Winchester does it right for the holidays. Take a look at the exciting lineup below, then hop over to VisitWinchesterVA.com for more details and holiday events.
A Christmas Carol
Nov. 7–Dec. 6 • Winchester Little Theatre • 315 W. Boscawen St.
Based on the novel by Charles Dickens, adapted by Lydia Stewart with music and lyrics by Paul Keew. Directed by Sara Gomez; musical direction by Kristal Cutler. Tickets: $18–$25 WinchesterLittleTheatre.org
Garden Lights
Nov. 13–30 • Museum of the Shenandoah Valley • 902 Amherst St., W
Dramatic nighttime lighting display with souvenirs, food, and drinks available for purchase. (Wednesday–Sunday), 5:30 p.m., timed tickets every 30 minutes. Closed Mondays, Tuesdays, and Thanksgiving Day. Tickets: $5 (ages 5–18), $19 (adults); MSV member discount available. Visit TheMSV.org/Garden-Lights
Thanksgiving Organ Concert
Nov. 16, 3 p.m. • Grace Evangelical Lutheran Church • 26 W. Boscawen St.
The Winchester Chapter of the American Guild of Organists presents a Thanksgiving benefit concert for Winchester Area Temporary Transitional Shelter (WATTS) and Winchester Rescue Mission. Admission: Free; donations accepted.
Kris Kringle Market
Nov. 22–23, 10 a.m.–4 p.m. • Belle Grove Plantation • 336 Belle Grove Rd. • Middletown
Holiday market featuring vendor booths with handcrafted treasures, wreath-making classes, locally made food, roaming carolers, and activities for kids of all ages. BelleGrove.org/Calendar/Kris-Kringle
Arts Chorale of Winchester Gloria Concert
Nov. 22, 7 p.m. • First Baptist Church • 205 W. Piccadilly St.
Featuring works by Vivaldi, Rutter, Ames, and Gabrieli with orchestra and soloists. Tickets: $18–$20; children under 12 free ArtsChoraleWinchester.org
Thanksgiving Day 5K and Fun Run
Nov. 27, 8 a.m. • Sherando High School • 185 S. Warrior Dr. • Stephens City
Kick off Thanksgiving Day with fun and fitness in scenic Sherando Park to benefit Winchester Area Temporary Transitional Shelter (WATTS). Kids Fun Run and Tot Trot: 8–8:30 a.m. 5K: 8:45 a.m. Register early; no race day registrations. RunAtTheTop.net/Thanksgiving-Day-5k
Walking in a Winter Wonderland
Nov. 28, 2025–Jan. 1, 5:30–8:30 • Clearbrook Park • 130 Poolside Drive, Clear Brook
Wander an illuminated path with light displays and music, perfect for an evening holiday stroll. Hosted by Frederick County Parks & Recreation. Closed Christmas Eve, Christmas Day, and New Year’s Eve. Timed tickets, admission: $15 at the gate; advance tickets available. TicketsIgnup.io/TicketEvent/WalkingInAWinterWonderland
Belle Grove Holiday Tours
Dec. 5–30 • 2025 Belle Grove Plantation • 366 Belle Grove Road • Middletown
Belle Grove Plantation gets decorated for the holidays, featuring a 12-foot Christmas tree, with each room decorated by area garden clubs, and a “Let Freedom Ring” theme marking the beginning of America’s 250th anniversary in 2026. BelleGrove.org
Abram’s Delight Candlelight Tour
Dec. 5–6, 2025 • Abram’s Delight Museum • 1340 S. Pleasant Valley Rd.
Kick off the holiday season with the annual candlelight tour at Abram’s Delight, Winchester’s oldest house (built in 1754), featuring holiday decorations. Admission: Free WinchesterHistory.org
Winchester Old Town Winter Village
Dec. 5–7, 2025 • Loudoun Street Pedestrian Mall • Historic Old Town Winchester
Historic Old Town Winchester transforms into a cozy holiday market reminiscent of European Christmas markets. Features modern and traditional food and craft vendors, live music, concerts, a special Kinder Village, and holiday-decorated shops. WinchesterWinterVillage.com
Holiday House Tours
Dec. 7, 2025, Noon–4 p.m. • Winchester
Various historic sites in Winchester are beautifully decorated during Preservation of Historic Winchester’s annual Holiday House Tours. Proceeds benefit PHW’s mission to safeguard Winchester’s architectural heritage. Tickets: $30 (advance purchase at Kimberly’s and Winchester-Frederick County Visitors Center); $35 (purchased at tour sites) PHWI.org
Winchester Holiday Lights Trolley Tour • Winchester
Dec. 12–13, 2025 Start: Winchester-Frederick County Visitors Center. Celebrate the season with Winchester’s Holiday Lights Trolley Tour and enjoy the city’s best light displays. Begin with cookies and hot chocolate at the Visitors Center before boarding. One tour Friday, two tours Saturday. Contact: (540) 542-1326
