Leesburg Holiday Events

80s Night - The Reagan Years at Tally Ho

Tally Ho 4 Oct 2025

The Amish Outlaws Amazing Holiday Spectacular!

Tally Ho Theater 19 Dec 2025

M**der Mystery Dinner

The Branch 16 Oct 2025

WATERCOLOR HOLIDAY CARDS

Casanel Vineyards and Winery 15 Nov 2025

The Amish Outlaws Amazing Holiday Spectacular!

Tally Ho Theater 20 Dec 2025

Brighton Fall Focus Trunk Show

212 Catoctin Cir SE Ste C, Leesburg, VA, United States, Virginia 20175 30 Sep 2025

CHRISTMAS Cake Pop Workshop Class!

The Conche 20 Dec 2025

Holiday Wine Cork Decorations

Casanel Vineyards and Winery 15 Nov 2025

Giant Bunny Meet & Greets @ Hogback Mountain

Hogback Mountain Pony Rides, LLC 18 Oct 2025

Thanksgiving Wine Festival

1605 Village Market Blvd SE, Leesburg, VA, United States, Virginia 20175 8 Nov 2025

Monthly Harper Park PTA Meeting (date moved due to holiday)

701 Potomac Station Drive, Leesburg, VA, United States, Virginia 20176 14 Oct 2025

Holiday Arts and Crafts Show, hosted by Senior Center Advisory Board

102 North Street NW Suite B, Leesburg, VA, United States, Virginia 20176 6 Dec 2025

Holiday Arts and Crafts Show, hosted by the Senior Center Advisory Board

102 North Street NW Suite B, Leesburg, VA, United States, Virginia 20176 5 Dec 2025

Lucketts Holiday House November 20th-23rd

The Old Lucketts Store 20 Nov 2025

Pre-Christmas New York City Day Trip I (Transportation Only)

Leesburg Corner, Leesburg, Virginia 20 Dec 2025