Holiday Open House

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 Mall, with live music, holiday shopping specials, art displays, holiday crafts, and more!

Schedule of events

– 11:30am, Santa arrives downtown
– 11:30am-1pm, Billy Thompson Group @ Taylor Pavilion
– 12-2pm, Santa & Mrs. Claus walk the mall
– 12-5pm, free gift wrapping @ Taylor Pavilion
– 1pm, Winchester Little Theater carolers @ Taylor Pavilion
– 2pm, Sing! Shenandoah carolers @ Taylor Pavilion
– 2-4pm, Gingerbread Jamboree @ Handley Library
– 3pm, Holiday Concert @ Museum of the Shenandoah Valley
– 3-5pm, Holiday Chorale Concert @ Handley Library
– 5-10pm, Old Town Spirit in effect (alcoholic beverages purchased in businesses may be carried outdoors and into other establishments where allowed by merchants)

Bough and Dough Shop

The Bough & Dough Shop, located on the first floor of the Hexagon House, is a boutique-style holiday gift shop featuring talented local artisans. You will find unique handmade items, freshly baked goods, as well as a selection of freshly-cut greenery, wreaths, and premade bows for your holiday decorating.

The shop will feature pottery, art glass, handwoven baskets, unique handcrafted gifts, ornaments, artwork, and books on local history.

Purchases will help support Preservation of Historic Winchester’s mission to preserve the best of the area’s past.

Hours of Operation:
10 AM – 5 PM
Admission: FREE

Shopping is also available online and by pre-order.

Learn more about the shop and its wares or follow our Bough and Dough Shop Instagram.

Holiday Market

Mark your calendars for December 14 when the Old Town Farmers Market will return to the Loudoun Street Mall for a one day Holiday Market as part of our annual Holly Jolly Celebration!

We expect to have market vendors with in-season produce, meats, canned items and the like, seasonal greenery and agricultural products, as well as artisan vendors with locally handmade items.

Interested in participating as a vendor for the Holiday Market? Applications are now available. Apply now!

Plaid Friday and Shop Small Saturday

Escape the crazy hustle and bustle of the big box stores this year and shop local! Bring your friends and spend the day browsing the shops in Old Town for gifts that are truly unique.

Grab a cup of coffee, have a glass of wine, or enjoy lunch at one of Old Town’s restaurants. Gift certificates to local restaurants or breweries are also a great idea!

On this special weekend, shops will be offering special promotions, including a Shopping Passport. Pick up your Shopping Passport from a participating business in Old Town.

More information

Plaid Friday – Nov. 29

Shop Small Saturday – Nov. 30