Check out our Facebook page!

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

Cindy McConnell
at Leesburg Vintner

Zach Jones Band

Zach Jones Band
at Shoes, Cup and Cork

SHREK the Musical poster

at Sona Bank

Aaron Kunk

Aaron Kunk
at Leesburg Diner

Jill Fulton

Jill Fulton Band
at MacDowell Brew Kitchen

Fiddlin’ Dave & Morgan Morrison

Fiddlin’ Dave & Morgan Morrison
at Crooked Run

Laurie Blue
at 14 Loudoun

Nino DeBarros

Nino DeBarros
at Lou Lou Boutique

Manuel Estrada on Sax
Black Shutter Antique Center

Ellen James

Ellen James at
at Very Virginia Shop

Frayed Knots
at Kings Tavern Patio

Frank Lombardi

The Crooner Frank Lombardi
at Georgetown Café

Rosewood & Ivory

Rosewood & Ivory
at Trinity House Café 6:30-8:30

Andy Hawk and the Train Wreck Endings

Andy Hawk and his Train Wreck Endings at Kings Tavern Inside

David Davol

David Davol
at Döner Bistro

City Limits Jazz Trio (Andrew Hart Jazz Trio)

City Limits Jazz Trio
at Casa Nostra

Drawing of Gary Rudinsky (c) Tim Kozak tpkozak.deviantart.com

Gary Rudinsky at
King Street Coffee


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:

November 2,
December 7,
February 1, 2019

Events for Friday, October 5, 2018

  • 6:00-8:00 History of Cemeteries & Burials. The Clerk of the Circuit Court Historic Records Division is partnering with Thomas Balch Library, local historian Jeff Ball, and the Loudoun County Office of Mapping and Geographic Information to present an exhibition on the history of cemeteries and burial practices in Loudoun County.
    Location: 18 East Market St at the 1894 Court House
  • 6:30-8:30 Shrek, The Musical. Sona Bank is hosting the drama students from Rock Ridge High School, performing songs and skits from their upcoming performance of the Broadway musical, SHREK.
    Location: 1 E. Market St.
  • 7:00-10:00 Country Rock. MacDowell Brew Kitchen is hosting Nashville recording artist, Jill Fulton, whose fiery vocals will blow you away! Get ready for some powerhouse originals and the country, blues, Motown & rock covers that you love. She is a soulful singer/songwriter and a member of the Nashville Songwriters Association International.
    Location: 202B Harrison St.
  • 7:00-10:00 Laurie Blue. The 14 Loudoun restaurant is hosting an outdoor concert on their big back patio with rock guitarist, Laurie Mangold and her musical friends, all playing an array of classic rock songs that you can sing along to.
    Location: 14 E. Loudoun St.
  • Annie Stokes6:30-9:30 Annie! SideBar is hosting live music with acoustic singer/songwriter, Annie Stokes playing a wide array of rock, pop and folk tunes on guitar.
    Location: 24 S. King St.
  • 7:00-9:00 Harp Music. Very Virginia Shop is hosting vocalist, Ellen James on Celtic harp, performing classical music, as well as folk songs and Irish ballads. Also local artist, Caroline Milne will be showcasing her painting of South King Street. Plus they are featuring free samples of over 20 different flavors of crisp Virginia peanuts and other locally made gourmet foods.
    Location: 16 S King St.
  • 7:00-10:00 Frayed Knots. Kings Tavern and Wine Bar is holding an outdoor concert with Frayed Knots, playing a wide range of acoustic tunes from rock and folk to bluegrass and blues. They consist of members of the St. James Episcopal Church and are a popular local favorite.
    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.
  • 6:30-8:30 Sax Man. Black Shutter Antique Center is hosting saxophonist, Manuel Estrada, performing jazz, pop and rock songs from yesterday and today. He has been playing sax for the past four years and is currently a student at Tuscarora High School.
    Location: 1 E. Loudoun St.
  • 6:00-9:00 Dave Goodrum. Bike TrAle Brewery is featuring acoustic rock guitarist, David Goodrum, playing classic rock songs from yesterday and today.
    Location: 101 Loudoun St. SE
  • 6:30-8:30 Jazz Keyboardist. Lou Lou Boutique is hosting Nino DeBarros, playing jazz and contemporary songs on keyboard, backed with chill electronic music. He plays a lot of jazz standards but improvises and mixes well known songs with jazz and beats.
    Location: 9 Loudoun St. SW
  • 6:30-8:30 Aaron Kunk. The Leesburg Diner is hosting classical guitarist, Aaron Kunk, who is also a music teacher at Rock Ridge High School.
    Location: 9 S. King St.
  • 6:30-9:30 Jazz Trio. Trungo’s is is hosting a night of jazz music with the Lisa Fiorilli Trio playing raspy smooth covers of pop, rock, and jazz tunes. For those of you who think raspy smooth sounds like an implausible oxymoron, come hear how they pull it off with Lisa Fiorilli on saxophone, Patrick Fritz on guitar and Fernando Bolanos on bass.
    Location: 2 W. Loudoun St.
  • 6:30-8:30 Mayleen. Trinity House Café is hosting Mayleen preforming classical and contemporary music on her keyboard. With more than five years of experience, Mayleen has been playing piano for more than half of her life.
    Location: 101 E. Market St. (corner of Market and Church St.)
  • Caleb Nei6:00-10:00 Jazz Music. The Lightfoot Restaurant is featuring the Caleb Nei Duo with Caleb Nei on piano and Kevin Johnson on upright bass, playing an array of fabulous jazz tunes.
    Location: 11 N. King St.
  • 6:30-8:30 Zach Jones. Shoes, Cup and Cork is hosting singer/songwriter, Zach Jones on guitar, playing an array of cool songs. Zach is known as the lead singer of Never Born to Follow, a local band that recently opened for Bon Jovi.
    Location: 17 N. King St.
  • 6:30-8:30 Mrs Universe North America. Leesburg First Friday is featuring DeAnna Emborski, who is the current, Mrs Universe North America, as she will be roaming around historic downtown Leesburg to meet people and signing autographs for anyone who wants one. She is also accepting donations to benefit WAVE - Women Against Violence Everywhere - with their worldwide efforts to against domestic violence.
    Location: all around downtown
  • 7:00-10:00 Jazz Piano. Casa Nostra, downtown newest Italian restaurant, is hosting live music by the City Limits Jazz Trio, featuring locally acclaimed Andrew Hart, as the piano man.
    Location: 2 W. Market St.
  • 7:00-9:00 Crooner Tunes. Georgetown Café is hosting Frank Lombardi, of Crooners Entertainment. Frank, “The Crooner” performs in the stylings of Sinatra, Martin, Bennett, Como and many other Crooners as he is dedicated to preserving the music of the great American Standards Songbook!
    Location: 19 S. King St.
  • 6:00-9:00 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, artwork will be on display by their Artist of the Month, who is Leanne Fink for October.
    Location: 110 S. King St.
  • 6:30-8:30 Chili Cook-off with Music. Pangle and Associates is hosting a chili cook-off along with rock guitarist, Joshua Lapham, accompanied by his dad, John on the drums, playing a wide array of rock and blues tunes.
    Location: 109 S. King St.
  • 6:00-9:00 DJ ZBreezy. Bites Wine and Grilled Cheese Bar is hosting music from DJ ZBreezy, on their front porch with an extended happy hour! So grab a seat and a pitcher of Sangria and get ready for some great tunes!
    Location: 105 S. King St.
  • 6:00-1:00 Live Music. 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.
  • logo6:00-9:00 DCA. The Tryst Gallery is hosting over 30 local artists for the opening reception of their new group show, DCA. Their featured artist for the month of October, is Tryst Gallery's Jim Sisley, who will be speaking at 7 pm. Light refreshments offered.
    Location: 312 E. Market St.
  • Jan and Jeff7:00-9:00 Jan and Jeff. Designer Goldsmith is hosting the popular guitar duo, Jan & Jeff, performing from their wide repertoire of songs, from classic rock to contemporary to bluegrass and old standards.
    Location: Market Station Lower Level
  • 6:00-9:00 David Davol. Doener Bistro is hosting acoustic guitarist/singer, David Davol, highlighting the Folk-Rock style of the 60's and 70's. He also performs selections of modern country music, as well as classic rock and alternative tunes. Pick your favorite hits from his 400 song request list.
    Location: 202 Harrison St.
  • 6:00-9:00 Meet Local Authors. Books and Other Found Things host monthly "meet the author" events with local authors available to discuss and sign copies of their books. This month’s author is Steve Dressing, who wrote the book, Game Keeper.
    Location: 13 Loudoun St. SW
  • 6:00-9:00 Doris Kidder’s Art. Photoworks is featuring an exhibit entitled A Special Retrospective of Art by Doris Kidder with her unique images displayed throughout the gallery.
    Location: 2A Loudoun St. SW
  • Loudoun Street Studios6:30-8:30 Art Demo! Loudoun Street Studios is hosting an open house showcasing the art of two fabulous local painters – Holly Peterson, who paints landscapes and still life in oils, along with Libby Stevens who is in the Loudoun Sketch Club and feature Loudoun County scenery in her paintings. Light refreshments served.
    Location: 2 Loudoun St. SW (upper level).
  • 6:00-9:00 Wine and Music. The Leesburg Vintner is hosting monthly wine specials with wine by the glass. Also from 7-9pm, live music with vocalist, Cindy McConnell, performing acoustic guitar folk/rock covers.
    Location: 27 S. King St.
  • 6:00-9:00 Expo. Makersmiths is hosting an open house to showcase the wide array of things you can make at this local makerspace. You can take a tour and get involved with one of their interactive demonstrations. Check out their woodshop, metal shop, 3D printing, CAD, CNC, crafts, and ceramics studio. Makersmith is building a community of Makers by providing a facility with tools, training and other enabling resources.
    Location: 106 Royal St. SW
  • The Fine Gallery6:00-9:00 New Exhibit. The Fine Gallery is hosting an opening reception entitled 'When Data is Center' featuring 10 paintings and one video installation by Kaeley Boyle, about the changing Loudoun County environment and our relationship with the boxes that are peppering our visual landscape. An artist talk and short Q+A will start at 6:30.
    Location: 9 Royal St. SW
  • 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.
  • 6:00-9:00 Wine Tasting. 27 South Interiors is hosting wine tasting with Stone Tower Winery. Stop by their lovely home décor boutique, which features high quality home furnishings and accessories, made all around the world.
    Location: 27 S. King 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
  • 6:00-9:00 Chicago Style. Windy City Red Hots is celebrating a "Chicago Happy Hour," in downtown Leesburg with cold beers and showcasing their authentic Chicago style foods. Stop by to get a quick bite of Chicago, without traveling half way across the country.
    Location: 28 S. King St.
  • 6:00-8:00 Open House! The Sunflower Shack is featuring an old fashioned soda tasting. Bring the family out to sample over a dozen varieties of nostalgic drinks. Enjoy complimentary refreshments, while you browse an array of old fashioned candies and be sure to check out their selection of free books!
    Location: 209 Loudoun Street SE
  • 6:00-9:00 Local Cider and Art. Visit Loudoun is hosting a tasting event with Great Country Farms Cider and Doughnuts along with the Friends of Claude Moore Park photography exhibit.
    Location: Market Station - Upper Level.
  • 6:00-9:00 New Art Gallery. The Veron Ennis Artist Studio is hosting a new art exhibit entitled, Unconventional Landscapes, featuring Veron Ennis, an abstract painter and sculptor, along with guest artist, Luke Greer, a heritage photographer. Both artists draw inspiration from local landscapes and have an expressive appreciation for wide open perspectives with expansive qualities. Greer's high-contrast black and white approach emphasizes historical significance while Ennis employs sophisticated use of dramatic color and geometry in her compositions and takes it to the next level with her transformative cube sculptures. Her artwork has be exhibited in London, New York and Miami and found in private collections around the world. Visit the Studio and be first to see new works before they are shipped out to Ennis's representing galleries.
    Location: 10G S. King St. (upper level)
  • 6:00-9:00 Student Artists. The Leesburg Commission on Public Art is featuring the mixed media art work by students of art teacher W. Scott Russell at Balls Bluff Elementary School in Leesburg as their artwork will be on display through October 2018.
    Location: Town Hall (25 W. Market St – 2nd Floor Gallery)
  • 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 Moving Sale! The Jean Whisperer is hosting an open house event, featuring a moving clearance sale of their summer fashions, showcasing a wide array of jeans and other accessories such as boots, belts, scarves and fabulous jewelry.
    Location: 3 W. Loudoun St. SW

Live Music Events
Art Exhibits
Wine Tastings

... and so much more!

Leesburg Downtown Business Association
Leesburg: Discover the Charm