Upcoming live music in Loudoun County: dates, times, venues and ticket prices for this weekend and the weeks ahead, updated daily.
All Northern Virginia events · All DMV events
Wed, Oct 28, 2026 · 6:00 PM · Free · O'Malley's Pub, 45425 Holiday Drive, Sterling, VA 20166
Come for Happy Hour, stay for live music! Enjoy Live Music Wednesdays at O'Malley's featuring a rotating lineup of talented local artists performing in a relaxed, neighborhood pub atmosphere. It’s the
Thu, Oct 29, 2026 · All day · Free · Spanky's Shenanigans, 538 East Market Street, Leesburg, VA 20176
On the deck
Fri, Oct 30, 2026 · All day · Free · Trackside, 19 West Market Street, Leesburg, VA 20176
Burn the ballroomOVER 55 MILLION STREAMS AND COUNTING… BURN THE BALLROOM IS A ROCK PROJECT FOUNDED IN THE WASHINGTON DC METRO AREA, BASED BETWEEN DC AND NASHVILLE. BTB BLURS THE LINES BETWEEN ANTHEM,
Fri, Oct 30, 2026 · 6:00 PM · Free · Solace Brewing Company, 42615 Trade West Drive Suite 100, Sterling, VA 20166
Live music at Solace in Sterling every Friday night featuring local artist's. Check the website, solacebrewing.com, for a list of specific acts.
Sat, Oct 31, 2026 · All day · Free · Tally Ho Theater, 19 West Market Street, Leesburg, VA 20176
COSTUME CONTEST: Best costume wins $100 cash! Winner will be selected on stage by the band and crowd participation at intermission. Whiskey Glasses: Morgan wallen tribute Introducing Whiskey Glasses,
Details for A Haunted Honky Tonky with Whiskey Glasses (Morgan Wallen Tribute)
Sat, Oct 31, 2026 · All day · Free · Spanky's Shenanigans, 538 East Market Street, Leesburg, VA 20176
Play live on the non-smoking stage 8pm-midnight
Sat, Oct 31, 2026 · 1:00 PM · $21.05–$87.21 · Stone Bridge High School, 43100 Hay Road, Ashburn, VA 20147
Experience the Loudoun Symphony's family favorites!
Sat, Oct 31, 2026 · 1:30 PM · Free · 8 Chains North Winery, 38593 Daymont Ln, Waterford, VA 20197
Enjoy live music with David Andrew Smith . Often dubbed “Cat Stevens meets Adam Levine,” David is a Pop/Rock singer-songwriter and guitarist from the Baltimore-Washington area. He has a repertoire of
Sat, Oct 31, 2026 · 1:30 PM · Free · Fleetwood Farm Winery, 23075 Evergreen Mills Rd, Leesburg, VA 20175
Dan Barry is a singer-songwriter who blends rock, jazz, folk, and soul into a sound that’s entirely his own. His live performances guide listeners through both familiar favorites and deeper cuts, all
Sun, Nov 1, 2026 · 1:30 PM · Free · 8 Chains North Winery, 38593 Daymont Ln, Waterford, VA 20197
Enjoy live music with Gary Smallwood . Gary grew up playing the drums and bass guitar, finally switching to the guitar in high school. He is self-taught, with Hendrix, Clapton, Trower, Marino & Van Ha
Sun, Nov 1, 2026 · 1:30 PM · Free · Fleetwood Farm Winery, 23075 Evergreen Mills Rd, Leesburg, VA 20175
Scott Kurt brings a unique blend of Southern grit and Rust Belt rock to his signature country sound. Influenced by artists like Eric Church, Jon Pardi, Luke Combs, and Tom Petty, he delivers authentic
Mon, Nov 2, 2026 · 7:00 PM · Free · Heathen, 19 West Market Street, Leesburg, VA 20176
FORBIDDEN: Godfathers in the Bay Area metal scene, Forbidden have returned with their first album in 16 years to unleash 12 fierce, uncompromising, and supremely progressive songs which signal an almi
Thu, Nov 5, 2026 · 7:00 PM · Free · The Barns at Hamilton Station, 16804 Hamilton Station Road, Hamilton, VA 20158
An intimate duo performance of America's greatest singers and songwriters.
Fri, Nov 6, 2026 · 7:00 PM · Free · Tally Ho Theater, 19 West Market Street, Leesburg, VA 20176
It’s hard to imagine a band just coming into their own after 20 years of success, but that’s exactly what makes a true anomaly. Gaelic Storm, a multi-national, Celticjuggernaut grows stronger with eac
Sat, Nov 7, 2026 · 1:30 PM · Free · 8 Chains North Winery, 38593 Daymont Ln, Waterford, VA 20197
Enjoy live music with Brian Franke . Brian is an independent award-winning singer-songwriter with a popular following in Virginia. He’s a versatile musician, playing a range of Folk and Singer-songwri
Sat, Nov 7, 2026 · 1:30 PM · Free · Fleetwood Farm Winery, 23075 Evergreen Mills Rd, Leesburg, VA 20175
Garrett Mabe is a talented singer, songwriter, and performer who has been sharing his passion for music with audiences across the East Coast for over 15 years. From weddings and festivals to corporate
Sat, Nov 7, 2026 · 7:00 PM · Free · Gold Dust Woman Show, 19 West Market Street, Leesburg, VA 20176
GOLD DUST WOMAN is an 8-piece band that takes audiences in to the legendary, chart topping 4+ decades of the timeless music of Stevie Nicks’ legendary solo career, along with the Fleetwood Mac classic
Details for Gold Dust Woman: A Tribute to Stevie Nicks and Fleetwood Mac
Sat, Nov 7, 2026 · 8:00 PM · $97.88–$113.89 · Ambiance Banquet Restaurant & Event Hall, 44184 Ashbrook Marketplace Plaza, Ashburn, VA 20147
Dinner. Nostalgia. Dance floor magic. Enjoy a dinner and Sergey Shakhov’s Golden Hits concert & disco party—all included in your ticket.
Details for GOLDEN HITS — Sergey Shakhov | Dinner, Concert & Disco Party
Sun, Nov 8, 2026 · 1:30 PM · Free · 8 Chains North Winery, 38593 Daymont Ln, Waterford, VA 20197
Enjoy live music with Shane Gamble . A Maryland native, he embodies what it means to be a working musician. He attacks his guitar with passion and sings songs about the good times with a distinctly Am
Sun, Nov 8, 2026 · 1:30 PM · Free · Fleetwood Farm Winery, 23075 Evergreen Mills Rd, Leesburg, VA 20175
Join us for an afternoon of music with Dave Goodrum, a Leesburg-based solo acoustic artist performing hits from the ’70s to today. Blending rock, blues, funk, pop, and more, Dave brings a fresh mix of
Sun, Nov 8, 2026 · 4:00 PM · Free · Waterford Concert Series , Fairfax Street, Waterford, VA 20197
Mezzo Soprano - Stephanie Doche receives high praise as magnificent and brilliant for her rich coloratura, irresistible stage presence and outstanding technical and interpretive skills, “a true operat
Sun, Nov 8, 2026 · 4:00 PM · $7.18–$17.85 · Stone Bridge High School, 43100 Hay Road, Ashburn, VA 20147
Featuring music presented by LSYO's four ensembles!
Sat, Nov 14, 2026 · 1:30 PM · Free · 8 Chains North Winery, 38593 Daymont Ln, Waterford, VA 20197
Enjoy live music with Zach Jones . His acoustic sets are a unique blend of music spanning several different artists and decades. He covers the likes of Stone Temple Pilots, Neil Young, The Lumineers,
Sat, Nov 14, 2026 · 1:30 PM · Free · Fleetwood Farm Winery, 23075 Evergreen Mills Rd, Leesburg, VA 20175
Spend your afternoon unwinding with Luke Andrews, whose versatile setlist offers a little something for everyone. Enjoy a blend of country, folk, indie, Americana, blues, jazz, and soft classic rock—a
Sat, Nov 14, 2026 · 2:00 PM · Free · The Barns at Hamilton Station Vineyards, 16804 Hamilton Station Road, Hamilton, VA 20158
Find tickets for Eric Selby at The Barns at Hamilton Station Vineyards in Hamilton on 11/14/2026 at 2:00 PM
Sun, Nov 15, 2026 · 1:30 PM · Free · 8 Chains North Winery, 38593 Daymont Ln, Waterford, VA 20197
Enjoy live music with Timmie Metz from 1:30–4:30 pm. Timmie fronts the Timmie Metz Band, and plays a mix of Rock and Soul that’s sure to entertain you!
Sun, Nov 15, 2026 · 1:30 PM · Free · Fleetwood Farm Winery, 23075 Evergreen Mills Rd, Leesburg, VA 20175
Join us for an afternoon of live music with Benjamin Weimer, a talented and down-to-earth performer bringing an incredible mix of rock, pop, and country classics to life. From timeless hits by Johnny
Tue, Nov 17, 2026 · 7:00 PM · $17.85 · Leesburg Junction, 2D Loudoun Street SW, Leesburg, VA 20175
Come enjoy Big Band Night with band Swing Shift. Food & drinks available to order from Casa de Avila.
Sat, Nov 21, 2026 · 1:30 PM · Free · 8 Chains North Winery, 38593 Daymont Ln, Waterford, VA 20197
Enjoy live music with Patty Reese , a prolific Americana musician. A fan and critic favorite, Reese has been recognized by the Washington DC Area Music Association with 17 awards including Artist, Son
Sat, Nov 21, 2026 · 1:30 PM · Free · Fleetwood Farm Winery, 23075 Evergreen Mills Rd, Leesburg, VA 20175
Spend your afternoon with Ryan Sill, a talented singer-songwriter and finalist from The Voice Season 7. Known for his smooth pop vocals blended with the soulful edge of blues and rock, Ryan brings a c
Sat, Nov 21, 2026 · 2:00 PM · Free · Breaux Vineyards, 36888 Breaux Vineyards Lane, Purcellville, VA 20132
Find tickets for Melanie Pearl at Breaux Vineyards in Purcellville on 11/22/2026 at 2:00 PM
Sat, Nov 21, 2026 · 2:00 PM · Free · Two Twisted Posts Winery & Tavern, 12944 Harpers Ferry Road, Purcellville, VA 20132
Find tickets for Mo Safren at Two Twisted Posts Winery in Purcellville on 11/21/2026 at 2:00 PM
Sat, Nov 21, 2026 · 7:30 PM · $25.31 · Leesburg Junction, 2D Loudoun Street SW, Leesburg, VA 20175
Featuring saxophonists Rob Maletick, John Kocur, and Richie Conn
Details for Loudoun Jazz Society Presents: A Saxophone Summit
Sun, Nov 22, 2026 · 12:00 PM · $28.52–$172.57 · Ivy By The Lake, 46110 Lake Center Plaza, Sterling, VA 20165
Fall Soul Sessions Live band, smooth R&B, soulful vibes & great people! Nov 22, 12–4PM at Ivy by the Lake. Don’t miss this day party!
Sun, Nov 22, 2026 · 1:30 PM · Free · 8 Chains North Winery, 38593 Daymont Ln, Waterford, VA 20197
Enjoy live music with David Thong . David is a seasoned musician, performing since he was 9 years old. His versatility in the local music scene has made him a household name in the Washington, D.C. ar
Sun, Nov 22, 2026 · 1:30 PM · Free · Fleetwood Farm Winery, 23075 Evergreen Mills Rd, Leesburg, VA 20175
Join us for an afternoon of music with Shane Gamble, a Maryland native blending Country, Rock, Pop, and Americana into a sound that’s uniquely his own. With a career that includes a Top 10 single on S
Fri, Nov 27, 2026 · 6:00 PM · Free · Dirt Farm Brewing, 18701 Foggy Bottom Road, Bluemont, VA 20135
Grab a pint and join the music! Join us for a Jam Session on the last Friday of every other month! This is an open, laid-back night where local musicians and music lovers come together to share songs,
Sat, Nov 28, 2026 · 1:00 PM · Free · Creek's Edge Winery, 41255 Annas Lane, Lovettsville, VA 20180
Find tickets for Melanie Pearl at Creek's Edge Winery in Lovettsville on 11/28/2026 at 1:00 PM
Sat, Nov 28, 2026 · 1:30 PM · Free · 8 Chains North Winery, 38593 Daymont Ln, Waterford, VA 20197
Enjoy live music with Jason Teach . Jason is a singer-songwriter who has played and performed for more than 20 years. His sound has evolved over the years, yet some things have always remained true. H
Sat, Nov 28, 2026 · 1:30 PM · Free · Fleetwood Farm Winery, 23075 Evergreen Mills Rd, Leesburg, VA 20175
Spend your Sunday afternoon with the Lindsay Austin Duo, bringing their signature blend of acoustic charm and smooth harmonies to Fleetwood. Perfect for a laid-back day with great wine, their performa
Sun, Nov 29, 2026 · 1:30 PM · Free · 8 Chains North Winery, 38593 Daymont Ln, Waterford, VA 20197
Enjoy live music with Garret Mabe . With a song list of 600+ songs, Garrett performs a wide range of genres, artists, as well as your favorite tunes. Don’ miss this accomplished musician.
Sun, Nov 29, 2026 · 1:30 PM · Free · Fleetwood Farm Winery, 23075 Evergreen Mills Rd, Leesburg, VA 20175
Zach Jones is a Northern Virginia–based musician known for his versatile solo acoustic sets. His performances blend classics and modern favorites—from The Beatles and Neil Young to John Mayer, Dave Ma
Sun, Nov 29, 2026 · 2:00 PM · Free · Flying Ace Farm, 40950 Flying Ace Lane, Lovettsville, VA 20180
Find tickets for Melanie Pearl at Flying Ace Farm in Lovettsville on 11/29/2026 at 2:00 PM
Sat, Dec 5, 2026 · 1:30 PM · Free · 8 Chains North Winery, 38593 Daymont Ln, Waterford, VA 20197
Enjoy live music with Dan McGuire . Dan plays modern and classic music—hits from the 80s to today. Combining expert musicianship and incredible vocal range, each show is unique and captivating. And he
Sat, Dec 5, 2026 · 1:30 PM · Free · Fleetwood Farm Winery, 23075 Evergreen Mills Rd, Leesburg, VA 20175
Join us for an unforgettable afternoon with Laura Cashman, a powerhouse vocalist and Best of Loudoun 2024 Finalist! Known for her unmatched energy and crowd engagement, Laura brings a wide-ranging set
Sun, Dec 6, 2026 · 1:30 PM · Free · 8 Chains North Winery, 38593 Daymont Ln, Waterford, VA 20197
Enjoy live music with Chris Compton . Chris is a lifelong musician and multi-instrumentalist. He has played in ensembles ranging from choirs and Jazz combos to Reggae, Rock, Pop and Country bands. He
Fri, Dec 11, 2026 · 6:00 PM · $49.87 · YogaSix Ashburn, 44185 Ashbrook Marketplace Pl., Ashburn, VA 20147
Meditate with music by Dave Eggar is a world-renowned cellist and pianist, celebrated for Coldplay’s “Viva La Vida”.
Sat, Dec 12, 2026 · 1:30 PM · Free · 8 Chains North Winery, 38593 Daymont Ln, Waterford, VA 20197
Enjoy live music with Stanley Whitaker . Whitaker is a singer-songwriter from the Baltimore/Northern Virginia region. He’s perhaps best known for his guitar work in critically acclaimed ’70’s progress
Sat, Dec 12, 2026 · 2:00 PM · Free · Two Twisted Posts Winery, 12944 Harpers Ferry Road, Purcellville, VA 20132
We highly recommend getting a reservation for this event as the space fills up fast! Charles Washington Symphony Orchestra will fill our tasting room with the timeless sounds of Christmas classics. Co
Sat, Dec 12, 2026 · 4:00 PM · Free · The Master Singers of Virginia, 380 East Colonial Highway, Hamilton, VA 20158
Celebrate the joy of the Christmas season with the Master Singers of Virginia!
Details for Master Singers of Virginia Christmas Concert Wolcum Yole!