are native Italians.

Pick your own fruit and vegetables at Marker-Miller Orchards Farm Market and Bakery, opening June 1st in 2017. About 350 beautiful acres of apple and peach orchards, along with picnic tables, live music, bakery sweets, cider, jams, jellies, and wagon rides for the kids, make this more of a full day trip than a casual visit.

Go Back in Time

Cedar Creek and Belle Grove National Historical Park—Civil War history runs deep throughout the Shenandoah Valley, and this historical park was established to preserve the site of an 1864 battle. A Visitor Center, guided and self-guided tours and ranger programs enhance the experience. According to Kerns, “New Civil War battlefield developments and expansions are underway as well, such as the Kernstown Battlefield, expanding in 2017, and the transformation of the Old Court House Civil War Museum into the Shenandoah Valley Civil War Museum.”

Just outside Winchester in Stephens City is the Newtown History Center, one of many small museums in the Valley that do an exceptional job of preserving local history. Here, interpretive displays showcase the town’s wagon-making history and cultural heritage of the region’s early settlers. Operated by the Stone House Foundation, the museum’s hour vary seasonally; June through August are the most popular months to visit.


Best Western Lee-Jackson Inn and Conference Center—This trusted-name hotel is ideally situated for tourists or business travelers. Near I-81, the Winchester Medical Center, Apple Blossom Mall, and Shenandoah University. Newly remodeled rooms and group rates for AAA, AARP, CAA and others.

George Washington A Wyndham Grand Hotel  With a health spa, indoor pool designed like a Roman bathhouse, a fitness center, a 24-hour business center, two dining options, suites with gas fireplaces, and 6300 square feet of meeting space, the Wyndham fits the bill for any type of traveler.

For more information about Winchester and Frederick County, visit:

Banner photo—Shenandoah Apple Blossom Festival courtesy Christopher Hunter Photography/Virginia Tourism Corporation




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