56 upcoming listings — live music, theater, markets, drag, comedy and more, each with a time, a venue and a street address.
What's coming up
Leesburg Saturday Farmers Market Sat 8 Aug 2026, 8:00 AM — Market Virginia Village Shopping Center · 30 Catoctin Cir SE, Leesburg, VA 20175 · Free entry
Comedy Night in Leesburg presented by the DC Improv Fri 4 Sep 2026, 6:30 PM — Comedy Tally Ho Theater · 19 W Market St, Leesburg, VA 20176 · 18+
Mommy & Me Cake Pop Making Workshop Sat 5 Sep 2026, 10:00 AM — class The Conche · 1605 Village Market Boulevard Southeast, Leesburg, VA 20175
The Super 70's Rock Show featuring Super Trans AM and The Darby Brothers Sat 5 Sep 2026, 6:00 PM — Live music Tarara Winery · 13648 Tarara Lane, Leesburg, VA 20176
Urgent: Foreigner Tribute Sat 5 Sep 2026, 7:00 PM — Live music Tally Ho Theater · 19 W Market St, Leesburg, VA 20176 · 18+
Ugly Kid Joe w/ Wheatus, Platinum Moon Thu 10 Sep 2026, 6:30 PM — Live music Tally Ho Theater · 19 W Market St, Leesburg, VA 20176 · 18+
Winslow (Eagles Tribute) Fri 11 Sep 2026, 7:00 PM — Live music Tally Ho Theater · 19 W Market St, Leesburg, VA 20176 · 18+
Next Stop Comedy at Vanish Brewery in Lucketts! - Leesburg, VA Fri 11 Sep 2026, 8:00 PM — Comedy Vanish Farmwoods Brewery · 42245 Black Hops Lane, Leesburg, VA 20176
2026 Family Free Shopping Spree Sat 12 Sep 2026, 9:00 AM — Meetup Douglass Community Center · 407 East Market Street, Leesburg, VA 20176
Roper Romp Charity Pub Crawl Sat 12 Sep 2026, 2:00 PM — Meetup Downtown Leesburg (10 W Market St) · 10 W Market St, Leesburg, VA 20176 · 21+
2026 Roper Romp Charity Pub Crawl Sat 12 Sep 2026, 2:00 PM — Meetup 10 W Market St · 10 West Market Street, Leesburg, VA 20176 · 21+
Bad Animals - The Heart Tribute Sat 12 Sep 2026, 6:00 PM — Live music Tarara Winery · 13648 Tarara Lane, Leesburg, VA 20176
Live Wire: The Ultimate AC/DC Experience Sat 12 Sep 2026, 7:00 PM — Live music Tally Ho Theater · 19 W Market St, Leesburg, VA 20176 · 18+
Naghma Live Concert Virginia US Sat 12 Sep 2026, 7:00 PM — Live music 18980 Upper Belmont Pl · 18980 Upper Belmont Place, Leesburg, VA 20176
Free String Quartet Concert Sat 12 Sep 2026, 7:00 PM — Live music Holy Trinity Lutheran Church · 605 West Market Street, Leesburg, VA 20176
Mommy & Me Chocolate Sculpture Workshop Sun 13 Sep 2026, 10:00 AM — class The Conche · 1605 Village Market Boulevard Southeast, Leesburg, VA 20175
GRANDDADDY CAMP--UKULELE STYLE! Sun 13 Sep 2026, 2:00 PM — class Twice Is Nice · 305 East Market Street #S, Leesburg, VA 20176
Hammerfall w/ Evergrey, Elvenking Sun 13 Sep 2026, 6:00 PM — Live music Tally Ho Theater · 19 W Market St, Leesburg, VA 20176 · 18+
Big Band Jazz Night Tue 15 Sep 2026, 7:00 PM — Live music Leesburg Junction · 2D Loudoun Street SW, Leesburg, VA 20175
Annual Symposium: Digital Flow in Dentistry Thu 17 Sep 2026, 9:00 AM — Meetup 1500 E Market St · 1500 East Market Street, Leesburg, VA 20176
Living Lipedema: From Confusion to Clarity to Reclaiming Your Life Thu 17 Sep 2026, 5:30 PM — Support group My Wellness Physicians · 1604 Village Market Boulevard Suite 119, Leesburg, VA 20175
Crossroads Music Festival 2026 w/Sister Hazel & Lol Tolhurst from The Cure Fri 18 Sep 2026, 5:00 PM — Festival Downtown Leesburg, VA · 14 Loudoun, Leesburg, VA 20175
Emo Night featuring Emo Kids Fri 18 Sep 2026, 7:00 PM — Live music Tally Ho Theater · 19 W Market St, Leesburg, VA 20176 · 18+
Black Hoof Brewing Oktoberfest 2026 Sat 19 Sep 2026, 2:00 PM — Festival Black Hoof Brewing Company · 11 S King St, Leesburg, VA 20175 · 21+
IPT Sunset Polo Charity Series 2026 Sat 19 Sep 2026, 4:00 PM — Sports 41580 Sunday Morning Ln · 41580 Sunday Morning Lane, Leesburg, VA 20176
HIGH NOON - The East Coast's Premier Tribute to Southern Rock Sat 19 Sep 2026, 6:00 PM — Live music Tarara Winery · 13648 Tarara Lane, Leesburg, VA 20176
The Rush Experience Fri 25 Sep 2026, 7:00 PM — Live music Tally Ho Theater · 19 W Market St, Leesburg, VA 20176 · 18+
Links On the Lawn: THE GREEN CARPET AFFAIR Sat 26 Sep 2026, 1:00 PM — Meetup Stone Tower Winery · 19925 Hogback Mountain Road, Leesburg, VA 20175
The Reflex - Ultimate '80s Music Sat 26 Sep 2026, 6:00 PM — Live music Tarara Winery · 13648 Tarara Lane, Leesburg, VA 20176
Double Duran: The Ultimate Duran Duran Experience Sat 26 Sep 2026, 7:00 PM — Live music Tally Ho Theater · 19 W Market St, Leesburg, VA 20176 · 18+
Sip & Bedazzle: A Rhinestone Workshop Sun 27 Sep 2026, 1:00 PM — class Black Hoof Brewing Company · 11 South King Street, Leesburg, VA 20175
Sip, Sculpt & Savor: Fall Edition Sun 27 Sep 2026, 2:00 PM — class The Conche · 1605 Village Market Boulevard Southeast, Leesburg, VA 20175
Hopefull Collective Concert/Dinner Thu 1 Oct 2026, 6:00 PM — Live music Leesburg Junction · 2D Loudoun Street SW, Leesburg, VA 20175
Thurston Howell - A Premier Yacht Rock Spectacular Sat 3 Oct 2026, 7:00 PM — Live music Tally Ho Theater · 19 W Market St, Leesburg, VA 20176 · 18+
EnglishConnect en Leesburg Wed 7 Oct 2026, 7:00 PM — Meetup La Iglesia de Jesucristo de los Santos de los Últimos Días — Edificio de Leesburg · 801 Balls Bluff Rd, NE, Leesburg, VA 20176
Next Stop Comedy at Vanish Brewery in Lucketts! - Leesburg, VA Fri 9 Oct 2026, 8:00 PM — Comedy Vanish Farmwoods Brewery · 42245 Black Hops Lane, Leesburg, VA 20176
Pumpkin Pour Paint Party Sun 11 Oct 2026, 1:00 PM — class Casanel Vineyards & Winery · 17956 Canby Road, Leesburg, VA 20175
Paws and Paints @Vanish Farmwood Brewery Fri 16 Oct 2026, 6:30 PM — Meetup Vanish Farmwoods Brewery · 42245 Black Hops Lane, Leesburg, VA 20176
Be Kind & Rewind: Ultimate 90s Experience Sat 17 Oct 2026, 7:00 PM — Live music Tally Ho Theater · 19 W Market St, Leesburg, VA 20176 · 18+
Spooky Sweets: A Halloween Mommy & Me Cake Pop Workshop Sun 18 Oct 2026, 10:00 AM — class The Conche · 1605 Village Market Boulevard Southeast, Leesburg, VA 20175
Wednesday 13, with Dead On A Sunday and Above Snakes Tue 20 Oct 2026, 6:30 PM — Goth / darkwave Tally Ho Theater · 19 W Market St, Leesburg, VA 20176 · see tallyhotheater.com
Mamma Mania - The American Tribute to ABBA Fri 23 Oct 2026, 7:00 PM — Live music Tally Ho Theater · 19 W Market St, Leesburg, VA 20176 · $37.67-$79.38 · 18+
Chocolate Boo Bash: A Mommy & Me Sculpting Workshop Sat 24 Oct 2026, 10:00 AM — class The Conche · 1605 Village Market Boulevard Southeast, Leesburg, VA 20175
Boo’d Up: A Couples Halloween Experience Sat 24 Oct 2026, 5:00 PM — Live music Fleetwood Farm Winery · 23075 Evergreen Mills Road, Leesburg, VA 20175
Botanical Watercolor - Transparent Flowers Sun 25 Oct 2026, 2:00 PM — class Sterling Hills Farm · Loyalty Road, Leesburg, VA 20176
A Grave Misunderstanding: Murder Mystery Dinner at The Branch Thu 29 Oct 2026, 6:00 PM — Meetup The Branch · 49 Catoctin Circle Southeast, Leesburg, VA 20175
Forbidden w/ Heathen and Void Mon 2 Nov 2026, 7:00 PM — Live music Tally Ho Theater · 19 W Market St, Leesburg, VA 20176 · $34.27-$63.42 · 18+
Strategic Business Planning Retreat Thu 5 Nov 2026, 9:00 AM — class Hotel Burg · 208 South King Street, Leesburg, VA 20175
Warrior Women - Self Defense Jiu-Jitsu Thu 5 Nov 2026, 6:00 PM — class Mastery Jiu-Jitsu · 161 Fort Evans Road Northeast #suite 135, Leesburg, VA 20176
Homeschool Jiu-Jitsu Class Fri 6 Nov 2026, 10:30 AM — class 161 Fort Evans Rd NE suite 135 · 161 Fort Evans Road Northeast #suite 135, Leesburg, VA 20176
Fridays at the Spray Bar Fri 6 Nov 2026, 6:00 PM — Meetup The Global Local · 102 Loudoun Street Southwest, Leesburg, VA 20175
Gold Dust Woman: A Tribute to Stevie Nicks and Fleetwood Mac Sat 7 Nov 2026, 7:00 PM — Live music Tally Ho Theater · 19 W Market St, Leesburg, VA 20176 · $28.09-$63.42 · 18+
Discover & Celebrate Your Inner Goddess! Sat 14 Nov 2026, 10:00 AM — class The Chase Club at Hotel Burg · 208 South King Street, Leesburg, VA 20175
8th Annual Art Auction Thu 19 Nov 2026, 6:00 PM — Meetup 23075 Evergreen Mills Rd · 23075 Evergreen Mills Road, Leesburg, VA 20175
EnglishConnect en Leesburg Wed 2 Dec 2026, 7:00 PM — Meetup La Iglesia de Jesucristo de los Santos de los Últimos Días — Edificio de Leesburg · 801 Balls Bluff Rd, NE, Leesburg, VA 20176
Listings are seeded from venue and organiser calendars. See them on the map.