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.

Last checked Oct. 18, 2026. Updated each year. The 2026 date comes from Winchester Parks and Recreation; the route, closures and parking are from the 2025 parade listing until the city posts this year’s.

Winchester’s Holiday Parade is at 7 p.m. Monday, Nov. 30, 2026, followed by the traditional tree lighting, the city’s Parks and Recreation department says. It is a nighttime parade through downtown, and it is free to watch.

Who to call

Route and tree lighting

The city has not yet posted the 2026 route. Last year’s parade, on Monday, Dec. 1, 2025, ran:

  • Piccadilly Street from Cameron Street to Braddock Street
  • Braddock Street to Cork Street
  • Cork Street from Braddock Street back to Cameron Street

Right after the parade, the crowd moved to the walking mall in front of the Old Court House Civil War Museum for the official tree lighting, with music and a visit from Santa. In 2025 the parade was presented by Winchester Parks and Recreation with Wawa and streamed live on WinLife TV’s YouTube channel.

Road closures and parking (2025)

From the 2025 listing; we will update this when the city posts 2026 details:

  • Road closures began at 5:30 p.m.
  • The Braddock Auto Park closed at 5:30 p.m. and reopened after the parade. Cars inside could not leave while it was closed.
  • The Court Square Auto Park entrance on Cameron Street was closed; the Kent Street entrance stayed open. Regular parking fees applied.

See our getting around guide for downtown parking.

Entering the parade

Businesses, community groups, schools, churches, bands, performance groups, clubs and float builders can apply online:

  • Deadline: noon Monday, Nov. 2.
  • Entry fee: $15. Applications after the deadline pay a $10 late fee and are not guaranteed.
  • Nothing received after noon Monday, Nov. 9, will be considered.

More holiday events downtown

  • Festival of Trees, Saturday, Nov. 21, at the Youth Development Center, 302 S. Loudoun St., with decorated trees and wreaths to bid on and local vendors. Details.
  • Winchester Old Town Winter Village, Dec. 4-6, a European-style holiday market of food and craft vendors on the pedestrian mall. The weekend schedule had not been posted. Winter Village.
  • Phil Kline’s Unsilent Night, Saturday, Dec. 12. Meet at 5:30 p.m. on the walking mall for instructions; the walk with music on phones and boom boxes starts at 6 p.m. and lasts about 45 minutes. Details.
  • “The Wickhams: Christmas at Pemberley,” Nov. 13-28, at Winchester Little Theatre, 315 W. Boscawen St. Details.

What this means for you

  • Mark Monday, Nov. 30, at 7 p.m. It is a weeknight parade.
  • Expect downtown streets to close from about 5:30 p.m., and do not park in a garage that will be locked until the parade ends.
  • Float and group entries are due by noon Nov. 2.

More: things to do this month.

Frequently asked questions

When is the Winchester Christmas parade in 2026?

The city’s Holiday Parade is at 7 p.m. Monday, Nov. 30, 2026, followed by the traditional tree lighting, according to Winchester Parks and Recreation.

What is the Winchester Christmas parade route?

The city has not posted the 2026 route yet. In 2025 the parade ran on Piccadilly Street from Cameron to Braddock, Braddock Street to Cork, and Cork Street from Braddock to Cameron.

Where is the Winchester tree lighting?

In 2025 the tree was lit on the walking mall in front of the Old Court House Civil War Museum immediately after the parade, with music and a visit from Santa.

How do I enter a float in the Winchester holiday parade?

Apply online through Winchester Parks and Recreation by noon Monday, Nov. 2. The entry fee is $15; late entries pay $10 more, and nothing is accepted after noon Nov. 9.