Black History Month Art Walk

Old Town Winchester 1 North Loudoun Street, Winchester, VA, United States

All February long, visit your favorite Old Town businesses to see brand new works of art from local Black artists up on display! We partnered with our friends at Arte Libre VA to commission new, original works in a celebration of Black culture in Winchester and to turn Old Town into a unique walking gallery ... Read more

Horse Drawn Rides in Old Town Winchester

Old Town Winchester 1 North Loudoun Street, Winchester, VA, United States

Join us in Old Town Winchester for complimentary horse-drawn rides from Shenandoah Carriage Company. Horse-drawn wagon rides will be complimentary and first-come first served and handled by the carriage company staff. Sit back, relax, and enjoy the lights and displays along the charming Loudoun Street Mall. Rides will begin on the south end of the ... Read more

Fiddles and Fifths

Old Town Winchester 1 North Loudoun Street, Winchester, VA, United States

Get ready for an unforgettable weekend as we send off summer with a tribute to the great Appalachian tradition of bluegrass music and the homegrown taste of Virginia bourbon! This returning event takes place in the heart of Old Town and brings a festival atmosphere that’s half world-class music mainstage, half backyard block party with ... Read more

Winchester Police Department Car Show

Old Town Winchester 1 North Loudoun Street, Winchester, VA, United States

Winchester Police Department will host a car show in Old Town Winchester (Piccadilly & Cameron Streets) in partnership with the Hoppers Auto Club, Inc. to benefit the Frederick County Winchester City Law Enforcement Foundation. Saturday, May 27th in Old Town Winchester from 11 a.m. to 5 p.m. Rain date Sunday, May 28th. Presented by Anthony's ... Read more

NYE Countdown and Apple Drop

Old Town Winchester 1 North Loudoun Street, Winchester, VA, United States

Join us as we ring in the New Year at at the intersection of Loudoun and Boscawen Streets! We will be dropping the traditional apple from First Night Winchester at midnight. Shops and restaurants in Old Town will be open extended hours. While things will look a bit different this year without First Night Winchester, ... Read more

Santa Bar Crawl

Old Town Winchester 1 North Loudoun Street, Winchester, VA, United States

Come out and join us for our Santa Bar Crawl in Downtown Winchester on December 10th from 1pm to 10pm. Entry fee is $10 dollars per person. There will be live music, amazing holiday drink and food specials with having a wristband to show at each location participating. We encourage all of you to dress ... Read more

Winchester Winter Market

Old Town Winchester 1 North Loudoun Street, Winchester, VA, United States

Join us December 10th for a Winchester Winter Market! Let's bring the community together by celebrating Christmas & supporting your local vendors and businesses. Old Town Spirit (Open Container) will be in affect during this event, so you're able to enjoy an alcoholic beverage while shopping! Bring the kids to the heated workshop for crafting, ... Read more

Windependent Weekend

Old Town Winchester 1 North Loudoun Street, Winchester, VA, United States

The holiday season is upon us, and there’s no better place to do your most important shopping than right in your own neighborhood. Whether you’re looking for unique gifts, unforgettable experiences, or top quality service, shopping local is guaranteed to give you just as much as you give back by spending your dollars close to ... Read more

Click here to view more upcoming events on our Winchester VA Events Calendar.