The 5 Best Happy Hours Around Loudoun

Happy hour isn’t just about drink specials—it’s a cherished ritual that marks the shift from hustle to unwind. In Loudoun County, you’ll find plenty of local gems offering more than discounted cocktails. These spots, voted Best of Loudoun 2025, serve up everything from gourmet small plates to live music, turning a simple evening outing into a reason to celebrate midweek.

SideBar

With its moody lighting, stylish interior, and creative drink list, SideBar in downtown Leesburg elevates the happy hour experience. Guests can enjoy handcrafted cocktails and rotating specials in a space that blends historic charm with a modern edge. The bar’s upscale menu of bites also makes it ideal for those looking to linger into the evening.

Ahso

Chef-driven and flavor-forward, Ahso brings a refined touch to happy hour in Brambleton. Guests can sample inventive cocktails made with fresh, seasonal ingredients or dive into a curated selection of wines and small plates. The environment is welcoming but elevated, making it a popular choice for both casual after-work drinks and date nights.

Lost Barrel Brewing

Set on scenic grounds in Middleburg, Lost Barrel Brewing combines the best of outdoor relaxation and locally crafted beverages. While beer is the star here, their happy hour offerings also include wines, cocktails, and non-alcoholic sippers. Grab a drink and enjoy the sunset from the deck or unwind in their inviting taproom.

Parallel Wine & Whiskey Bar

Known for its extensive drink options, Parallel Wine & Whiskey Bar in Broadlands is a standout for happy hour lovers. From wine flights to whiskey pours and inventive cocktails, the drink list is broad and bold. Guests can also take advantage of the modern space and small-plate menu to craft their perfect early evening escape.

ResQ BBQ

At ResQ BBQ, happy hour comes with a smoky twist. This casual Leesburg spot offers more than just excellent barbecue—it pairs its savory eats with house cocktails and craft brews that fit the laid-back vibe. It’s a fun, no-frills option for those who want bold flavors and a cold drink after a long day.

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