Holiday Open House & Winter Market

Join us for your new favorite holiday tradition!

Winter in Old Town Winchester is about to get a bit more magical as we bring back the Holiday Open House with a better-than-ever update. From noon to 5pm on Saturday, December 10th, you can come shop all your favorite Old Town businesses with Old Town Spirit in effect–which means you can buy a toasty grown-up hot cocoa or a classic mulled wine to keep your hands warm and your heart aglow! We’ll also have a free gift wrapping station to get all of your purchases packaged up for you, live music and entertainment, and an open-air market along Boscawen St. with vendors and family-friendly activities everyone can enjoy.

The Winchester Winter Market will be taking place at the Feltner Lot on the corner of Loudoun & Boscawen St, with additional vendors placed along the Loudoun St. Walking Mall. There will be plenty to see and stroll, and with Old Town Spirit in effect you can grab a drink from any Old Town establishment to keep warm while you shop. Don’t forget to stop in at all the Old Town businesses as well!

The Children’s Wonderland located at the Civil War Museum/Old Courthouse lawn will feature a heated tent with visits from Santa and the Grinch, as well as free family-friendly activities, arts & crafts, a magical winter photo booth–no child will leave empty-handed!

Free Gift Wrapping will be offered at the Splash Pad on S. Loudoun St. as a courtesy to all Old Town shoppers! Bring your purchases from the Market or any Old Town business and we’ll bag or wrap them up for you on-site!

The following vendors will be onsite at the market:

  • The Ivy Chest
  • Still Meadow Boutique
  • Sage & Co.
  • The Quirky Closet
  • Panhandle Apotheca
  • Jen White
  • Anna Schloemer Designs
  • Cakes by Ashton
  • All the Pretty Bling
  • Tim’s Tiny Trees
  • Halo Apothecary
  • Beth Sisk, Mary Kay Consultant
  • Ifind4you
  • The Fractal Faerie
  • Sunrise Sweets & Treats
  • Woodchuckers Woodworks LLC
  • Lou’s Craft Corner
  • Mermaid & Muse
  • Anything by Ashley
  • Feathered Friends
  • Mama Llama Cookies
  • It’s About Time!
  • Plunder Designs
  • Munolu
  • Author Hannah CR
  • Mimi’s Spun Sugar
  • The Classy Caboose Food Truck
  • Melannic Design
  • Craft du Jour
  • The Irish Peddler
  • Bowls by Adrian
  • VA Kettlecorn
  • Tantalizing Timber
  • Old Valley Pike Soap Company
  • Custom Canvas Creations
  • Mouse Loves Pig
  • Sturgill Photography
  • Malabella Jewelry
  • Scentsy
  • MRC Folk Art
  • Creations of Genesis

For more information on the market, click here.

For more information on Old Town Spirit, click here.

The Santa Crawl benefitting Froggy’s Closet and the Evans Home will also be taking place from 12-9PM with local restaurants, breweries, and bars participating! Wristbands are $10 each and can be purchased on the day of the event at 17 E Boscawen St for access to awesome raffle prizes, amazing discounted holiday drink and food specials, and much more–all entry proceeds go directly to our local charities!

The following Old Town businesses are participating:

  • Benny Meleto’s
  • Broken Window Brewing Co.
  • Dividing Creek Beer Co
  • El Centro Classic Mexican Food & Drink
  • Ellie’s Irish Pub Winchester
  • Macado’s (121 N Loudoun St, Winchester, VA)
  • Piccadilly’s Public House and Restaurant
  • Roma Old Town Wood-Fired Pizzeria
  • Santa’s Library Pop up bar
  • Sexi-Mexi Burritos
  • 50/50 Taphouse
  • The Wine Room at Taylor Pavilion
  • Village Square Restaurant and V2 Oyster Bar & Lounge
  • Vibrissa Beer
  • Water Street Kitchen
  • Willie Sutton’s
  • Winchester Brew Works


The Monument VA will be offering discounted concert tickets with showing proof of wristband at entry- first come, first serve until concert sells out! Concert starts at 9pm!


For information on the Santa Crawl and charity drive, click here.

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