Middleburg Live Music Events

Live Music Happening Next in Middleburg, VA

Lost Barrel Brewing Oktoberfest 2025

 Lost Barrel Brewing 27 Sep 2025
MUSIC USD 36 TO 42

Live Music by Part Of It All at Lost Barrel Brewing

 Lost Barrel Brewing 29 Aug 2025
MUSIC

Live Music by Scott Kurt at Lost Barrel Brewing

 Lost Barrel Brewing 31 Aug 2025
MUSIC FREE

First Friday at the Manor House

 Greenhill Winery & Vineyards 5 Sep 2025
FIRST-FRIDAY

Live Music by Steve Boyd & Friends at Lost Barrel Brewing

 Lost Barrel Brewing 27 Sep 2025
MUSIC

Labor Day Margaritaville Bash

 Lost Barrel Brewing 1 Sep 2025
ENTERTAINMENT FREE

Live Music & Cousins Maine Lobster Food Truck

 495 E. Washington Street, Middleburg, VA, United States, Virginia 20117 7 Sep 2025
MUSIC

Live Music by Bill Bowman at Lost Barrel Brewing

 Lost Barrel Brewing 14 Sep 2025
MUSIC

Live Music by Scott Kurt at Lost Barrel Brewing

 Lost Barrel Brewing 12 Sep 2025
MUSIC

Melanie Pearl @ Chrysalis Vineyards

 Chrysalis Vineyards 11 Oct 2025
MUSIC

Live Music by Steve Boyd & Friends at Lost Barrel Brewing

 Lost Barrel Brewing 30 Aug 2025
MUSIC FREE

Melanie Pearl @ Chrysalis Vineyards

 Chrysalis Vineyards 30 Aug 2025
MUSIC

Caleb Nei @ Chrysalis Vineyards

 Chrysalis Vineyards 6 Sep 2025
MUSIC

Live Music by Brett Baboorian at Lost Barrel Brewing

 Lost Barrel Brewing 26 Sep 2025
MUSIC

Live Music by Scott Kurt at Lost Barrel Brewing

 Lost Barrel Brewing 20 Sep 2025
MUSIC

Live Music by Shelly & the Mudcats at Lost Barrel Brewing

 Lost Barrel Brewing 13 Sep 2025
MUSIC

Melanie Pearl @ Chrysalis Vineyards

 Chrysalis Vineyards 13 Sep 2025
MUSIC

Live Music by Sharif at Lost Barrel Brewing

 Lost Barrel Brewing 7 Sep 2025
MUSIC

Acoustic Soul at Lost Barrel Brewing

 Lost Barrel Brewing 12 Oct 2025
MUSIC

Out West Fest at Lost Barrel Brewing

 Lost Barrel Brewing 8 Nov 2025
FESTIVALS FREE

Live Music by Steve Boyd & Friends at Lost Barrel Brewing

 Lost Barrel Brewing 27 Sep 2025
MUSIC FREE

Live Music at the Barn: Bill Bowman & Greg Ryman

 495 E. Washington Street, Middleburg, VA, United States, Virginia 20117 31 Aug 2025
MUSIC

Live Music by The Coozies (Playing Jimmy Buffett) at Lost Barrel Brewing

 Lost Barrel Brewing 1 Sep 2025
MUSIC

Live Music by Elle & Ron at Lost Barrel Brewing

 Lost Barrel Brewing 21 Sep 2025
MUSIC

Live Music by Bill Bowman at Lost Barrel Brewing

 Lost Barrel Brewing 14 Sep 2025
MUSIC FREE

Virginia Fall Races After Party

 Lost Barrel Brewing 11 Oct 2025
SPORTS

5th Annual Sunset in the Field

 Farmer's Delight 19 Oct 2025
ENTERTAINMENT

LBB Annual Dog Halloween Costume Contest & Party at Lost Barrel Brewing

 Lost Barrel Brewing 26 Oct 2025
DOG FREE

Joe Martin at Chrysalis Vineyards

 Chrysalis Vineyards 4 Oct 2025
MUSIC