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.

Last checked Oct. 19, 2026. This page is updated each year at the same address. Store hours and dates come from each center’s or organizer’s own page; we list no prices or deals.

Black Friday is Nov. 27, 2026, and Small Business Saturday is Nov. 28. Winchester’s holiday shopping splits between Apple Blossom Mall on the city’s south side and the independent shops of Old Town on the Loudoun Street Mall, with craft and maker markets in the countryside around the city.

Who to call

  • Apple Blossom Mall: 1850 Apple Blossom Drive, hours page
  • Old Town shops: Friends of Old Town shop directory
  • Downtown parking: Winchester Parking Authority, 540-722-7575
  • Traffic or a crash: Winchester Police non-emergency, 540-662-4131; emergency, 911

Holiday weekend at a glance

Date What Where
Saturday, Nov. 21 Festival of Trees Youth Development Center, 302 S. Loudoun St.
Thursday, Nov. 26 Thanksgiving; free meter parking Downtown
Friday, Nov. 27 Black Friday; free meter parking Downtown and Apple Blossom Mall
Saturday, Nov. 28 Small Business Saturday Old Town
Sunday, Nov. 29 Museum Store Sunday, 10 a.m. to 5 p.m. Museum of the Shenandoah Valley
Monday, Nov. 30 Holiday Parade, 7 p.m. Old Town
Dec. 5-6 Winchester Winter Village Loudoun Street Mall

Apple Blossom Mall

Apple Blossom Mall, 1850 Apple Blossom Drive, is the city’s enclosed mall, run by Simon. Its regular hours are 10 a.m. to 8 p.m. Monday to Saturday and 11 a.m. to 6 p.m. Sunday. The mall had not posted Thanksgiving or Black Friday hours when we checked on Oct. 19, and individual stores and the AMC theater keep their own hours. We will add the 2026 holiday hours when they are posted.

Old Town and Small Business Saturday

The Loudoun Street Mall, the brick pedestrian street in Old Town, is the city’s main cluster of independent shops: bookstores, toy stores, boutiques, galleries and gift shops. Friends of Old Town, the downtown Main Street group, keeps a shop directory and in 2025 published a holiday shopping guide (PDF).

On Black Friday 2025 the Winchester Book Gallery marked Plaid Friday, a shop-local day for independent businesses (2025 listing). A 2026 date had not been posted.

Parking: The Winchester Parking Authority lists Thanksgiving Day and the Friday after Thanksgiving as free parking at meters. Meters are also free on weekends. The four covered autoparks (Braddock, Court Square, Loudoun and George Washington) are open 24 hours and charge their regular hourly rates.

Holiday markets

  • Winchester Winter Village, Saturday and Sunday, Dec. 5-6. Friends of Old Town and the visitors bureau turn the pedestrian mall into a European-style holiday market of food and craft vendors, with live caroling, seasonal refreshments and horse-drawn wagon rides on Saturday. The event site says the schedule is coming soon. In 2025 a second market of vendors set up at the south end of the mall from noon to 6 p.m. Saturday and noon to 4 p.m. Sunday.
  • Festival of Trees, Saturday, Nov. 21, 10 a.m. to 9 p.m. at the Youth Development Center, 302 S. Loudoun St., with decorated trees and wreaths and local vendors (listing).
  • Museum Store Sunday, Nov. 29, 10 a.m. to 5 p.m. at the Museum of the Shenandoah Valley, 901 Amherst St., with local vendors and artisans in the Museum Store (museum events).

Last year’s craft shows (2026 dates not yet posted)

  • Kris Kringle Market at Belle Grove, Middletown: Nov. 22-23, 2025, 10 a.m. to 4 p.m., with vendors, carolers and children’s activities (2025 listing).
  • Shenandoah Potters Guild Holiday Pottery Show: Thanksgiving weekend, Nov. 29-30, 2025, at the Hazel-Pruitt Armory (The HIVE) at Shenandoah University, 1460 University Drive, 10 a.m. to 4 p.m. (2025 listing; guild site).
  • Holiday Craft Show at West Oaks Farm Market, 4305 Middle Road: Saturday, Nov. 29, 2025, 9 a.m. to 3 p.m., with more than 40 vendors (2025 listing).
  • ShenArts Holiday Market, ShenArts Gallery, 128 N. Loudoun St.: opened Dec. 5, 2025, with work by more than 50 local artists (2025 listing).
  • Christmas Maker’s Market at The Homestead Farm at Fruit Hill Orchard, 2502 N. Frederick Pike: Saturday, Dec. 6, 2025, 10 a.m. to 3 p.m., free admission (2025 listing).

We will replace these with 2026 dates as each organizer posts them.

Traffic and parking notes

  • The Holiday Parade closes downtown streets on the evening of Monday, Nov. 30. In 2025 closures began at 5:30 p.m. and the Braddock Autopark closed during the parade; see our Christmas parade page.
  • Road work that affects the trip to the mall is on our road construction and closures page.

What this means for you

  • Check Apple Blossom Mall’s hours page the week of Thanksgiving; holiday hours were not out in mid-October.
  • Shop Old Town on Black Friday to use free meter parking.
  • Save Dec. 5-6 for Winter Village.

Related: Thanksgiving in Winchester, holiday lights and Christmas events and new businesses.

Frequently asked questions

What are Apple Blossom Mall’s hours on Black Friday 2026?

The mall had not posted holiday hours when we checked on Oct. 19. Its regular hours are 10 a.m. to 8 p.m. Monday to Saturday and 11 a.m. to 6 p.m. Sunday; check the mall’s hours page the week of Thanksgiving.

Is parking free in Old Town Winchester on Black Friday?

Yes, at the meters. The Winchester Parking Authority lists Thanksgiving Day and the Friday after Thanksgiving as free meter parking holidays. The four city garages charge their usual rates.

When is Winter Village in Winchester in 2026?

Friends of Old Town lists Winchester Winter Village for Saturday and Sunday, Dec. 5-6, 2026, on the Loudoun Street Mall, with horse-drawn wagon rides on Saturday. The full schedule had not been posted.

Where is Small Business Saturday shopping in Winchester?

Old Town Winchester’s Loudoun Street Mall is the main cluster of independent shops; Friends of Old Town keeps a shop directory and published a holiday shopping guide in 2025.