LEONARDTOWN, Md. — Leonardtown is set to host a full weekend of events as First Friday kicks off the “Vintage Vibes Weekend,” bringing live music, shopping, family activities, and themed events to town from May 1 through May 3.
Festivities begin Friday evening with live music in the Square, art show openings, and a variety of activities throughout town. A free trolley will run from 5 p.m. to 10 p.m. to help visitors get around.
Saturday features a full day of events including vendor markets, sidewalk sales, and Star Wars-themed activities at participating businesses. The weekend wraps up Sunday with family-friendly events, shopping, and entertainment.
📍 Schedule of Events
Friday, May 1st
10am – 2pm | Popcorn Friday at Sneade’s
10am – 7pm | Old Jail Museum (extended hours)
5pm – 5:30pm | Drum Circle (SoMar Drummers)
5pm – 7pm | FREE Butterfly Craft
5pm – 8pm | Art Show Openings & Butterfly Trail Launch
5pm – 10pm | FREE Leonardtown Trolley
5pm – 10pm | Spring Festival (Fairgrounds)
6pm – 8pm | Live Music in the Square (Jack Allen)
7pm – 10pm | Music Bingo (Leonardtown Cigars)
7pm – 10pm | Live Music (Brudergarten)
8:30pm | Live Music (Action Lounge)
9pm | DJ Party at The Rex
Saturday, May 2nd
All Day | Star Wars Weekend Fun at Participating Businesses
9am – 4pm | Vendor Market & Yard Sale (Town Market)
10am – 10pm | Spring Festival
11am – 3pm | Sidewalk Sale (Arts Council)
6:30pm | Bath Meditation
8pm | Karaoke (Action Lounge)
8pm – 11pm | Live Music (Brudergarten)
Sunday, May 3rd
10am – 5pm | Book Signing (Fenwick Street Used Books)
10am – 6pm | Spring Festival
12pm – 8pm | Free Games (Action Lounge)
12pm – 9pm | Bucket Specials (Olde Town Pub)
2pm – 5pm | Family Skate (Leonard Hall Rec Center)
Organizers encourage visitors to spend the day — or the entire weekend — exploring everything Leonardtown has to offer, from locally owned shops and restaurants to live entertainment and family-friendly activities spread throughout town.
With a mix of vintage-themed experiences, Star Wars fun, live music, markets, and interactive events, the weekend is designed to offer something for all ages. Attendees can hop on the free trolley to easily navigate between destinations, discover unique finds, and take part in special events hosted by local businesses and community groups.
Whether you’re looking to shop, enjoy live performances, or simply spend time with family and friends, Leonardtown’s First Friday and Vintage Vibes Weekend offers a lively and welcoming atmosphere to kick off the month.
For complete details and updates, visit VisitLeonardtownMD.com.
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