Leesburg’s First Friday celebration kicks off with the town’s Tree Lighting ceremony on the Town Green at 6 p.m. Then there will be a full night of art exhibits, musical performances and family activities. In anticipation of a large crowd, King Street between Market and Loudoun streets will be closed to traffic from 6:30 to 10 p.m. 


Maddy! Trungo’s is featuring mezzo-soprano, Maddie Curtis, a graduate of Catholic University, where she studied Opera. Maddie is quite versatile, singing in all assortments of genres, having been in over 30 musicals. She was even on Season 9 of American Idol and went on to Hollywood. Maddy will be accompanied by Calab Nei on keyboard. 6:30-9:30 p.m. 2 W. Loudoun St.

Classical Tunes. Black Shutter Antiques is hosting classical guitarist, Jarrett Laskey, playing an array of classical music standards from the Beatles to Bach and Beethoven. 6:30-8:30 p.m. 1 Loudoun St. SE

Lee Jones! Bike TrAle Brewery is hosting live music with singer, Lee Jones, playing a variety of classic rock songs on banjo and guitar. Stop to hear some good tunes. 6:30-9:30 p.m. 101 Loudoun St. SE

Open House. Lou Lou Boutique is open late for Leesburg First Friday with an array of new winter fashions along with their new natural stone Frenzy jewelry collection, and ABLE bags, which are socially conscious and beautifully made. 6:00-9:00 p.m.  9 W. Loudoun St.

Live Art Demo. Loudoun Street Studios is featuring an art demonstration and their newest resident artist, Kim Richards, plus a curated selection of small artworks, just right for gift giving by artists, Beth Widom, Libby Stevens and Carol Buswell. Stop by to check out all the cool artwork by these very talented local artists and learn about their upcoming workshops. Light refreshments served. 6:30-8:30 p.m. 2A Loudoun St. SW (upper level).

Historic Holidays. The Loudoun Museum is hosting an open house inside the log cabin featuring holiday decorations and a display of historic Christmas cards and toys from the Museum’s collection. Also stop by to meet Old St. Nick and take a selfies with the jolly guy from 6:30-8:00. 5:00-8:00 p.m. 16 Loudoun St. SW.

Ugly Sweaters and More. The Embark Center for Self-Directed Education will be hosting a holiday celebration. The festivities will include a free screening of your favorite holiday movie, an ugly holiday sweater contest, holiday karaoke and more! All ages welcome. 6:00-9 p.m. 103 Loudoun St. SW

Photography Show. Photoworks is featuring an art exhibit by Bill Giarratana who has been involved in the arts for over 50 years. Experienced in a wide range of work from sculpting, illustrating, custom portraits and most recently abstracts. Stop by to see his amazing art! 6-9 p.m. 2A Loudoun St. SW

Art and Music. Art Sweet Art is hosting an art show entitled, Through the Lens, a photography exhibit, featuring contemporary imagery from Marc Sirinsky and Colleen Lewis. There will be beautiful classical guitar music by Aidan Pershong, along with delicious Belgian Chocolates. 6:30-9 p.m. 2B Loudoun St. SW

Jewelry Show. Madisonbelle is hosting a trunk show with Onyx & Oak, which is a jewelry line by designer, Rebecca Eagan, whose unique compositions of her jewelry is an expression of her creativity fueled by the diverse materials and textures she uses in each piece. Also free blowouts and lashes from Modern Concepts Salon via a appointment/reservation online. 3-8 p.m. 5 E. Loudoun St.

Meatballs! Balls of Glory, downtown’s newest restaurant, is open for Leesburg First Friday as they are experts in all things meatballs, so stop by to welcome this fun new eatery to historic downtown Leesburg.  6-10 p.m. 15 E. Loudoun St.

Holiday Fun. The 14 Loudoun bar and restaurant is featuring a night of holiday fun with their Fa La La theme of activities. 7-11 p.m. 14 Loudoun St. SE

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. 6-9 p.m. 2 E. Loudoun St.

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. 6-8:30: 212C Loudoun St. SE


Jazz and Art. Crooked Run Brewing is featuring live music with Kevin Johnson, playing an array of jazz music. They will also host an art exhibit by Andrew Kravatz. 7-10 p.m. Market Station – Lower Level.

Fun Night! MacDowell Brew Kitchen is featuring Panic for the Vibe, playing an array bass-driven grooves, reggae rhythms and soulful cadences, while alternating between funk, pop, blues and West Coast-reggae styles. 7-11 p.m. 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. Market Station – 3rd floor.

Wine and Art. Visit Loudoun is hosting a wine tasting event with Two Twisted Post Winery. They are also featuring art exhibit by the Friends of Leesburg Public Art with an array of artwork by local artists, Sabine Arndt, Chip Beck, Laura Hopkins, Donna Varney, and Barbara Wilson. Light refreshments offered. 6-9 p.m. Market Station – Lower Level.


Open House. A Wedding Loft is hosting an open house event to showcase their new collaborative destination space for wedding professionals and creatives, with daily workspace, podcast and photo studios & beauty stations, networking, education, mentorship and so much more. o 6-9 p.m. 11 S. King St.

Balloons, Music and Food. Very Virginia Shop is featuring Fancy the Clown, twisting and turning balloons into a work of art for your child’s amusement from 6-8pm. Plus live music with saxophonist, Manuel Estrada, a talented high schooler, performing an array of lively jazz tunes. You can also taste free samples of over 20 different flavors of Virginia peanuts and other locally made gourmet foods. 6-9 p.m. 16 S King St.

Holiday Tunes. SideBar is hosting live music with acoustic rock guitarist, David Goodrum, playing some holiday favorites, along with classic rock tunes from yesterday and today. Location: 24 S. King St. 6:30-9:30 p.m.

Santa vs The Grinch? Be Beauty is hosting a holiday photo event with Krysta Rene Photography, as she will take your picture with either Santa or The Grinch! Bring your nearest and dearest, including your pets, and get a digital image you can use and reuse forever for $25. Now that’s a deal the will cheer up the Grinchiest of Grinches! Location: 13 S. King St. o 6:30-10:30 p.m.

Music and Art. King Street Coffee is hosting acoustic guitarist, Gary Rudinsky, along with many talented students from the music department of Loudoun County High School. Plus, they are featuring paintings by Karen Mahan as part of their Artists of the Month program. Location: 110 S. King St. 6:00-9 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! Location: 107 S, King St. 6-9 p.m.

Jazzy Tunes. The Leesburg Diner 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. Location: 9 S. King St. 6-8 p.m.

Jazz Music. Coldwell Banker is hosting the Azure Jazz Combo, consisting of students from Stone Bridge High School, playing an array of jazz tunes. Location: 25 S. King St. 6:30-8:30 p.m.

Rock Duo. Misguided Angels is hosting the popular acoustic guitar duo, Bill Rose and Laurie Blue, playing a variety of rock from the 60s through today that you can sing along with. Location: 14 S. King St. 6-8 p.m.

Holiday Open House. The Lucky Knot, an ultimate preppy store with a nautical flair, is taking part in Leesburg First Friday with a special holiday sale, but please note, this does excludes Lilly Pulitzer and Barbour Formal items. Stop by to check out all their cool and hip fashion items! Location: 9 N. King St. 6-9 p.m.

Piano Music. The Brick and Mortar Store is hosting live piano music by students from The Catoctin School of Music. Stop by to check out this cool new shop on the corner. Location: 34 S. King St. 6:30-8:30 p.m.

Rock Trio. Georgetown Café is hosting featuring the teen rock trio, known as Arsenal Waves playing classic and modern rock tunes. Location: 21 S. King St. 6:30-8:30 p.m.

Santa. The Sunflower Shack is hosting Santa so bring the family by to meet Santa and his elves. Bring your camera so you can take a photo with him. Location: 36 S. King St. 6-8 p.m. 

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. 6:00-1:00

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.  9-12

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. 6-9 p.m. 


Caryn. Trinity House Café is hosting singer/songwriter, Caryn Switaj, who weaves together a unique blend of genres spanning Americana, folk, country and even some old time gospel with her warm soulful vocals. Location: 101 E. Market St. (corner of Market and Church St.) o 6:30-8:30 p.m.

Unapologetic. The Tryst Gallery’s new featured artist space is Unapologetic! This show features 15 female artists in a group show within a group show. Join them to celebrate these Unapologetic female artists, as they close off the year and welcome a new decade of art! Light refreshments. Location: 312 E. Market St. 6-9 p.m.

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. 7-10 p.m.


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 p.m.


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. 6 p.m.-9 p.m.