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

Free Christmas Concert with Valley Chorale

Handley Regional Library 100 W. Piccadilly St., Winchester, VA

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

Christmas Tree Lighting

James Charles Winery 4063 Middle Road, Winchester, VA

Join us for our annual lighting of the winery Christmas tree! Gather around for a spectacular tree lighting with friends and family. We'll have you swaying with good cheer, with LIVE music featuring all your favorite Winter tunes. We're excited to welcome Marie Dana, a local chocolatier. Try her gourmet truffles in flavors like cappuccino, ... Read more

Songs Joy: An Afternoon of Christmas Favorites

First Presbyterian Church 116 S Loudoun St, Winchester, VA

Please join us for "Songs Joy: An Afternoon of Christmas Favorites" with MiKayla Lynn Hatfield and Amy Bowman 2:30pm on December 12. MiKayla has the opportunity to attend the esteemed program American Institute of Musical Studies in Gratz, Austria in the summer of 2022. The recital is to serve as a benefit that will aid ... 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

Holiday Open House at Willow Moon Farm

Willow Moon Farm 1570 Ebenezer Church Road, Gore, VA

We are so excited to announce our ANNUAL OPEN HOUSE here on the farm on December 18th from 10am - 3pm! What can you expect? Our apothecary building open- where we will have all of our products and items that we offer displayed for you to shop, ask questions and talk with Sara (owner) about ... Read more

Christmas Cheer Party

Valerie Hill Vineyard and Winery 1687 Marlboro Road, Stephens City, Virginia

It’s Valerie Hill Vineyard & Winery's annual CHRISTMAS CHEER PARTY! Saturday, December 18th from 6-9pm. Warm mulled wine, the seasonal sounds of holiday music, and of course, wine. That's how we spread Christmas cheer at Valerie Hill! Join us for a special holiday evening of great wines, exclusive food offerings, and holiday fellowship! The Manor ... Read more

The Nutcracker

Patsy Cline Theater at Handley High School 425 Handley Boulevard, Winchester, VA

Please join us for the 40th annual production of THE NUTCRACKER, a Winchester Holiday Tradition Since 1982! Tickets are reserved seating. You are able to select your seats using an interactive seating chart. If you have a special seating request or need help selecting seats, please call 540-665-0343. Tickets may also be purchased by cash ... 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

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