What's On in Winchester
Events, markets, games, library and parks programs in and around Winchester, with times, prices and the organizer's own link.
Featured
Winchester Fourth of July fireworks 2027: Red, White and Boom
Winchester's Red, White and Boom fireworks were July 3, 2026, at 9:20 p.m. in Jim Barnett Park. Viewing, parking and closures; 2027 date not yet set.
Coming up
The full month- Now through Nov. 28 The Wickhams: Christmas at Pemberley
- Nov. 14 to 15 Virginia Gourd Show and Sale
- Sat. Nov. 21 Kris Kringle Market at Belle Grove
- Sat. Nov. 21 The YDC's 2026 Festival of Trees
- Thu. Nov. 26 Thanksgiving Day 5K, Kids' Fun Runs and Tot Trot
- Thu. Nov. 26 Thanksgiving Day 5K
- Sat. Nov. 28 Holiday Craft Show at West Oaks Farm Market
- Sun. Nov. 29 The Last Sunday Market
- Sun. Nov. 29 Museum Store Sunday at the MSV
- Mon. Nov. 30 Winchester Holiday Parade and Tree Lighting
- Dec. 4 to 6 Winchester Old Town Winter Village
- Sat. Dec. 5 Holiday Workshop: Door Swags
More in What's On
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.
Christmas
Winchester Christmas parade and tree lighting 2026
Winchester's Holiday Parade is 7 p.m. Monday, Nov. 30, 2026, followed by the tree lighting on the walking mall. Entry deadline for floats: noon Nov. 2.
High school football
Friday night football in Winchester 2026: Handley schedule
John Handley's last two regular-season games are Saturday, Oct. 24, vs. Sherando and Saturday, Oct. 31, vs. James Wood, both at 1 p.m. Scores and how to watch.
Fall festivals
Fall festivals and pumpkin patches near Winchester 2026
Pumpkin patches and fall festivals near Winchester: Marker-Miller's Pumpkin Festival Oct. 24, Shawnee Springs picking, Hill High Farm, corn mazes and hayrides.
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.
Thanksgiving
Thanksgiving in Winchester 2026: 5K, events, trash changes
Thanksgiving 2026 in Winchester: the Thanksgiving Day 5K at Sherando Park, the trash and recycling shift to Friday, the Holiday Parade on Nov. 30.
Black Friday
Black Friday and holiday shopping in Winchester 2026
Black Friday 2026 in Winchester: Apple Blossom Mall hours, Old Town's small shops, free meter parking Nov. 27, and Winter Village on Dec. 5-6.
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.
Spring break
Spring break in Winchester 2027: dates, camps, things to do
Winchester Public Schools' spring break is March 29 to April 2, 2027. The city's spring break camp, library and museum ideas, pools and what is open.
Easter
Easter in Winchester 2027: egg hunts, brunch and services
Easter 2027 in Winchester is March 28. The city's Flashlight Egg Hunt at Jim Barnett Park, farm and brewery egg hunts and church services, with 2026 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.
Memorial Day
Memorial Day in Winchester 2027: ceremonies, trash, pools
Memorial Day 2027 in Winchester is May 31. The Healing Field of Honor, Winchester National Cemetery, trash pickup delays, free meters and the pool opening.
Summer
Summer in Winchester 2027: camps, pools and splash pads
Summer 2027 in Winchester: the city day camp, the Jim Barnett Park outdoor pool from Memorial Day weekend, the splash pad's return and summer theater.
Father's Day
Father's Day in Winchester 2027: events, car shows, brunch
Father's Day 2027 in Winchester is June 20, the day after Juneteenth. Car shows, weekend brunch, breweries, ballgames and last year's events.
Labor Day
Labor Day in Winchester 2027: events, closings, trash pickup
Labor Day 2027 in Winchester is Sept. 6. The Patsy Cline Block Party, the outdoor pool's last weekend, trash running a day late and free meters.
Brunch
Brunch in Winchester: 12 places with weekend brunch hours
Weekend brunch in Winchester at 12 restaurants, diners and bakeries, with days, hours and addresses from each one's own site, mostly in Old Town.
Dogs
Dog-friendly Winchester: parks, patios, trails and leash rules
Dog-friendly Winchester: the free dog park at Jim Barnett Park, leash rules in city parks, trails that welcome leashed dogs and patios that allow them.
Kids
Kids' activities in Winchester: playgrounds, story times, rainy days
Things to do with kids in Winchester: Jim Barnett Park playgrounds, free library story times, the Discovery Museum, indoor pools and rainy-day picks.
Trails
Winchester walking and biking trails: Green Circle, MSV and more
Winchester's walking and biking trails: the 6.06-mile Green Circle loop section by section, the free Trails at the MSV, Abrams Creek and parking.
Old Town Winchester
Old Town Winchester: a guide to the Loudoun Street Mall
A guide to Old Town Winchester and the car-free Loudoun Street Mall: museums, food, parking, the DORA sip-and-stroll zone, murals and walking tours.
Live music
Live music and nightlife in Winchester: venues, pubs, late bars
Where to hear live music and go out in Winchester: Bright Box Theater, Blue Fox Billiards, Old Town pubs and taprooms, wine bars and late-night spots.
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.
Date night
Date night in Winchester: dinner, wine bars, theaters, late spots
Date night in Winchester: Old Town dinner spots, wine bars that take reservations, a rooftop bar, live shows, a drive-in and late-night options.
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.
Restaurants
Where to eat in Winchester: lists by category
Every Winchester eating list in one place: wings, pizza, Mexican, sushi and Asian, burgers, breakfast, bakeries, desserts, patios, brunch and date night.
Wings
Where to get wings in Winchester: Old Town and Pleasant Valley Road
11 places to get wings inside Winchester city limits, from the Loudoun Street Mall and Cork Street to Pleasant Valley Road and Valley Avenue.
Pizza
Where to get pizza in Winchester: Old Town and Pleasant Valley Road
11 pizza places inside Winchester city limits, from wood-fired and 28-inch pies in Old Town to delivery chains on Valley Avenue and Pleasant Valley Road.
Mexican food
Mexican and Tex-Mex restaurants in Winchester
11 Mexican and Tex-Mex restaurants inside Winchester city limits, in Old Town, on North Loudoun Street and along Pleasant Valley Road.
Patios
Patios and outdoor dining in Winchester: Old Town and Valley Avenue
8 Winchester restaurants whose own sites list a patio or outdoor seating: five in Old Town, two on Valley Avenue and one on Adams Drive.
Breakfast
Breakfast and coffee in Winchester: Old Town and Pleasant Valley
18 breakfast and coffee stops inside Winchester city limits, most within a few blocks of the Loudoun Street Mall, with hours from each one's own site.
Burgers
Where to get burgers in Winchester: Old Town and the south side
10 places for burgers inside Winchester city limits: seven pubs and grills in Old Town, plus Five Guys and two Wendy's on the south and east sides.
Sushi
Sushi and Asian restaurants in Winchester: Old Town to Valley Avenue
9 sushi, Japanese, Chinese and Thai restaurants inside Winchester city limits, in Old Town, at Apple Blossom Mall and along Pleasant Valley Road.
Ice cream
Ice cream and desserts in Winchester: Old Town and Valley Avenue
6 ice cream, frozen yogurt, doughnut and chocolate shops inside Winchester city limits, on the Loudoun Street Mall, Valley Avenue and Pleasant Valley Road.
Bakeries
Bakeries in Winchester: Old Town, Boscawen Street and Valley Avenue
6 bakeries inside Winchester city limits, from bread and bagels on East Piccadilly Street to pies on West Boscawen Street and doughnuts on Valley Avenue.
James Charles Winery
James Charles Winery Tree Lighting in Winchester: Dec. 5
James Charles Winery's free Christmas tree lighting is 6 to 9 p.m. Saturday, Dec. 5, at 4063 Middle Road, with Santa, live alpacas, hot cocoa and vendors.
Kris Kringle Market
Kris Kringle Market at Belle Grove: Nov. 21-22, 2026
Belle Grove's Kris Kringle Market is Nov. 21-22 in Middletown, with about 100 vendors. Free entry, except $5 for adults from 10 a.m. to noon Saturday.
Last Sunday Market
Last Sunday Market in Winchester: 2026 dates and parking
The Last Sunday Market is 10 a.m. to 2 p.m. Sunday, Nov. 29, at the Exchange on Loudoun on the walking mall, the season's final date. Admission is free.
Thanksgiving Day 5K
Winchester Thanksgiving Day 5K: 2026 race, times and parking
The Thanksgiving Day 5K starts at 8:45 a.m. Thursday, Nov. 26, at Sherando High School, with kids' runs from 8 a.m. There is no race-day registration.
Virginia Gourd Show and Sale
Virginia Gourd Show and Sale in Winchester: Nov. 14-15
The Virginia Gourd Show and Sale is 10 a.m. to 5 p.m. Nov. 14-15 at the Museum of the Shenandoah Valley, 901 Amherst St. Admission to the show is free.
Holiday Craft Show
West Oaks Holiday Craft Show in Winchester: Nov. 28
West Oaks Farm Market's Holiday Craft Show is 9 a.m. to 3 p.m. Saturday, Nov. 28, at 4305 Middle Road, with more than 40 vendors on Small Business Saturday.
The Wickhams: Christmas at Pemberley
Christmas at Pemberley in Winchester: Nov. 13-28 show
"The Wickhams: Christmas at Pemberley" runs Nov. 13-28 at Winchester Little Theatre, 315 W. Boscawen St. Tickets are $25, $23 for seniors, $18 for students.