Walking in a Winter Wonderland

Clearbrook Park 130 Poolside Drive, Clear Brook, VA

November 26-January 2 You’ll be delighted by this light show that lets you see fantastic displays and music along the paved path at Clearbrook Park. Take your time enjoying the sights and sounds of the season along the magical stroll through a winter wonderland. Clearbrook Park’s annual light show is a tradition sure to create ... Read more


Holiday Tours at Belle Grove

Belle Grove Plantation 336 Belle Grove Rd., Middletown, VA

Belle Grove Plantation will be decorated for the holidays! In the historic Manor House, there will be a 12-foot Christmas tree in the Parlor and area Garden Clubs will adorn each room inspired by "Timeless Tales & Verse" and featuring holiday themed literature from the years of Belle Grove's history. Belle Grove will be open ... Read more

Glory Bea: A Shenandoah Christmas Story

Lord Fairfax Community College 173 Skirmisher Lane, Middletown, VA

Selah Theatre Project presents: GLORY BEA: A Shenandoah Christmas Story GLORY BEA: A Shenandoah Christmas Story, by Rich Follett and Larry Dahlke, set in the 1930's in the Shenandoah Valley and the Depression has hit the valley residents. The return of the Wayside Theatre holiday favorite is being presented by Selah Theatre Project, in partnership ... Read more

Free Christmas Concert with Valley Chorale

Grace United Methodist 7882 Main Street, Middletown, Virginia

Join the Valley Chorale for our *free* Christmas concerts on December 10, 11 and 12 in Middletown, Winchester and Front Royal, respectively. This year's concerts feature classical, sacred and popular selections, sure to lift your spirits! All concerts are free-of-charge. Seating is limited…arrive early! COVID safety: all Valley Chorale personnel are fully vaccinated and will ... Read more

Breakfast with Santa

George Washington Hotel 103 East Piccadilly, Winchester, VA

Santa Claus is coming to town 🎅 Join us for Breakfast with Santa in The Grand Ballroom on Saturday, December 11th! Seatings at 8:30 am or 11:30 am Adults (10 Years & Older) | $35 2 - 9 Year Olds | $25 Under 2 | Free Email emily@wyndhamwinchester.com for reservations. For more information

Holiday Open House

War Memorial Building 1001 E. Cork Street, Winchester, VA

Fun festivities for the whole family! - Kids Crafts with Childcare - Reindeer Games with Athletics - Adult Fitness Classes set to holiday music - Gingerbread House Creation with Community Rec (free, but preregistration required) - Ornament Decorating with Community Rec - Elf Scavenger Hunt with Facilities - Raffles with Winchester Parks Foundation - Breakfast ... Read more

Holiday Market at Richards Fruit Market

Richard’s Fruit Market 6410 Middle Road, Middletown, VA

Make plans to attend our holiday market on December 11th from 10am - 2pm. We'll have hot apple cider, caramel apples, market made vegetable soup and ALL your market favorites (including Christmas pies!) Plus we've got lots of great items from our local small businesses AND photos with our Christmas calf with Jaime Lyn Photography ... Read more

Holiday Maker’s Market

The Homestead Farm at Fruit Hill Orchard 2502 N. Frederick Pike, Winchester, Virginia

Support Local this season by shopping The Homestead Farm's Holiday Maker's Market! The event will be held outdoors, and will feature local vendors, live music, fresh cut Christmas trees and wreaths, baked goods, hot cocoa, and more!

Donuts with Santa

Marker-Miller Orchards 3035 Cedar Creek Grade, Winchester, VA

Santa is taking time out of his busy schedule to stop by for a visit. He will be here from 11:00-2:00, so don't forget to bring your camera. While Santa's here we will be serving hot chocolate and apple cider donut holes. This is a free event, so all ages are welcome to come and ... Read more

Holiday Open House

Old Town Winchester 1 North Loudoun Street, Winchester, VA

The Holiday Open House is an all-day event starting at the War Memorial Building/Recreation Center (1001 E Cork St, Winchester), from 9-11am, with activities for adults and children leading up to the arrival of Santa. At 11am, follow Santa on his firetruck down to Old Town for photos and fun on the Loudoun Street Pedestrian ... Read more

Click here to view more upcoming events on our Winchester VA Events Calendar.