Leesburg First Friday

Stroll around historic downtown Leesburg on the First Friday of each month (except January), to enjoy numerous live music performances, art exhibits, wine tastings, book signings, open houses and so much more – all throughout downtown! Over 45 specialty shops, art galleries, and restaurants are open until 9pm or later, many offering free refreshments and/or special sales.

The date for the next Leesburg First Friday event is OCTOBER 3, 2025. Be in the loop about what is going on each month by liking the LEESBURG FIRST FRIDAY page on FACEBOOK. The dates for the YEAR 2025 are 2/7/25, 3/7/25, 4/4/25, 5/2/25, 6/6/25, 7/11/25*, 8/1/25, 9/5/25, 10/3/25, 11/7/25, and 12/5/25. (Please note that there is no Leesburg First Friday event in January, as it is the only month we skip). Save these upcoming dates for next year as the dates for the year 2026 are 2/6/26, 3/6/26, 4/3/26, 5/1/26, 6/5/25, 7/3/26, 8/7/26, 9/4/26, 10/2/26, 11/6/26, and 12/4/26.

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

The events for OCTOBER 3 are in the middle of being updated below. The best way to be in the loop about activities happening each month is to follow the LEESBURG FIRST FRIDAY facebook page.

  • NORTH KING STREET:

    • Fabulous Restaurant. The Lightfoot Restaurant is not hosting live music this month, but will join in the Leesburg First Friday activities in future months. You can still come on in for a fabulous meal!
      Location: 11 N. King St.
    • 6:00-9:00 Open House. R and B Tattooing and Dominion Body Piercing are open late with an open house to celebrate their new location above the Downtown Saloon. Many people say they are the best tattoo and piercing place around!
      Location: 7A N. King St.
    • Not this Month. The King Street Experience is skipping this month but will join in again for other upcoming months.
      Location: 107 N. King St.
  • MARKET STREET:

    • 7:00-10:00 Rooftop Music. The Crow’s Nest, downtown's only rooftop bar, is hosting live music with the fun Cowpoke Band, singing from the rooftop - literally!.
      Location: 7 W. Market St.(above Buford’s Biscuits)
    • Open House Moved to Next Month. The NOVA Creative Reuse Center had to change the date and will now be hosting their first open house at the November First Friday on 11/7, to celebrate their move into their new location downtown - the building where CRAFT used to be. Stop by to shop all the really cool craft supplies that they offer and support this great non-profit, which is dedicated to promoting creative reuse.
      Location: 3 W. Market St.
    • 6:00-9:00 Local Music and Brews! The Loudoun Brewing Company is featuring live music with with rock band, 2MB, playing an array of cool rock tunes. Stop in for some great brews and great music.
      Location: 310 E. Market St.
    • Dessert Cafe! Mocatinas, downtown’s dessert heaven, has a wonderful array of awesome desserts for you to choose from, along with some great ice cream flavors.
      Location: 3 E. Market St.
    • 6:30-8:00 Author Event.The Birch Tree Book Store is featuring an author event with M.K. England and Natalie Naudus, discussing M.K.'s sapphic romance and her first adult novel - All Fired Up. Birch Tree is a unique independent book store, so come check out their huge collection of books. Plus be sure to stop into the Foliage Plants Shop, as it is a shop within a shop!
      Location: 11 W. Market St.
    • 6:00-8:00 Open House.The District Hemp Botanical is staying open late for First Friday with an array of special new products.
      Location: 9 W. Market St.
    • 10:00-5:00 Art on Display. The Leesburg Commission on Public Art (COPA) is pleased to announce a new art exhibit currently on display on the first floor of Leesburg Town Hall. Chip Beck is showcasing a display of watercolors that capture historic Hillsboro, locations throughout Loudoun County, and highlights from his travels abroad. The exhibit will run through November 2025 and can be viewed in-person Monday through Friday, from 8-5pm. An open house will be held on Friday, November 7, from 5 to 6pm for those interested in meeting the artist.
      Location: 25 W. Market St.
  • LOUDOUN STREET:

    • 6:00-9:00 Rock Tunes. Dynasty Brewing Company is hosting rock guitarist, Chris DeSantis, playing your favorite rock songs from the past. Stop in for some great locally crafted brews and live music!
      Location: 101 Loudoun St. SE
    • 6:00-8:00 Open House. Resourceful Woman will be open late for this month's Leesburg First Friday events, so you can come by to help support all the good they do for our local community!
      Location: 11-A Loudoun St. SW
    • New Mexican Restaurant. The Casa de Avila, downtown’s new taco restaurant, is hosting live music with saxophonist, Manuel Estrada, performing an array of lively jazz and contemporary songs. Come on in to try some of their amazing dishes!
      Location: 2C Loudoun St. SW
    • 5:00-7:00 Not this Month.The Embark Center for Self-Directed Education is not open late for this month's First Friday, but will be back in other months.
      Location: 103 Loudoun St. SW
    • 6:30-9:30 Rock-n-Roll! Schmidt’s BBQ is hosting live music on their fun backyard patio with the rock band, Trolling for Olives, playing an array of classic rock tunes. Come enjoy some great local BBQ, while listening to some great live music!
      Location: 14 Loudoun St. SE
    • 5:00-7:00 Fashion Open House. Madisonbelle, who recently celebrated their 20th anniversary, is hosting an open house until 7pm. Come check out all their new fabulous fall fashion pieces!
      Location: 5 Loudoun St. SE
    • 5:00-7:00 Leesburg’s Anniversary. The Thomas Balch Library is hosting an event to celebrate the 276th anniversary of Leesburg, established on  October 12, 1758. Stop by the Donaldson Log Cabin (14 Loudoun St. SW) for a pop-up exhibit showcasing the important role local businesses and technologies have played in shaping Leesburg’s growth and community life through historic records from the Thomas Balch Library’s collection. A highlight will be a slide projector show featuring photographs from the 1970s–1990s, along with examples of business ephemera spanning the town’s history.
      Location: 14 Loudoun St. SW
    • 6:00-8:00 Open House. Books And Other Found Things is hosting an open house, so you can explore their thousands of used and new book for adults and children.
      Location: 13 W. Loudoun St.
    • 5:00-7:00 Local Art. Muz and Rose is featuring local artist, Emily Giuffre, as their "artist of the month" and see her unique art display, as she wants to show God's beauty in this world.
      Location: 3 Loudoun St SW
    • Unique Gifts. wldwst features a wide array of local artwork and unique gifts, so be sure to stop in and check out all their very cool items.
      Location: 2B Loudoun St. SW
    • 5:00-7:00 Candy Jar. The Loudoun Museum is hosting a contest so be sure to stop by to guess the amount of candy in the jar. The closest guess a free Hauntings ticket! A winner will be contacted on October 6th. Also you can check out their unique local historic pieces out on display and their latest themed history exhibits. The museum is completely free and all ages are welcome.
      Location: 16 Loudoun St.
    • 6:00-9:00 Wine Tasting with Music. The October One Tasting Room is hosting wine tasting with an array of their fabulous wines. Plus this month they are hosting live music with the fabulous guitarist, Ramaan Insari.
      Location: 7A Loudoun St. SW
    • 6:00-8:00 Candle Making. The Global Local is hosting a candle making workshop, along with a curated wine tasting event.
      Location: 102 Loudoun St. SW
    • 5:00-7:00 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. 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 all types of vinyl records and cassette tapes.
      Location: 212C Loudoun St. SE
  • MARKET STATION AREA:

    • Wine! Gvino Enoteca, a fine wine boutique and restaurant, is hosting wines from around the world, in their shop located on the lower level of Market Station. Stop by to check out his vast array of international wines.
      Location: Market Station
    • 6:00-9:00 Live Music. Designer Goldsmith is hosting live music with the rock duo, Jan and Jeff, playing classic rock tunes, that you can sign along to. Plus stop inside to see all the fabulous fine jewelry, that she custom makes, right here in her shop.
      Location: Market Station
    • 6:00-9:00 Wine and Art. Visit Loudoun is hosting a wine tasting event with Three Creeks Winery, along with an art display by Eva McKinley.
      Location: Market Station – Lower Level.
    • 7:00-10:00 Cider Tasting. The Wild Hare Hard Cider Cabin is featuring their wide array of delicious ciders, all locally made.
      Location: Market Station – Lower Level
    • 7:00-10:00 Music and Art. The Crooked Run Brewing is featuring live music with acoustic guitarist, Luke Johnson, playing some cool Mountain Soul Music. Plus they feature art displays by different local artists.
      Location: Market Station - Lower Level.
    • 6:00-9:00 Escape Room. The Escape Room LoCo is hosting a fun escape room activities so you can stop by and try to find your way out of the mysteries, they have in store for you and your friends.
      Location: 201 Royal St. SE
  • SOUTH KING STREET:

    • 6:30-8:30 Rock Guitarist. Georgetown Café is hosting rock guitarist, Joe Reiman, playing some great songs that you can sing along to.
      Location: 21 S. King St.
    • 6:00-8:00 Open House. Misguided Angels, a fashion boutique, is hosting an open house, featuring their unique array of new fall fashions and accessories - that just arrived!
      Location: 14 S. King St.
    • 6:30-8:30 Book Signing and Food Tasting The Very Virginia Shop is hosting a food tasting event with local BBQ sauces. Also a book signing event, so you can meet the author, Donn Dobkin and his local photography book. There is also art on display by Peggy King and Kathy Bleau, along with dog treats by ECHO, a local non-profit. Plus you can taste free samples of over 20 different flavors of Virginia peanuts and other locally made gourmet foods.
      Location: 16 S King St.
    • 6:00-9:00 Live Music. SideBar is hosting the acoustic duo, Crossing Elden playing some classic rock and contemporary tunes.
      Location: 24 S. King St.
    • 6:00-1:00 Rock All Night. King's Tavern and Wine Bar is hosting the Andy Hawk and the Train Wreck Endings, playing some cool tunes to go along with your cool drinks and hot food. Afterward, from 9:30 to 1:00am, there will be an open mic night, hosted by Laurie Blue, with lots of local musicians. Plus the baddest Dad band known as The Black Minivan, will be rockin’ outside from 6:30 to 9:30 on the party patio out back.
      Location: 19 S. King St.
    • 5:00-9:00 Sidewalk Dining. The Town of Leesburg hosts the Sidewalk Dining Program on Friday evenings in the summer months, in historic downtown Leesburg, so restaurants on both sides of the street can put tables out for a fun eating outside experience. One block will be closed to vehicular traffic on South King Street from Market Street to Loudoun Street.
      Location:One Block
    • 6:00-10:00 Italian Disco Night. The GooseCup Coffee and Bar is serving specialty coffee (they roast), proper cocktails and small bites. They have a nice big patio for you to enjoy outside while sipping your hot coffee and cool drinks! They are featuring an Italian Disco Night for October's First Friday, so come dance the night away!
      Location:216 S. King St.
    • 8:00-11:00 Live Music. The Green Tree Tavern is featuring their fun sport bar with a cool atmosphere for meeting friends, while enjoying good food and drinks. For this First Friday, they are hosting the rock band, File a Compliant with Craig Green, who will be rockin’ your favorite tunes. Come check out this popular night spot!
      Location: 15 S. King St.
    • 6:00-9:00 Wizard World Event. Move Leesburg is hosting Wizarding World with tons of wizard themed activities, so you can join them for a FREE magical market filled with fun for witches, wizards, and muggles alike! Some of the activities include Make your own Patronus necklace, Design your very own Dobby sock, Pot your own mandrake, Grab a wizard hat & glasses and enjoy coloring, temporary tattoos & more! Don’t miss their Wizarding Costume Contest so dress to impress for a chance to win a $25 gift card to Wonder! Huge thanks to Wonder for sponsoring this magical prize. Be sure to check them out for even more enchanting finds! Plus, shop a variety of enchanting vendors while soaking in the wizarding vibes!
      Location: 11B S. King St.
    • 7:00-10:00 Speakeasy. Tarbender’s Lounge is a hip speakeasy bar and restaurant, that offers a cool atmosphere inside for dining and relaxing with friends, while listening to while listening to some cool jazz music by The Reliable Trio, in the background.
      Location: 10 S. King St.
    • 5:00-7:00 Art Exhibit.The Ordinary Art Gallery is hosting a unique collection of art by the owner, along with other fabulous local artists.
      Location: 18 S. King St.
    • 6:00-9:00 Live Music. Ebisu Sushi and Thai Restaurant is hosting acoustic guitarist, Gary Rudinsky, playing an array of classic rock tunes from the past several decades.
      Location: 101 S. King St.
    • 6:00-9:00 Wine and Music. The Leesburg Gourmet is featuring a chocolate and rose wine pairing event, featuring their select wines and Neuhaus Belgian Chocolates. Plus this month they are hosting electronic artist, Cycle J with guitarist, Cary Birkitt.
      Location: 27 S. King St.
    • 6:00-8:00 Cats, Treats and Music. Coldwell Banker Realty is hosting a bake sale by students of Loudoun County High School, so stop by to get lots of yummy treats. Plus a cat adoption event, so you can rescue a cute cat for your very own. Also there will be live jazz music by the Josie Jazz Combo, featuring a trio of talented students, performing some lovely tunes.
      Location: 25 S. King St.
    • 6:00-9:00 Super Yummy! 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.
    • 6:00-9:00 Wine Lounge. The Echelon Wine Bar is featuring Themed Wine Flights, as a special event for Leesburg First Friday.
      Location: 32 S. King St.
    • 6:00-8:00 Open House. The Sunflower Shack is open late for Leesburg First Friday with an open house, showcasing their many fun and old-fashioned candies. Stop in to shop their wide array of old fashioned candies, sodas, and other various nostalgic gifts.
      Location: 36 S. King St.
    • 6:00-9:00 Open House. The Brick and Mortar Mercantile Store is hosting an open house with their curated collection of fun lifestyle gifts.
      Location: 34 S. King St.

Live Music Events
Art Exhibits
Wine Tastings

... and so much more!