Hoping to follow on the success of its inaugural August event, Stroll the Streets for First Friday will be back this evening as downtown Leesburg celebrates First Friday.

         27 South owner Nick McCarter, the event organizer, said feedback from the Aug.2 event which, for the first time, closed the block of King Street between Market and Loudoun streets during the First Friday festivities, was overwhelmingly positive. 

         “Obviously this is something we don’t want to stop,” he said. “It was an overwhelming success.”

         McCarter said downtown visitors to Stroll the Streets enjoyed the additional pedestrian space, especially for families with young children and strollers. And downtown businesses, even those who outside of the footprint of the event, reported some of their best sales during any First Friday. Some restaurants even had hours-long waits. The weather could not have been better either, McCarter acknowledged.

         The Town Council recently gave its OK for continuing the Stroll the Street event during First Fridays; however, the town is not footing the bill for the street closure. McCarter said that, outside of the initial almost $1,000 application fee, last month’s event cost him into the thousands of dollars by the time the cost of insurance and other line items were added up. As he looks to expand the event in the coming months, the costs will only increase, he said.

         McCarter is emphatic that he does not want Stroll the Streets to be a Nick McCarter production. To that end, he is trying to further involve the community and businesses. The first step towards that was creating a Facebook page, Leesburg Stroll the Streets, where he garnered much of the feedback that will shape this and future Stroll the Street events, he said. He is also looking to turn the reins of the event over to the Leesburg Downtown Business Association.

         “I’ll be taking on a leadership role in that organization to reinvigorate it, get businesses involved, and that will be the host of Stroll the Streets for First Friday moving forward,” he said. “The community can donate money to the organization which will then fund things like this.Businesses can become members or donate money to the organization.”

         McCarter said he had many people reach out to donate money to keep the event going, but there was nowhere to put the funds. Putting it under the auspices of the LDBA will solve that problem, he said.

         September’s event will see the addition of many kid-friendly activities, with a face painter, balloon artist, and sidewalk chalk scheduled during the early hours of the 6:30-10 p.m. event. 

Going forward, McCarter is looking to secure the ABC license to allow consumption of alcohol on the closed-off street, as well as expand the overall footprint of Stroll the Streets to other parts of the downtown. He emphasizes that Stroll the Streets is not intended to mirror a downtown festival with booths and vendors on the streets. Rather, it’s an event meant to showcase the downtown area and its shops and restaurants, and encourage visitors to patronize the brick and mortar shops.

Stroll the Streets is a work in progress, McCarter said, and the public should expect more each month. He hopes to have the ABC license in place soon, although it will not be ready for the September event, to add the outdoor alcohol consumption component to it, as well as adding more adult-friendly activities to supplement the offerings for children. Tables and chairs will also be rented in future months to allow for a seating option other than the sidewalk curb, he said.

“Every month I want this to get better,” McCarter said.

The Sept. 6 Stroll the Streets for First Friday event will run from 6:30-10 p.m. when the King Street block will be closed to traffic. More information on First Friday activities can be found at leesburgfirstfriday.com

Events for Friday, Sept. 6

Events for Friday, Sept. 6


Jazz Trio. Trungo’s 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.6:30-9:30 p.m.

Location: 2 W. Loudoun St.

Family Duo. Bike TrAle Brewery is hosting The Cold North, a father and daughter rock duo, playing a variety of songs on banjo, guitar, and ukulele. 6:30-9:30 p.m.

Location: 101 Loudoun St. SE

Ragtime. Lou Lou Boutique is hosting pianist, Kelsan Giamporcaro, playing an array of ragtime and jazz piano tunes. As a talented student at Simpson Middle School, he has been playing piano for over five years.6:30-8:30 p.m.

Location: 9 Loudoun St. SW

New Art Show. 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. 6:30-8:30 p.m.

Location: 2A Loudoun St. SW (upper level).

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. 6-8 p.m.

Location: 16 Loudoun St. SW

Local Potters. Resourceful Woman is hosting the Leesburg Vintage Potters which is made up of a talented group of senior citizens from the Leesburg Senior Center, that hand-build and hand-paint beautiful pottery items. These unique items are reasonably priced and make great gifts for all occasions. As a non-profit group, all proceeds benefit the Senior Center ceramics studio. 6-9 p.m.

Location: 11-A Loudoun St. SW

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 Robert Scott and his epic teen adventure “Gods Rough Drafts.” 6-9 p.m.

Location: 13 Loudoun St. SW

Photography Show. Photoworks is featuring a fun photography exhibit with a wide array of unique images displayed throughout the gallery.6-9 p.m.

Location: 2A Loudoun St. SW

Art and Music. Art Sweet Art is hosting an art show entitled The Influencers: Color and Texture Exhibit with live music by classical guitarist, Aidan Pershong, along with Belgian Chocolates.6-9 p.m.

Location: 2B Loudoun St. SW

Wine Tasting. Madisonbelle is hosting a wine tasting event with Tarara Winery and a denim trunk show featuring an array of wonderful jeans. Try on any 3 pairs of Jeans and get $20 off! Styles by Good American, Hudson, & DL1961.6-9 p.m.

Location: 5 W. Loudoun St.

Rock Songs. Balls of Glory, downtown’s newest restaurant, is hosting Buddy Cosmo, playing a wide range of rock songs from the past 40 years. At Balls of Glory, 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. 6-8 p.m.

Classic Rock. The 14 Loudoun bar and restaurant is featuring an outdoor concert by the band, My Generation, playing classic rock songs from the 60s through the 90s. Everyone will recognize the songs and will want to sing and dance along. 7-10 p.m.

Location: 14 Loudoun St. SE

Moon Photo Show. Medlin Art Gallery is hosting a special photography exhibit celebrating the 50th anniversary of the Apollo 11 Moon Landing. Stop by to check out these amazing photos! They are also showcasing a large selection of antique prints, maps and original artwork by nationally-known artist. Light refreshments served. 6-9 p.m.

Location: 2 Loudoun St. SE

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 6-8:30 p.m.


Acoustic Rock. Designer Goldsmith is featuring the acoustic guitar duo, Laurie Blue and Bill Rose, playing a variety of rock from the 60s through today that you can sing along with. 6:30-8:30 p.m.

Location: Market Station –Lower Level. 

Bluegrass Music and Art. Crooked Run Brewing is featuring live music with the Short Hill Mountain Boys, playing all kinds of good ole bluegrass music. They are also hosting an art exhibit by Hannah Cousland. 7-10 p.m.

Location: Market Station Lower Level.

Classic Rock. MacDowell Brew Kitchen is hosting an outdoor concert with the bodacious gents of Just South of 7. The band covers all the bases with music across five decades of rock. 5-9 p.m.

Location: 202-B Harrison St.

Free Yoga Lesson. Flow Yoga is offering a FREE fun-filled yoga practice, which is open to all experience levels.6-7 p.m.

Location: Market Station – 3rd floor.

Wine Tasting. Visit Loudoun is hosting a wine tasting event with Sunset Hills Vineyards. Light refreshments offered. 6-9 p.m.

Location: Market Station – Lower Level.


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. 6:30-10 p.m.

Loc: South King Street between Loudoun and Market 

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. 6:30-8:30 p.m.

DJ ZBreezy. Bites Wine and Grilled Cheese Bar is hosting music from DJ ZBreezy, on their front porch with an extended happy hour! 6-9 p.m.

Location: 105 S. King St.

Pop Music. SideBar is hosting pop singer-songwriter, Zach Benson, performing his fun, danceable songs for audiences young and old. His new original EP was released on Spotify and Apple Music and his EP of covers is available on bandcamp. 6:30-9:30 p.m.

Location: 24 S. King St.

Rock Band. The King’s Tavern and Wine Bar is hosting a fun concert on their back patio with The PBJ Band, a rock band featuring some long time musicians playing a wide range of awesome tunes from rock and folk to bluegrass and blues. 7-10 p.m.

Location: 19 S. King St.

Sax Music. Very Virginia Shop is hosting saxophonist, Manuel Estrada, a talented high schooler, performing a wide array of jazz, pop and rock tunes from yesterday and today. You can also taste free samples of over 20 different flavors of Virginia peanuts and other locally made gourmet foods. 6-9 p.m.

Location: 16 S King St.

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 art exhibit will be on display by their Artist of the Month, Desmond Herbert.

Location: 110 S. King St. 6-9 p.m.

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! 6-9 p.m.

Location: 107 S, King St.

DJ ZBreezy. Bites Wine and Grilled Cheese Bar is hosting music from DJ ZBreezy, on their front porch with an extended happy hour! 6-9 p.m.

Location: 105 S. King St.

Classic Guitar. The Leesburg Diner is hosting live music with classical guitarist, Chris Meyers, playing an array of classical music. 6-8 p.m.

Location: 9 S. King St.

Rock Band. Coldwell Banker is hosting live music with the rock band, Nailed It, playing an array of rockin’ fun tunes. Stop by to check out this fun group of guys playing rock songs from the past. 6:30-8:30 p.m.

Location: 25 S. King St.

Ukulele! Misguided Angels is hosting Lisa Olsen on baritone ukulele, playing stripped down rock and folk songs from the 60s through today. 6:30-8:30 p.m.

Location: 14 S. King St.

Brittany. The Lucky Knot, an ultimate preppy store with a nautical flair, is hosting Brittany Frazer, who plays acoustic guitar, and sings contemporary pop and rock songs from the past couple of decade. 6:30-8:30 p.m.

Location: 9 N. King St.

Rockabilly. Shoes Cup and Cork is featuring acoustic guitarist, Daniel McCurdy playing rock and pop tunes. 6-8:30 p.m.

Location: 17 N. King St.

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. 6-9 p.m.

Location: 34 S. King St.

Jazzy Tunes Georgetown Café is hosting vocalist, Larisa Mangione with her husband Chris, on guitar, along with some of her music students, all playing a wide array of jazzy and fun songs. 6-9 p.m.

Location: 19 S. King St. 

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!6-9 p.m.

Location: 36 S. King St.

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. 6 p.m.- 1 a.m.

Location: 19 S. King St.

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. 6-9 p.m.

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. 9 p.m.- midnight

Location: 10 S. King St.

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. 6-9 p.m.

Location: 27 S. King St.


Live Music. Trinity House Café is hosting guitarist, Andrew Renner some fun tunes to keep the night hopping! 6:30-8:30 p.m.

Location: 101 E. Market St. (corner of Market and Church St.)

Two Art Exhibits. The Tryst Gallery is featuring the premier reception of Neighbors: A Portrait Gallery by Joan Garcia along with the second reception for our Chill Pop Exhibition. Stop by to check out all the amazing artwork by over 40 local artists! Light refreshments. 6-9 p.m.

Location: 312 E. Market St.

Jazz Piano. Casa Nostra, downtown’s newest Italian restaurant, is hosting live music by the Bad Press band, featuring some great jazz tunes and R&B music. 7-10 p.m.

Location: 2 W. Market St.


Art and Wine. The Fine Gallery is hosting an open house celebration in honor of the 2nd anniversary. This gallery is equal parts contemporary art gallery and educational art provider, focusing on an immersive art learning experience. 6-9 p.m.

Location: 9 Royal St. SW


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. 6-9 p.m.

Location: 19 Wirt St.