Leesburg Holiday Events

CHRISTMAS Cake Pop Workshop Class!

The Conche 20 Dec 2025

The Jingle Jam '25

Tally Ho Theater 13 Dec 2025

Holiday Celebration Meetup With Horses and Alpacas

Virk Equestrian Arts LLC 20 Dec 2025

Holiday Cookie Exchange

390 Plaza St. Leesburg, VA 19 Dec 2025

Holiday Dog Cookie Decorating

42225 Adoption Drive, Leesburg, VA, United States, Virginia 16 Dec 2025

PJ Party with Santa

Leesburg Diner 19 Dec 2025

Home for the Holidays - Fee-Waived Adoption Event

42225 Adoption Drive, Leesburg, VA, United States, Virginia 20 Dec 2025

The Amish Outlaws Amazing Holiday Spectacular!

Tally Ho Theater 19 Dec 2025

Ugly Christmas Sweater Contest

49 Catoctin Circle SE, Leesburg, VA 19 Dec 2025

Holiday Wreath and Sip Workshop

48 Fields Farm 14 Dec 2025

Christmas Eve Food & Wine Tasting Menu

32 S King St, Leesburg, VA, United States, Virginia 20175 24 Dec 2025

Silent Night Holiday Paint Event

The Painted Tiger Art Studio 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 14 Dec 2025

"A Born to Run Christmas" with The E Street Shuffle: A Tribute to the Boss

Tally Ho Theater 19 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 The Grinch

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

Creative Painting And Drawing

108 South Street #108 SE, Leesburg, VA 4 Jan 2026

Holiday Celebration | ropes & cookies & gift wrapping

Leesburg, Virginia 19 Dec 2025

Loudoun Cider House Holiday Market

48 Fields Farm 21 Dec 2025

Christmas Village 2025 with Santa and The Grinch

19246 James Monroe Hwy, Leesburg, VA, United States, Virginia 20175 20 Dec 2025

Holiday Centerpiece Workshop with Blooms2U

Fleetwood Farm Winery, Evergreen Mills Rd, Leesburg, VA, USA 20 Dec 2025

Christmas Village 2025 with Santa and friends!

19246 James Monroe Hwy, Leesburg, VA, United States, Virginia 20175 21 Dec 2025

HHS Teacher and Staff Goodie Giveaway

Heritage High School 18 Dec 2025

Summer & Eric at Anchor Bar NOVA

Anchor Bar NOVA 26 Dec 2025

Leesburg Holiday Market

30 Catoctin Circle SE, Leesburg, VA, United States, Virginia 20175 17 Dec 2025

PRO After Hours Holiday Party hosted by TW Perry

Tw Perry 17 Dec 2025

Christmas Village 2025 with Santa and friends!

19246 James Monroe Hwy, Leesburg, VA, United States, Virginia 20175 23 Dec 2025

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

Holy Trinity Lutheran Church 20 Dec 2025

Skate with the Grinch (And Santa)

19201 Compass Creek Pkwy, Leesburg, VA, United States, Virginia 20175 20 Dec 2025

Ugly Sweater Weekend

15669 Limestone School Rd, Leesburg, VA, United States, Virginia 20176 20 Dec 2025

Snowy Christmas Adult and Kids Paint Event

The Painted Tiger Art Studio 20 Dec 2025

Ugly Sweater Party

1602 Village Market Blvd SE #120, Leesburg, VA, United States, Virginia 20175 18 Dec 2025

Landscape Painting Class, 2nd and 3rd grade

108 South Street #108 SE, Leesburg, VA 10 Jan 2026

The Festive Pour: Holiday Sparkling Wines

32 S King St, Leesburg, VA, United States, Virginia 20175 17 Dec 2025

ROB HO-HO-HOEY Live Music at STONE TOWER WINERY (Leesburg, VA)

Stone Tower Winery 26 Dec 2025

FREE Grounding Gentle Yoga Flow for the Holidays

Susan Green Living 22 Dec 2025

Christmas Village 2025 with Santa and friends!

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

Garage Sale in Leesburg

Leesburg Country Club 14 Dec 2025

Breakfast with Santa

The Branch 14 Dec 2025

Dancing Through Time: The Nutcracker Performances from the Loudoun Ballet

Rust Library 22 Dec 2025

Putt & Play

407 East Market Street, Leesburg, VA, United States, Virginia 20176 22 Dec 2025

12 Annual Girl's Holiday Happy Hour & Charity Event For The Kranias Family

Lightfoot Restaurant 17 Dec 2025

Holiday Shopping Fab & Fit @ Misguided Angels

14 S King Street, Leesburg, VA 12 Dec 2025

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

Leesburg Corner, Leesburg, Virginia 20 Dec 2025