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Where to Watch Live Music in Hunt Country

Where to Watch Live Music in Hunt Country

Written by Kaitlin Hill | Photos courtesy of Lost Barrel Brewing

September boasts a long list of live music events that are perfect for a family outing or an intimate date night. From acoustic sessions on brewery patios to a lawn picnic set to the tune of classical music, there are plenty of opportunities to catch a concert in Hunt Country this month! 

Live Music at Lost Barrel Brewing

Running all month on Fridays, Saturdays, and Sundays, Lost Barrel Brewing in Middleburg has an impressive list of performers lined up for live music in September. Headliners include JP Jones, Crazy Jane Band, Juliet Lloyd Trio, Dennis & Brad, Summer & Eric, Thirsty Drifters, and 2MB. For lovers of classic rock like the Eagles’ “Hotel California” and “Summer Breeze” by Seals & Crofts, don’t miss Winchester band Acoustic Soul on September 15 at 5:30 p.m. Artists Shane Gamble, Steve George Band, and Just South of 7 finish out a month of wonderful live shows at a venue that has it all: delicious drinks, tasty food, and a stunning setting.

BENEFIT’s Crossroads Music Festival in Downtown Leesburg

The Crossroads Music Festival is back with musical trio SHAED. This year, the event will span two evenings, September 15 and 16, and feature a total of 35 artists to raise funds for nonprofit organizations that serve Loudoun County. SHAED will perform on Friday with special guest Ryan Wright. This performance is open to the public and will take place on the Loudoun County Courthouse lawn starting at 5 p.m. On Saturday, 12 stages will be spread across 11 different venues around Leesburg with each artist performing a 60-minute set. Passes for Saturday can be purchased in advance online for $20 or on-site for $30. The full list of bands, venues, and pass information can be found at

Weekends at The Barns at Hamilton Station Vineyards 

If you haven’t visited Hamilton Station before, September is the perfect time to do it. Each weekend the venue will host a different live music act in their picturesque vineyard setting. Enjoy a glass of wine while taking in the talents of Acoustic Moose, Liberty Street, Lenny Burridge, Jim Steele, and Sela Campbell. While most performances are free to enjoy, a few of the events will be ticketed, so make sure to check out the online events calendar. And Beatles lovers take note: Mostly Fab, a Beatles tribute band, will be there on September 29 from 7 to 9 p.m. Tickets for this concert can be booked through The Barns at Hamilton Station Vineyards’ website. 

Concerts at Quattro Goombas 

This Aldie winery and brewery will have live music on Fridays and Saturdays throughout the month of September. Local favorites like Jason Masi, Nathaniel Davis, and Gary Smallwood are among the musicians that visitors to the winery will enjoy this month. And don’t miss original tunes from Dave Mininberg on September 30 who, according to his website, loves playing here for the setting, people, and pizza. 

Middleburg Community Center Free Concert Series 

Join the Middleburg Community Center on September 15 to enjoy the musical stylings of Fountains, an alternative rock/jazz band out of Warrenton. The band shares, “We are excited to show Middleburg what we’ve been working on and new music to debut!” The concert will be held in the community center’s amphitheater where guests are invited to bring a blanket or chair and get comfortable for a night of fantastic music, food, wine, and beer! This year’s concert series is also a celebration of the amphitheater, now called the Fox Trap, which was built 75 years ago. Don’t miss this wonderful opportunity to listen to music under the stars in a historic setting!

The Souled Out Band at Music on Main 

On September 16 from 6 to 9 p.m. Main Street in Warrenton will transform into an old school block party with food trucks, a beer and wine garden, kids’ activities, and live music by The Souled Out Band as part of the Allegro Concert Series. Band members Lydell Patterson, Robbie Shiley, Graham SPICE!, Jeff Bell, and Larry Banks will rock the block with a dizzying array of styles from soul and R&B to rock and country music. The setlist could include songs from favorites like Kool & The Gang, James Brown, Four Tops, ZZ Top, Eric Clapton, The Rolling Stones, Lil Jon, Nelly, and many more. ML

For additional information on these live music events and more, visit

Published in the September 2023 issue of Middleburg Life.

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