Crooked Run Fermentation keeps Loudoun interesting with creative lagers, IPAs, coolship sours, plus natural wines, ciders, and seltzers.…
22455 Davis Dr #120 (Sterling)
“Crooked Run Fermentation keeps Loudoun interesting with creative lagers, IPAs, coolship sours, plus natural wines, ciders, and seltzers. Swing by Sterling for NY style pizza, tacos, brunch, and cocktails, or pop into the original Leesburg spot, then check their weekly events if you like a good excuse to linger.”
From the Loudoun County newsletter, September 15, 2026
When your group wants an easygoing spot with premium hookah and exceptional flavor, Qulis Lounge keeps the vibes relaxed without skimping…
45630 Falke Plaza Unit 110 (Sterling)
“When your group wants an easygoing spot with premium hookah and exceptional flavor, Qulis Lounge keeps the vibes relaxed without skimping on quality. Perfect for unhurried catchups, evening decompression, and the simple pleasure of a well-packed bowl, plus you can book a table so everyone lands a seat.”
From the Loudoun County newsletter, September 18, 2026
Bleu Frog Vineyards pours easygoing Virginia wines with weekend live music, a laid back vibe, and bites that go beyond basic tasting-room…
16413 James Monroe Hwy (Leesburg) · ✓ checked Jul 31
“Bleu Frog Vineyards pours easygoing Virginia wines with weekend live music, a laid back vibe, and bites that go beyond basic tasting-room fare... think hot pretzels, charcuterie, sandwiches, even macarons. Perfect for a low-stress hang with friends or a small celebration when you want something simple and good.”
From the Loudoun County newsletter, September 9, 2026
Craving a spot that feels like Leesburg in all the best ways? Leesburg Public House serves seasonal snacks and refreshing beverages, with a…
962 Edwards Ferry Rd NE (Leesburg)
“Craving a spot that feels like Leesburg in all the best ways? Leesburg Public House serves seasonal snacks and refreshing beverages, with a welcoming, community-first vibe that makes dinner plans effortless and catch-ups stretch a little longer than planned.”
From the Loudoun County newsletter, September 20, 2026
October One Vineyard Wine Tasting Shop pours estate-grown Loudoun wines from their Bluemont vineyard in a relaxed Downtown Leesburg spot,…
7 Loudoun St SW (Leesburg)
“October One Vineyard Wine Tasting Shop pours estate-grown Loudoun wines from their Bluemont vineyard in a relaxed Downtown Leesburg spot, plus a curated lineup of other Virginia bottles. Swing by for trivia, live music, or Yappy Hour and find a new favorite to share.”
From the Loudoun County newsletter, August 23, 2026
Whether you're in the mood to linger over a thoughtfully curated European pour or build a shareable spread from small plates that punch…
108 South St SE Ste 101 (Leesburg)
“Whether you're in the mood to linger over a thoughtfully curated European pour or build a shareable spread from small plates that punch above their size, Gvino Wine Bar nails the cozy, rustic-meets-modern vibe. Watch for wine tastings and live music, then discover a new favorite this week.”
From the Loudoun County newsletter, August 30, 2026
Make this week feel extra adult at EagleTree Restaurant & Winery, where estate-grown wines are made on-site and the kitchen turns out…
15100 Harrison Hill Ln (Leesburg)
“Make this week feel extra adult at EagleTree Restaurant & Winery, where estate-grown wines are made on-site and the kitchen turns out seasonal, handcrafted plates built to pair perfectly. Not in a wine mood? There’s also a full craft beer lineup and rotating cocktail specials.”
From the Loudoun County newsletter, August 19, 2026
Loudoun Cider House is all about handcrafted, small-batch hard apple ciders, distinctly Virginia, whether you’re into still or sparkling,…
43376 Spinks Ferry Rd (Leesburg)
“Loudoun Cider House is all about handcrafted, small-batch hard apple ciders, distinctly Virginia, whether you’re into still or sparkling, single‑varietal or a custom blend. Easygoing, full of personality, built for relaxed hangs... the sort of pour that makes you stay for one more glass.”
From the Loudoun County newsletter, September 13, 2026
Small, unapologetic, and very serious about flavor, Night Shift Cocktails shakes up inventive sips like the smoky, spicy Driving Crooner,…
28 S King St (Leesburg)
“Small, unapologetic, and very serious about flavor, Night Shift Cocktails shakes up inventive sips like the smoky, spicy Driving Crooner, Baby! and a silky What's The Tea?. Feeling indecisive?”
From the Loudoun County newsletter, August 20, 2026
Pull up to Mt. Defiance Cidery & Distillery in Middleburg for crisp, Virginia-made ciders, small-batch gin, bourbon, and their absinthe,…
495 E Washington St (Middleburg)
“Pull up to Mt. Defiance Cidery & Distillery in Middleburg for crisp, Virginia-made ciders, small-batch gin, bourbon, and their absinthe, all shaken into seasonal cocktails or poured in tasting flights. It’s the kind of modern barn-loft hang you’ll accidentally turn into a whole afternoon this week.”
From the Loudoun County newsletter, September 22, 2026
When you want a no-fuss night with solid wines and hometown talent, King's Tavern & Wine Bar keeps the vibe easy. Check their entertainment…
19 S King St Ste b (Leesburg)
“When you want a no-fuss night with solid wines and hometown talent, King's Tavern & Wine Bar keeps the vibe easy. Check their entertainment lineup for local artists or jump into the weekly open mic, stage fright optional... perfect midweek reset with friends.”
From the Loudoun County newsletter, August 26, 2026
Green Tree Tavern brings an 18th-century Leesburg vibe with a recent glow-up, 16 taps of craft beer, and cocktails that don’t phone it in.…
15 S King St (Leesburg)
“Green Tree Tavern brings an 18th-century Leesburg vibe with a recent glow-up, 16 taps of craft beer, and cocktails that don’t phone it in. Chef Peter Ferdinand’s gastro pub menu leans local, and with eleven TVs plus Monday Chess Club and Trivia Tuesday, it’s prime for this week’s meetups.”
From the Loudoun County newsletter, August 25, 2026
Need a little breeze with your beverage? The Crow's Nest is the downtown rooftop bar locals hit for orange crushes, rum runners, and cold…
7 W Market St Unit 400 (Leesburg) · ✓ checked Aug 27
“Need a little breeze with your beverage? The Crow's Nest is the downtown rooftop bar locals hit for orange crushes, rum runners, and cold beers while watching downtown buzz below. It’s relaxed, neighborly, and just high enough to feel like you found a tiny secret.”
From the Loudoun County newsletter, September 1, 2026
Gold Cup Wine Bar is your easy win this week after a Loudoun kind of day, pouring standout Virginia wines alongside a menu that actually…
500 N Pendleton St (Middleburg)
“Gold Cup Wine Bar is your easy win this week after a Loudoun kind of day, pouring standout Virginia wines alongside a menu that actually tempts you to linger.”
From the Loudoun County newsletter, September 10, 2026
Tally Ho Theater is a Depression-era movie palace turned live music home base, an art deco treasure with real character. The lineup swings…
19 W Market St (Leesburg)
“Tally Ho Theater is a Depression-era movie palace turned live music home base, an art deco treasure with real character. The lineup swings from metal and tribute blowouts to Celtic and country and even comedy, so pick a show this week and make it a Leesburg night.”
From the Loudoun County newsletter, August 21, 2026
Spanky's Shenanigans is the neighborhood Irish pub with a spacious deck, breakfast, and bar bites made for pint pairing. Voted Loudoun's…
538 E Market St (Leesburg) · ✓ checked Aug 27
“Spanky's Shenanigans is the neighborhood Irish pub with a spacious deck, breakfast, and bar bites made for pint pairing. Voted Loudoun's Best, they keep the live music calendar stacked with local bands, plus you can order delivery or takeout when a couch concert sounds like the move.”
From the Loudoun County newsletter, September 2, 2026
