The best bars & nightlife in Leonardtown

4 bars & nightlife we’ve checked and stand behind — with the story on each one. Not a ranking; a record.

Browse another shelf: all of Leonardtown’s best · Restaurants · Beauty · Entertainment · Home & Garden · Shopping · Bakeries & Sweets · Antiques, Thrift, & Vintage · Cafes · Health & Wellness · Arts & Culture · Hobbies, Books, & Crafts · Pets

Pinned in Leonardtown today

This spot is open today.

Two pinned places a day in Leonardtown — $10 here, $25 adds the newsletter. List your business →

Paid placements are always marked.

Nightlife · 4 places · showing the latest additions first

Brüdergarten (Brü)

Nightlife

Brüdergarten (Brü) is a local beer garden for easygoing hangs, crisp pours, and the kind of neighborhood energy that makes a quick stop…

22725 Duke St

“” Check their site for the latest menu and events, then rally your crew for a relaxed evening.”

From the Leonardtown newsletter, September 26, 2026

Website ↗

Port of Leonardtown Winery

Nightlife

Escape the everyday with Port of Leonardtown Winery’s award-winning wines, seasonal wine slushies, and sangria, plus live music that makes…

23190 Newtowne Neck Rd

“Escape the everyday with Port of Leonardtown Winery’s award-winning wines, seasonal wine slushies, and sangria, plus live music that makes it easy to linger. It’s a laid-back, friends-and-family kind of spot where a quick tasting somehow becomes the highlight of your week.”

From the Leonardtown newsletter, September 21, 2026

Website ↗

Pasha Lounge

Nightlife

Pasha Lounge is the low-key, close-to-home move when you just want to relax and let the flavorful shisha do the talking. Easy vibes,…

3242 Old Washington Rd (Waldorf)

“Pasha Lounge is the low-key, close-to-home move when you just want to relax and let the flavorful shisha do the talking. Easy vibes, flavorful shisha, and a space made for catching up with friends... consider this your cue to swap group chat chaos for actual hangout time.”

From the Waldorf newsletter, September 23, 2026

Website ↗

The Remedy 20601

Nightlife

The Remedy 20601 is Waldorf's go-to dive for cold drinks, hot wings, a couple racks of pool, and live music. When you want good trouble…

3090 Old Washington Rd (Waldorf)

“The Remedy 20601 is Waldorf's go-to dive for cold drinks, hot wings, a couple racks of pool, and live music. When you want good trouble with great company, this is the low-key hang where neighbors actually talk, sing along, and order that second basket without judgment.”

From the Waldorf newsletter, September 17, 2026

Website ↗

Listed here?

You’ve earned the mark — get the BaseLocal’s Best badge for your site →. Want in? List your business →