Leesburg Holiday Events

CHRISTMAS Cake Pop Workshop Class!

The Conche 20 Dec 2025

Farmer John’s Holiday Market

15520 James Monroe Highway, Leesburg, VA 6 Dec 2025

Santa's Workshop 2025

Fleetwood Farm Winery 6 Dec 2025

Christmas Village 2025 with Santa and The Grinch

19246 James Monroe Hwy, Leesburg, VA, United States, Virginia 20175 13 Dec 2025

Mistletoe Market

Loudoun County Courthouse grounds 6 Dec 2025

Leesburg Christmas and Holiday Parade

60 Ida Lee Dr NW, Leesburg, VA 20176-2224, United States 13 Dec 2025

Christmas Village 2025 with Santa and The Grinch

19246 James Monroe Hwy, Leesburg, VA, United States, Virginia 20175 12 Dec 2025

The Jingle Jam '25

Tally Ho Theater 12 Dec 2025

Billyville @ King’s Court

The King's Court Tavern 6 Dec 2025

Loudoun Thrift x Blue Ridge Care Holiday Private Shopping Event

Blue Ridge Hospice Leesburg Thrift Shop 23 Nov 2025

From the Vault: Under the Tree

16 Loudoun St SW, Leesburg, VA, United States, Virginia 20175 6 Dec 2025

Holiday Market

19925 Hogback Mountain Rd, Leesburg, VA, United States, Virginia 20175 28 Nov 2025

Craftail Presents: "Bleu Chistmas" at Bleu Frog Vineyards

Bleu Frog Vineyards & Ole Bleu Brewery 13 Dec 2025

Rad Red & Friends at Loudoun Kitchen & Bar Supporting LCFR Heros for the Holidays Toy Drive!!!

The Loudoun Kitchen & Bar 28 Nov 2025

Holiday Themed Trivia

1609 Village Market Bld SE, Leesburg, VA, United States, Virginia 20175 25 Nov 2025

Loudoun Chorale Winter Concert: Glorias Large and Small

835 Lee Ave SW, Leesburg, VA, United States, Virginia 20175 6 Dec 2025

St Nikolaus Brunch to Benefit Veterans

Black Hoof Brewing Company 13 Dec 2025

Songs of Light and Wonder - Christmas Concert (3/4)

Holy Trinity Lutheran Church 20 Dec 2025

Craftails Presents: Christmas Balls and Beer!

Black Hoof Brewing Company 9 Dec 2025

Holidays in Leesburg Fine Arts & Crafts Show

60 Ida Lee Dr NW, Leesburg, VA, United States, Virginia 20176 6 Dec 2025

Christmas Village 2025 TREE LIGHTING- with Santa and the Grinch

19246 James Monroe Hwy, Leesburg, VA, United States, Virginia 20175 6 Dec 2025

Christmas Village 2025 - with Santa and the Grinch

19246 James Monroe Hwy, Leesburg, VA, United States, Virginia 20175 5 Dec 2025

Christmas Village 2025 with Santa and our friend Shorty - the Highland Cow!

19246 James Monroe Hwy, Leesburg, VA, United States, Virginia 20175 14 Dec 2025

Loudoun Fairfax Hounds Holiday Hunt Ball

Birkby House 13 Dec 2025

Leesburg Nativity Tour at the Leesburg Christmas Parade

Ida Lee Dr NW, Leesburg, VA 20176, United States 13 Dec 2025

Christmas Village 2025 with Santa and The Grinch

19246 James Monroe Hwy, Leesburg, VA, United States, Virginia 20175 19 Dec 2025

Marshall Plan Tree Walk Lighting Ceremony

312 E Market Street, Leesburg, VA, United States, Virginia 20176 6 Dec 2025

Travinia's Breakfast with Santa

1605 Village Market Blvd SE, Leesburg, VA, United States, Virginia 20175 13 Dec 2025

Davis Mansion Holiday Tours

17195 Southern Planter Ln, Leesburg, VA 21 Nov 2025

Heritage Arts and crafts Show

Heritage High School 22 Nov 2025

Loudoun Chorale Winter Concert: Glorias Large and Small

835 Lee Ave SW, Leesburg, VA, United States, Virginia 20175 7 Dec 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

Holly Jolly Skate Night

407 East Market Street, Leesburg, VA, United States, Virginia 20176 19 Dec 2025

Christmas Village 2025 with Santa and our friend Shorty - the Highland Cow!

19246 James Monroe Hwy, Leesburg, VA, United States, Virginia 20175 7 Dec 2025

PRO After Hours Holiday Party hosted by TW Perry

Tw Perry 17 Dec 2025

The 703 Holiday Bazaar

Village Pickle 13 Dec 2025

10 Year RUNiversary & Holiday Party

Black Hoof Brewing Company 6 Dec 2025

Naughty or Nice Holiday Bash

Fleetwood Farm Winery, Evergreen Mills Rd, Leesburg, VA, USA 11 Dec 2025

Christmas Eve Food & Wine Tasting Menu

32 S King St, Leesburg, VA, United States, Virginia 20175 24 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

Breakfast with Santa

The Branch 14 Dec 2025

Holiday Arts and Craft Show - 3rd Annual!

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

Holiday Concert

Douglass Community Center 13 Dec 2025

Loudoun Cider House Holiday Market

48 Fields Farm 21 Dec 2025

The Amish Outlaws Amazing Holiday Spectacular!

Tally Ho Theater 19 Dec 2025

Christmas Village 2025 with Santa and friends!

19246 James Monroe Hwy, Leesburg, VA, United States, Virginia 20175 22 Dec 2025

Business Women of Loudoun Holiday Social

River Creek Club (Leesburg, VA) 4 Dec 2025

Chime In! A Holiday Concert

The Senior Center of Leesburg 9 Dec 2025

Putt & Play

407 East Market Street, Leesburg, VA, United States, Virginia 20176 22 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