Weekends don’t get to have all the fun. From trivia and game nights to karaoke and pickleball, there’s plenty happening around Leesburg after the workday ends. Next time you find yourself wondering what to do on a weeknight, start here.
Monday
Chess Club at Green Tree Tavern – Whether you’re a regular player or just looking for a friendly match, pull up a chair for a game.
Trivia at Black Hoof Brewing Company – Put your knowledge to the test over a locally brewed beer.
Charity Bingo at Loudoun Kitchen & Bar – Play a few rounds of bingo while supporting a local organization.
Open Mic Night at Crooked Run Fermentation – Take the mic or grab a drink and enjoy performances from local musicians, comedians and more.
Tuesday
Line Dancing at Loudoun Kitchen & Bar – Grab your boots and hit the dance floor for an evening of line dancing.
Trivia at Green Tree Tavern – Gather your smartest friends and put all that random knowledge to good use.
$5 Movies at Phoenix Theatres – Catch a movie for just $5, leaving a little extra in the budget for popcorn.
Game Night at Dynasty Brewing Company – Grab a game, a beer and some friends for a little friendly competition.
Wednesday
Trivia at Loudoun Kitchen & Bar – Test your knowledge while enjoying a midweek night out.
All Levels Drop-In at Village Pickle – Grab a paddle and drop in anytime from 5 to 9 p.m., whether you’re experienced or still getting the hang of pickleball.
Karaoke at Green Tree Tavern – Pick your go-to song and take the stage.
Trivia at Crooked Run Fermentation – Another chance to gather your team and put your random knowledge to the test.
Thursday
Trivia at October One Vineyard – On the third Thursday of the month, pair a glass of Virginia wine with a little friendly competition.
Karaoke at Tarbender’s Lounge – Warm up those vocal cords and take the mic.
Trivia at Loudoun Kitchen & Bar – Grab your team for another chance to compete.
Jackbox Game Night at Crooked Run Fermentation – Use your phone as the controller for an evening of interactive party games.
Friday
Candle Making at The Global Local – Choose your favorite fragrances and pour your own custom-scented candle.
Live Music at Spanky’s Shenanigans – Keep the weekend soundtrack going with another spot for live music in Leesburg.
Yappy Hour at October One Vineyard – Bring your four-legged drinking buddy along on the last Friday of the month.
Live Music at Crooked Run Fermentation – Grab a beer and settle in for a Friday night performance.
Karaoke at Loudoun Kitchen & Bar – Start the weekend by taking the stage and singing your favorites.
Live Music at Green Tree Tavern – Kick back and start your weekend with live music.
Whether you’re looking for friendly competition, a creative night out, live entertainment or just an excuse to get out of the house, there’s no need to wait for Saturday. Pick a night, grab a friend and see what Leesburg has going on after 5pm.
Recurring events, dates and times are subject to change. Check directly with each business for the latest schedule before heading out.