Things to Do in Winchester and the Area

Please also check the following websites for further information:

Old Town:

Winchester is a lovely small city with an historic center. The Old Town streets are lined with brick sidewalks, beautiful homes, historic buildings, and different styles of architecture, so just strolling around is enjoyable in itself. In quaint Old Town you’ll find:
Many specialty shops, small galleries, a variety of restaurants (both casual and upscale), outdoor cafes, and nightlife.


Winchester has an excellent variety of local restaurants to fit all tastes and budgets, and many of our very best are within walking of the inn. Your hosts are very familiar with the local restaurants and can make recommendations to best suit your needs

Theatre and concerts:

• Winchester Little Theatre
Shenandoah University concerts and Summer Theatre shows
Wayside Theatre in nearby Middletown
Bright Box Theatre

Historic Interest and Museums in Winchester and nearby:

•  Glen Burnie historic home and garden tours (home of Winchester’s Founder James Wood)
Abram’s Delight museum, George Washington’s Office and other historic buildings see
Civil war battlefield sites and reenactments
Belle Grove Plantation
Historic Long Branch
Patsy Cline Museum, within walking of the Inn.
Museum of the Shenandoah Valley

Annual Events :

Apple Blossom Festival each May
Historic garden tours in April
(Nearby) Mountain Heritage Arts and Crafts Festival(25 minutes away) every June and September
Apple Harvest Festival each September
First Night each New Year’s Eve


Old Town has unique shops and small galleries selling gifts, pottery, books, original art and framed prints, furniture, antiques, gourmet items, wine and specialty beer, home décor, fine linens, candles, jewelry, clothing and more. Winchester also has an upscale shopping complex called Creekside Village, and numerous chain stores as well.


Winchester has several antique shops that carry a wide range of quality antiques, used furniture, and flea market items. In addition this is good base for area antiquing. Just 20 miles south, Strasburg is the antique capital of the area, with a large emporium and several individual shops.

Outdoor and sports in Winchester and the area:

•5 public golf courses, miniature golf a few miles north of town. Rock Harbor is the closest to the Inn.
• Hiking nearby (15 minutes to Sky Meadows State Park, 30 minutes to the start of the Skyline Drive and Blue Ridge hiking)
• Hot Air Balloon rides with Blue Ridge Hot Air Balloons
• Fishing in the Shenandoah River


Winchester is a good base to visit many wineries and to take scenic drives. A map of Virginia wineries is available, or go to to plan your trip.