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Caleb Nei

Caleb Nei Jazz Duo at Lightfoot Restaurant

Cindy McConnell

Cindy McConnell
at Leesburg Vintner

Manuel Estrada on Sax
at Very Virginia Shop

Lost Locals

Lost Locals at
MacDowell Brew Kitchen

Dance Manifesto
at 14 Loudoun Bar

Kimmy Swift

Kimmy Swift
at Leesburg Diner

David Goodrum
at SideBar

Nino DeBarros

Nino DeBarros
at Trinity House Café

Amr Mekki playing Accordion Music

Amr Mekki
at Georgetown Café

Laurie Blue
at Kings Tavern

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:

December 7,
February 1, 2019

Events for Friday, November 2, 2018

  • 6:30-8:30 Wonderland. The Old Town Grill is hosting the drama students from Heritage High School, performing songs and skits from their upcoming performance of the play Wonderland.
    Location: 15 S. King St.
  • 7:00-10:00 Dance Band. The 14 Loudoun restaurant is hosting a fun concert their big back patio with Dance Manifesto, who will lure you into dancing as they specialize in playing high energy music and take pride in performing what’s hot, along with the occasional sprinkling of classic dance songs for nostalgia. They offer incredible stage presence, vocal stylings, studio-perfect keys, and tight rhythms.
    Location: 14 E. Loudoun St.
  • 7:00-10:00 Rock & Blues. MacDowell Brew Kitchen is featuring the Lost Locals band, playing all kinds of rock, blues and funk featuring a bunch of fun local musicians!
    Location: 202-B Harrison St.
  • 7:00-10:00 Laurie Blue. The King’s Tavern and Wine Bar 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 sign along to.
    Location: 19 S. King St.
  • 6:30-9:00 Sax Man. Very Virginia Shop 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. Also they will be showcasing the artwork of Caroline Milne and her painting of South King Street. Plus you can stop by for free samples of over 20 different flavors of Virginia peanuts and other locally made gourmet foods.
    Location: 16 S King St.
  • Annie Stokes6:30-9:30 Annie Stokes. Bike TrAle Brewery is hosting live music with acoustic singer/songwriter, Annie Stokes playing a wide array of rock, pop and folk tunes on guitar.
    Location: 101 Loudoun St. SE
  • 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.
  • 6:30-9:30 Dave! SideBar is featuring acoustic rock guitarist, David Goodrum, playing classic rock songs from yesterday and today.
    Location: 24 S. 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 Jazz Keyboardist. Trinity House Café 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 beats.
    Location: 101 E. Market St. (corner of Market and Church 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 Ukulele Music. The Leesburg Diner is featuring vocalist, Kimmy Swift, on ukulele, performing an array of contemporary tunes.
    Location: 9 S. King St.
  • 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. Sometimes he will even incorporate R&B, funk, and show tunes into his playing as he usually plays over 200 shows a year.
    Location: 2B Loudoun St. SW
  • 7:00-9:00 Accordion Music. Georgetown Café is hosting Amr Mekki and his accordion, playing a variety of classical and contemporary tunes.
    Location: 19 S. King St.
  • 6:00-10:00 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 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.
  • 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, photography will be on display by their Artist of the Month, Gabe Splett.
    Location: 110 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 New Art Show. The Tryst Gallery is hosting the premier reception for their Purity & Nobility exhibit. The featured artist for the month of November is Deborah Bowe, who will be speaking about her works at 7 pm. Light refreshments offered.
    Location: 312 E. Market St.
  • The Fine Gallery6:00-9:00 Poetry Slam. The Fine Gallery is hosting its first artist dinner at 6pm followed by a poetry slam event at 7pm.
    Location: 9 Royal St. SW
  • 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 TBA.
    Location: 13 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
  • 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 Chocolate. Visit Loudoun is hosting a tasting event with chocolates from Veritas Artizen Chocolates along with hot chocolate.
    Location: Market Station – Lower 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. 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)

Live Music Events
Art Exhibits
Wine Tastings

... and so much more!

Leesburg Downtown Business Association
Leesburg: Discover the Charm