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Printable FlyerGet the one-page printable schedule to help guide you to all the events!

Little Mozart Academy
at Sona Bank

Jess Jocoy
at Trinity House Café

Princess Snow White and Pianist
at Coldwell Banker

The Cold North
at SideBar

Old Dominion Chorus

Old Dominion Chorus
at Georgetown Café

Bad Press Jazz
at Casa Nostra

Caleb Nei Jazz
at Lightfoot

Brittany Frazer
at 27 South Interiors

David Goodrum
at Bike TrAle Brewing

Ellen James

Ellen James at
Very Virginia Shop

Crossing Elden
at Misguided Angels

Manuel Estrada on Sax

Larisa and Chris Mangione

Chris Mangione
at Leesburg Diner

Acoustic Autumn
at King’s Tavern

King Street Band
at Wild Hare Cider Cabin

Soul Benders Jazz Trio
at TarBender’s Lounge

Joshua Lapham
at Designer Goldsmith


Different performances and special events every month!

Stroll around historic downtown Leesburg on the First Friday of each month (except January), to enjoy numerous live music performances throughout the town, art exhibits, wine tastings, lectures, signings, and so much more!

Over 45 specialty shops, art galleries, antique shops and restaurants are open until 9pm or later,
many offering free refreshments and/or special sales.

Upcoming First Friday dates for your calendar:

Nov 1
Dec 6
Feb 7, 2020
Mar 6

Events for Friday, October 4, 2019


    • 6:30-9:30 Gary Smallwood. Trungo’s is featuring locally acclaimed, singer/guitarist, Gary Smallwood playing an array of classic rock, country rock, and soulful blues and sometimes he even mixes in some funk or show tunes for fun.
      Location: 2B Loudoun St. SW
    • 6:30-9:30 David Goodrum. Bike TrAle Brewery is hosting live music with acoustic rock guitarist, David Goodrum, playing classic rock tunes from yesterday and today.
      Location: 101 Loudoun St. SE
    • 6:30-8:30 Sidewalk Sale. Lou Lou Boutique is participating in Downtown’s Sidewalk Sale on Friday night and also on Saturday, so stop by to check out all their great fashion deals!
      Location: 9 Loudoun St. SW
    • 6:30-8:30 New Art Show.Loudoun Street Studios Loudoun Street Studios is featuring their newest resident artist, Bethany Widom, along with new artwork by Libby Stevens and Carol Buswell. Stop by to check out all the cool artwork by these very talented local artists and learn about upcoming classes and workshops. Light refreshments served.
      Location: 2A Loudoun St. SW (upper level).
    • 6:00-8:00 History Open House. The Loudoun Museum is featuring history exhibits, showcasing a variety of artifacts from Loudoun County's past centuries. Stop by to check out their newest history exhibits to explore and learn a little about your County’s past.
      Location: 16 Loudoun St. SW
    • 6:00-9:00 Book Signing. Books and Other Found Things host monthly "meet the author" events with local authors to discuss and sign copies of their books. This month’s author will be Gbenga Ogunjimi and his book entitled Borderless Voice: The Power of Telling Your Story and Defining you Identity.
      Location: 13 Loudoun St. SW
    • 6:00-9:00 Photography Show. Photoworks is featuring a travel photography show as KD Kidder will share photos and stories of her exciting visit to the most amazing health clinic in the world outside Bangalore India with an array of her images displayed throughout the gallery. Plus enjoy award winning wines from Fabbioli Cellars.
      Location: 2A Loudoun St. SW
    • logo6:00-9:00 Art and Music. Art Sweet Art is hosting an art show entitled The Influencers: Color and Texture Exhibit, along with music by Fourte Cello Choir and the Suite Four String Quartet. Also, Belgian Chocolates.
      Location: 2B Loudoun St. SW
    • 6:00-9:00 Trunk Show. Madisonbelle is hosting a trunk show featuring Rebel Designs and Bed Stu Bags. Also free blowouts from Modern Concepts Salon by appointment from 3pm-8pm. Contact shelley@madisonbelle.com to reserve.
      Location: 5 W. Loudoun St.
    • 6:00-8:00 Acoustic Night. Balls of Glory is hosting a live acoustic music with the musician’s name to be announced. They are experts in all things meatballs, so stop by to welcome this fun new eatery to historic downtown Leesburg.
      Location: 15 E. Loudoun St.
    • 7:00-10:00 Blues & Rock. The 14 Loudoun bar and restaurant is featuring an outdoor concert by the popular band, Something’s Brewing, playing everything from classic rock, acoustic and electric rock/pop to folk, old and new.
      Location: 14 Loudoun St. SE
    • 6:00-9:00 Art Open House. Medlin Art Gallery is hosting an Art Open House, showcasing a large selection of antique prints, maps and original artwork from such nationally-known artists as Mort Kunstler, Mary Hope Worley, Paul Landry, John Paul Strain and P. Buckley Moss. Light refreshments served.
      Location: 2 E. Loudoun St.
    • 6:00-8:30 Vintage Music. Dig! Records & Vintage is hosting an open house featuring his used LP's, 45's, vintage clothing and a selection of turntables, receivers and audio gear. They specialize in PUNK, 60's Garage, Psych, Soul/funk, Jazz, Alternative, Hip-Hop and of course, Rock-n-Roll. Get on down to this awesome shop to check out the tons of 45's from the 50's, 60's, and 70's, as they buy, sell and trade 7-inch, 10-inch, 12-inch, and Cassette Tapes.
      Location: 212C Loudoun St. SE

    • 6:30-8:30 Teen Rocker. Designer Goldsmith is hosting rock guitarist, Joshua Lapham, accompanied by his dad, John on the drums, playing a wide array of rock and blues tunes.
      Location: Market Station –Lower Level.
    • 7:00-10:00 Live Music and Art. Crooked Run Brewing is featuring the group, Acid Mt. Raven Rock, playing all kinds of experimental music. They are also hosting an art exhibit by Amanda Cioffi.
      Location: Market Station Lower Level.
    • 7:00-10:00 Rock Music. The Wild Hare Hard Cider Cabin is featuring he rock band, King Street, comprised of local teenagers, playing a variety of cool rock-n-roll tunes.
      Location: Market Station – Lower Level
    • 5:00-9:00 Off The Record. MacDowell Brew Kitchen is hosting an outdoor concert with the OTR Band ("Off The Record")! The band performs a diverse selection of popular covers from the '80s, '90s, and 2000s, and other classic rock and R&B "deep cuts" from Adele to Zeppelin. The group prides itself on well-rehearsed, complex musicianship and even features a high-octane horn section.
      Location: 202-B Harrison St.
    • 6:00-7:00 Free Yoga Lesson. Flow Yoga is offering a FREE fun-filled yoga practice, which is open to all experience levels.
      Location: Market Station - 3rd floor.
    • 6:00-9:00 Fall Event. Visit Loudoun is hosting a fall event with cider tasting from Great Country Farms, along with samples of their cider doughnuts. Light refreshments offered.
      Location: Market Station – Lower Level.

    • 6:30-10:00 Stroll the Street. We are hosting an event called Stroll the Street, as the part of South King Street between Loudoun and Market will be closed to vehicular traffic, so people have more space to stroll around. There will not be any vendors, booths or sales going on in the closed area. Aside from large groups and families with children being able to walk safely on this one block of King Street, the rest of Leesburg First Friday is as usual.
      Location: South King Street between Loudoun and Market
    • 6:00-9:00 Rock the Pink. A Wedding Loft is hosting Tru Colour Studios presenting ROCK THE PINK in honor of October being Breast Cancer Awareness month. Show your support by rocking a pink hair extension all month with $10 cash equaling one hair extension which also equals so much good! Every dollar donated will go directly towards the incredible and local Step Sister organization.
      Location: 11 S. King St.
    • 6:30-8:30 Harp Music. Very Virginia Shop is featuring vocalist, Ellen James on Celtic harp, performing classical music, as well as folk songs and Irish ballads. You can also taste free samples of over 20 different flavors of Virginia peanuts and other locally made gourmet foods.
      Location: 16 S King St.
    • 6:30-8:30 Orchestra Music. Sona Bank is hosting The Little Mozart Academy, under the direction of Gabriela Bohnett, will be performing a selection of light classical music. Good for all ages!
      Location: 1 E. Market St.
    • 6:30-9:30 Rock Tunes. SideBar is hosting The Cold North, a father and daughter rock duo, playing a variety of songs on banjo, guitar, and ukulele.
      Location: 24 S. King St.
    • 7:00-10:00 Rock Band. The King's Tavern and Wine Bar is hosting a fun concert on their back patio with Acoustic Autumn, a rock band featuring some long time musicians playing a wide range of awesome tunes from rock and folk to bluegrass and blues.
      Location: 19 S. King St. back patio
    • Drawing of Gary Rudinsky (c) Tim Kozak tpkozak.deviantart.com6:00-9:00 Music and Art. King Street Coffee is featuring live music by Gary Rudinsky, along with many talented students from the music department of Loudoun County High School. Plus, an abstract mixed media art exhibit will be on display by their Artists of the Month, Nina Harrast and Sean Patten.
      Location: 110 S. King St.
    • 6:00-9:00 Yum! Gruto’s Ice Cream Shop is featuring their yummy soft serve ice cream, which they make locally with love. Stop by to see how this little parlor is all about having a good time while enjoying delicious and affordable ice cream!
      Location: 107 S, King St.
    • DJ ZBreezy6:00-9:00 DJ ZBreezy. Bites Wine and Grilled Cheese Bar is hosting music from DJ ZBreezy, on their front porch with an extended happy hour!
      Location: 105 S. King St.
    • 6:00-8:00 Jazzy Tunes. The Leesburg Diner is hosting live music with Chris Mangione on guitar, playing a wide array of jazzy music.
      Location: 9 S. King St.
    • 6:00-9:00 Adopt a Pet. Be Beauty is hosting a kitten adoption event with Pet Connect Rescue. If you want a cute cat and snuggle buddy, come meet your new best friend!
      Location: 13 S. King St.
    • 6:30-8:30 Snow White. Coldwell Banker is hosting a meet and greet event with Princess Snow White. Stop by to get your photo taken with this lovely princess before she falls asleep! Also live music will be provided by pianist, Mayleen Hyett.
      Location: 25 S. King St.
    • 6:30-8:30 Acoustic Duo. Misguided Angels is hosting Crossing Elden, an acoustic duo from Herndon with Mike Betti on guitar and Lisa Olsen on baritone ukulele, playing stripped down rock and folk songs from the 60s through today.
      Location: 14 S. King St.
    • 6:30-8:30 Sax Music. Senor Ramon is hosting saxophonist, Manuel Estrada, a talented high schooler, performing a wide array of jazz, pop and rock tunes from yesterday and today.
      Location: 38 S. King St.
    • 6:0-9:00 Sidewalk Sale. The Lucky Knot, an ultimate preppy store with a nautical flair, is taking part in the Annual Downtown Sidewalk Sale on Friday and Saturday this weekend. Stop by to check out all their cool and hip fashion items!
      Location: 9 N. King St
    • 6:00-9:00 Music and Wine. The Brick and Mortar Store is hosting live piano music by students from The Catoctin School of Music, along with wine tasting with October One Vineyard. Stop by to check out Leesburg’s new shop on the corner.
      Location: 34 S. King St.
    • Kelsan at piano5:30-9:00 Lots of Music. Georgetown Café is hosting pianist, Kelsan Giamporcaro, playing an array of ragtime and jazz piano tunes from 5:30-7:00pm. Afterward, they are hosting the Old Dominion Chorus, singing a variety of barber shop quartet songs in perfect harmony.
      Location: 21 S. King St.
    • 6:00-9:00 Soda Pop. The Sunflower Shack, in their new location, is featuring an old fashioned soda Tasting. Bring the family out to sample over a dozen varieties of nostalgic crème sodas, root beers and sarsaparillas!
      Location: 36 S. King St.
    • Andy Hawk and the Train Wreck Endings6:00-1:00 Andy Hawk. King's Tavern and Wine Bar is hosting locally acclaimed Andy Hawk and his Train Wreck Endings band from 6-8:30, consisting of several local music legends. Afterward, from 9-1am, it's open mike night featuring a wide array of musicians.
      Location: 19 S. King St.
    • 6:00-9:00 Free Chair Massages. The Leesburg Spa, a brand new massage salon right in the heart of downtown, is hosting an open house event with free chair massages.
      Location: 10 S. King St. Upper Level.
    • 9:00-12:00 Soul Music. The Tarbenders Lounge is hosting their house band, The Soul Benders Jazz Trio, playing an array of jams from Blues, Funk and of course, Jazz. Stop by so you can dance the night away.
      Location: 10 S. King St.
    • Cindy McConnell6:00-9:00 Wine and Music. The Leesburg Vintner is hosting monthly wine specials with wine by the glass. Also from 7-9pm, they will have live music with vocalist, Cindy McConnell, performing acoustic guitar folk/rock covers.
      Location: 27 S. King St.
    • 6:00-9:00 Wine & Music. 27 South Interiors is hosting wine tasting with Stone Tower Winery and live music with acoustic guitarist, Brittany Frazer, singing contemporary pop and rock songs. Also stop by to get your face painted by Enchanted Faces.
      Location: 27 S. King St.

    • 6:30-8:30 Live Music. Trinity House Café is hosting Nashville-based Singer/Guitarist, Jess Jocoy, playing some great tunes to keep the night hopping!
      Location: 101 E. Market St. (corner of Market and Church St.)
    • logo6:00-9:00 Two Art Exhibits. The Tryst Gallery is hosting the opening of two new shows: The Pirate Rock Exhibition and American Landscape, which features the amazing paintings of the late Jack Lancto. Stop by to check out all the cool artwork by over 40 local artists! Light refreshments.
      Location: 312 E. Market St.
    • 7:00-10:00 Jazz Piano. Casa Nostra, downtown newest Italian restaurant, is hosting live music by the Bad Press band, featuring some great jazz tunes and R&B music.
      Location: 2 W. Market St.

    • The Fine Gallery6:00-9:00 Art Open House. The Fine Gallery is hosting an open house event featuring works from local artists. This gallery is equal parts contemporary art gallery and educational art provider, focusing on an immersive art learning experience.
      Location: 9 Royal St. SW

    • 6:00-9:00 CBD Shop. The District Hemp Boutique is hosting an open house to showcase their new location in downtown Leesburg. They are the first hemp-based CBD store in the area and have a wide array of hemp products with naturally occurring cannabinoids, ranging from oils to hemp-infused dog treat. Stop by to check out Leesburg’s new shop and enjoy some light refreshments.
      Location: 19 Wirt St.

Live Music Events
Art Exhibits
Wine Tastings

... and so much more!

Leesburg Downtown Business Association
Leesburg: Discover the Charm