Things to do in Winchester
Things to do in Winchester, newest first: events, festivals, parks and family days out, with dates, times and the organizer's own link.
Featured
Things to do in Winchester this month: October 2026
October in Winchester: pumpkin festivals Oct. 24, ghost tours on the mall Oct. 28-31, Haunted Nightmares, the Big Cheese Festival and the Last Sunday Market.
Plan your weekend
Halloween
Trick-or-treat hours in Winchester 2026
Halloween is Saturday, Oct. 31. Winchester had not set official trick-or-treat hours by Oct. 18; trunk-or-treat style events and ghost tours are listed here.
Trails
Parks and trails in Winchester
Winchester has more than 270 acres of parks, led by Jim Barnett Park, and the 6.06-mile Green Circle Trail. Parks open dawn to dusk. Parks office: 540-662-4946.
Halloween
Halloween events in Winchester 2026
Halloween 2026 near Winchester: Haunted Nightmares runs through Oct. 31, a flashlight corn maze Oct. 23, the Pumpkin Festival Oct. 24 and Old Town ghost tours.
Christmas
Holiday lights and Christmas events in Winchester 2026
Christmas 2026 in Winchester: Winter Village Dec. 5-6, Unsilent Night, museum holiday concerts, the Clearbrook light walk and where to see Santa.
New Year's Eve
New Year's Eve in Winchester 2026: Apple Drop and events
New Year's Eve 2026 in Winchester: the Old Town laser show and midnight Apple Drop, First Night at the MSV, Noon Year's Eve and free parking.
Valentine's Day
Valentine's Day in Winchester 2027: events, dinners, ideas
Valentine's Day 2027 in Winchester falls on a Sunday. Old Town's Chocolate Escape, Galentine's nights, a Valentine's brunch and date ideas, with last year's dates.
Mother's Day
Mother's Day in Winchester 2027: brunch, events and markets
Mother's Day 2027 in Winchester is May 9. Brunches, the George Washington Hotel luncheon, flower bars and plant sales, with last year's dates.
Free
Free things to do in Winchester: trails, history and festivals
Free things to do in Winchester: the Trails at the MSV, Kernstown Battlefield, the Green Circle, the mural trail and free festivals through the year.
Apple Blossom Festival
Shenandoah Apple Blossom Festival 2027: dates, parades, parking
The 100th Shenandoah Apple Blossom Festival runs April 23 to May 2, 2027, in Winchester. Parades, carnival, fireworks, closures, parking and bag rules.
Frederick County Fair
Frederick County Fair 2027: dates, tickets and grandstand shows
The Frederick County Fair runs July 26 to 31, 2027, at the Clear Brook fairgrounds north of Winchester. Admission, rodeo, derby and the week's lineup.
Patsy Cline
Patsy Cline Block Party in Winchester: date, music, parking
The free Patsy Cline Block Party is held each year on the Saturday of Labor Day weekend on South Kent Street. Times, trolley parking and 2027 news.
Apple Harvest Festival
Shenandoah Valley Apple Harvest Festival: dates, tickets, contests
The Rotary Club of Winchester's Apple Harvest Festival was Sept. 19-20, 2026, at the Clear Brook fairgrounds: $10 admission, pie contests, car show.