Christmas 2026 in Winchester: Winter Village Dec. 5-6, Unsilent Night, museum holiday concerts, the Clearbrook light walk and where to see Santa.

Last checked Oct. 19, 2026. This page is updated each year at the same address. Where an organizer has not posted its 2026 dates, we say which year a date is from and never guess the new one.

Looking for the parade? The city’s Holiday Parade is at 7 p.m. Monday, Nov. 30, followed by the tree lighting in Old Town; route, parking and entries are on our Christmas parade and tree lighting page. This page covers the light displays, Santa visits, holiday markets, concerts and Hanukkah.

Who to call

  • City events: Winchester Parks and Recreation, 540-662-4946
  • Museum of the Shenandoah Valley box office: 540-662-1473
  • Winter Village and Old Town events: Friends of Old Town
  • Beth El Congregation: 520 Fairmont Ave., 540-667-1889

Confirmed for 2026

Date Event Where
Nov. 13-28 “The Wickhams: Christmas at Pemberley” Winchester Little Theatre, 315 W. Boscawen St.
Saturday, Nov. 21 Festival of Trees, 10 a.m. to 9 p.m. Youth Development Center, 302 S. Loudoun St.
Monday, Nov. 30 Holiday Parade and tree lighting, 7 p.m. Old Town
Dec. 4-12 Hanukkah Begins at sundown Dec. 4
Saturday, Dec. 5 Holiday door swag workshop Museum of the Shenandoah Valley
Dec. 5-6 Winchester Winter Village Loudoun Street Mall
Saturday, Dec. 12 Unsilent Night, 5:30 p.m. Loudoun Street Mall
Sunday, Dec. 13 Yesterday Swing Orchestra holiday concert, 1 or 3 p.m. Museum of the Shenandoah Valley
Tuesday, Dec. 15 Holiday Tea Museum of the Shenandoah Valley
Thursday, Dec. 17 Jackson Caesar holiday concert, 3:30 or 6 p.m. Museum of the Shenandoah Valley
Friday, Dec. 25 Christmas City yard waste canceled

Holiday markets in Old Town

Winchester Winter Village, Saturday and Sunday, Dec. 5-6. Friends of Old Town and the visitors bureau set up a European-style market of food and craft vendors on the pedestrian mall, with live caroling and music, seasonal refreshments and horse-drawn wagon rides on Saturday. The full schedule was “coming soon” on the Winter Village site, which also publishes an annual Christmas lights guide to standout neighborhoods and homes.

Festival of Trees, Saturday, Nov. 21, at the Youth Development Center: decorated trees and wreaths and local vendors (listing).

More markets and store hours are on our Black Friday and holiday shopping page.

Light displays (2025 dates; 2026 not yet posted)

  • Walking in a Winter Wonderland, Clearbrook Park, 130 Poolside Drive, Clear Brook. Frederick County Parks and Recreation’s half-mile paved path of light displays and a light show set to music ran Nov. 28, 2025, to Jan. 1, 2026, with timed entry from 5:30 p.m. It closed Christmas Eve, Christmas Day and New Year’s Eve, and tickets were sold online ahead (2025 tickets page; 2025 listing).
  • Garden Lights, Museum of the Shenandoah Valley, 901 Amherst St. Lights, lasers and a thousand LED flowers in the formal gardens ran Nov. 13-30, 2025, Wednesday to Sunday with timed entries every 30 minutes from 5:30 p.m. The route is about two-thirds of a mile (Garden Lights page). The museum’s 2026 events calendar did not list Garden Lights when we checked.
  • Holiday Lights Trolley Tour. The visitors bureau ran trolley tours of local light displays from the Visitors Center, 1400 S. Pleasant Valley Road, on Dec. 12-13, 2025; tickets went on sale Nov. 17 and sold out (2025 listing).

Santa visits

  • Holiday Parade, Monday, Nov. 30. In 2025 the tree lighting after the parade came with a visit from Santa (our parade page).
  • Santa Express (2025: Saturday, Dec. 13). Santa sat inside a caboose along Piccadilly Street at the Timbrook Public Safety Center, 231 E. Piccadilly St., from noon to 5 p.m., with carolers and a Toys for Tots drop-off, on the same day as the Old Town Santa’s Express Cookie Crawl (2025 listing).
  • Pictures with Santa at West Oaks Farm Market, 4305 Middle Road (2025: Saturday, Dec. 13, 10 a.m. to 12:30 p.m.); pets welcome, bring your own camera (2025 listing).

Candlelight and historic houses (2025 dates)

  • Abram’s Delight Candlelight Tour, 1340 S. Pleasant Valley Road: free tours of the 1754 house and grounds decorated by local garden clubs, Dec. 5, 2025, 6 to 8 p.m., and Dec. 6, 3 to 7 p.m. (2025 listing).
  • Belle Grove, Middletown: the manor house was decorated for the holidays Dec. 5-30, 2025 (2025 listing).

Music, theater and tea

  • Unsilent Night, Saturday, Dec. 12. Meet on the walking mall at 5:30 p.m.; the walk with music played on phones and speakers starts at 6 p.m. (listing).
  • Museum of the Shenandoah Valley (events): Yesterday Swing Orchestra, Sunday, Dec. 13, at 1 or 3 p.m.; Holiday Tea with The Tea Cart, Tuesday, Dec. 15, 11 a.m. to 1 p.m. or 3 to 5 p.m.; Jackson Caesar, Thursday, Dec. 17, at 3:30 or 6 p.m.; and a Stuffed Animal Sleepover in the Glen Burnie House, drop-off Friday, Dec. 11, 3 to 5 p.m.
  • “The Wickhams: Christmas at Pemberley,” Nov. 13-28, Winchester Little Theatre (details).
  • “The Nutcracker.” Vostrikov’s Academy of Ballet has staged it every December since 1982; the 44th production, with more than 150 dancers, ran Dec. 13-14, 2025, at the Patsy Cline Theatre at John Handley High School (2025 listing; ballet site).

Hanukkah

Hanukkah 2026 begins at sundown Friday, Dec. 4, and ends at nightfall Saturday, Dec. 12. No public menorah lighting in Winchester had been announced when we checked. Beth El Congregation, 520 Fairmont Ave., is the city’s synagogue; call 540-667-1889.

Christmas week services

  • The city cancels yard waste on Christmas Day, Friday, Dec. 25; trash and recycling run on their normal days (holiday schedule).
  • Downtown parking meters are free on Christmas Eve and Christmas Day (Parking Authority).
  • Winchester Parks and Recreation runs its No School Days program Dec. 28-30, 8 a.m. to 5 p.m., for Winchester Public Schools students ages 5 to 12; register by the Monday before (childcare page).

What this means for you

  • Dec. 5-6 is the big Old Town weekend: Winter Village and the wagon rides.
  • Watch Clearbrook Park and the MSV for 2026 light dates; both sell timed, limited tickets, and the museum says popular time slots sell out quickly.
  • Book the museum’s concerts and tea early; seats are limited.

Related: New Year’s Eve in Winchester, things to do this month and kids’ activities.

Frequently asked questions

Where can I see Christmas lights in Winchester, Virginia?

The biggest display is Frederick County’s Walking in a Winter Wonderland, a half-mile lighted path at Clearbrook Park, which ran Nov. 28, 2025, to Jan. 1, 2026. The Museum of the Shenandoah Valley’s Garden Lights ran Nov. 13-30 in 2025. Neither had posted 2026 dates on Oct. 19.

When is Winter Village in Old Town Winchester?

Friends of Old Town lists Winchester Winter Village for Dec. 5-6, 2026, on the Loudoun Street Mall, with vendors both days and horse-drawn wagon rides on Saturday.

Where can kids see Santa in Winchester?

In 2025 Santa visited the tree lighting after the city’s Holiday Parade; this year’s parade is at 7 p.m. Monday, Nov. 30. In 2025 Santa also sat in a caboose on Piccadilly Street for the Santa Express on Dec. 13; the 2026 date had not been posted.

When is Hanukkah in 2026?

Hanukkah begins at sundown Friday, Dec. 4, 2026, and ends at nightfall Saturday, Dec. 12. Winchester’s synagogue is Beth El Congregation, 520 Fairmont Ave., 540-667-1889.