Best Live Music at Wineries & Breweries

You don't need a festival ticket to hear live music in Loudoun — these venues run real weekly programs, from mountaintop weekend sets to Sunday-afternoon vineyard series. Days shift seasonally, so confirm the calendar before driving out.

Updated July 2026

Our take: Rankings are our editorial opinion from research and reviews — not paid placements. Policies and hours change, so confirm before visiting.

The ranking

1
Bluemont

Bear Chase Brewing Company

Live music Friday, Saturday, and Sunday on the mountaintop — the most music-per-week of any venue in the county.

2
Purcellville

Doukénie Winery

Local rock, pop, and folk acts fill the pavilion every Saturday and Sunday beside the pond.

3
Purcellville

Breaux Vineyards

Live music every Saturday and Sunday from 2–5pm across the sprawling Cajun-accented estate.

4
Leesburg

Vanish Farmwoods Brewery

Bands play every weekend at the farm brewery — Friday evening shows plus Saturday and Sunday afternoon sets.

5
Lovettsville

Flying Ace Farm

Live music Friday through Sunday at the combination farm brewery and distillery.

6
Hillsboro

Old 690 Brewing Company

Music nearly every open day — Friday evening performers plus weekend afternoon sets at the Hillsboro farm brewery.

7
Purcellville

Two Twisted Posts Winery

"Live music every weekend" is the house promise, with third-Friday evening shows layered on top.

8
Hamilton

The Barns at Hamilton Station Vineyards

Outdoor sets every Saturday and Sunday afternoon, 2–5pm, year-round at the restored 1910 dairy barn.

Keep exploring

Browse our ranked best-of lists or line up a safe, chauffeured way to tour the county.