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leonardtown a&e 

Leonardtown Maryland, the only ARTS & ENTERTAINMENT DISTRICT in Southern Maryland, offers a rich experience in culture. Explore art galleries, see shows and attend art shares with upcoming and prominent artists, take group or one-on-one art classes, and create your own work of art in instructor-led workshops.
Sign up for the Leonardtown A&E Newsletter or check this page often for upcoming events and activities.


Upcoming Special Events


Classes & Workshops


Entertainment Venues

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Leonardtown A&E The Show


Upcoming Events & Activities

Leonardtown offers an exciting variety of events and activities. Whether you're looking for a fun way to occupy the kids, a way to spend a creative outing with friends or a fun date-night event, you're sure to find it here in Leonardtown. Here's a highlight of wonderful events and activities that are taking place this season in Leonardtown.

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Bethany Yeh Performance in LTown Alley

June 2, 2023
5 p.m. - 6 p.m.

Local artist, Bethany Yeh, performs an acoustic set in LTown Alley during Grillin' & Chillin' First Friday from 5 p.m. - 6 p.m. on June 2nd (sponsored by the Leonardtown Arts & Entertainment District). Enjoy FREE art activities and a classic and antique car display in the Alley while enjoying the music.

Learn More

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Live Music from Joseph Norris

June 2, 2023
6 p.m. - 9p.m.

Enjoy live music from Joseph Norris and a good old-fashioned cookout in Leonardtown Square during Grillin' & Chillin' First Friday on June 2nd from 6 p.m. - 9 p.m. The evening also features FREE art activities and classic & antique cars on display in LTown Alley.
Learn More

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R&B Line Dancing

June 24, 2023
5 p.m. - 8 p.m.

Enjoy R&B Line Dancing during the On the Water's Edge Concert with Latrice Carr and the Rise Band & Show on Saturday, June 24th at the Leonardtown Wharf. Dance enthusiast and instructor, Renee Stevens, teaches fun and easy-to learn routines throughout the evening
(the concert is from 5 p.m. - 8 p.m.). Enjoy learning the latest dances and practicing your moves to fabulous
live music.

Learn More


Latin Nights in Leonardtown

New Dates for 2023
Various Times.


Learn popular Latin dances - Bachata, Kizomba and Salsa from talented dance instructors -Tracy Hurtt and Robin Santiago at local businesses - Antoinette's Garden, Port of Leonardtown Winery, and Leonardtown Cigars.

 Learn More

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Drum Circles

First Friday's
Returning Spring - Fall


The St. Mary's County Arts Council and the SoMar Drummers partner to frequently hold community drum circles during First Friday events. The community is invited to participate - no experience required. Percussion instruments are provided and you're welcome to bring your own. Follow the St. Mary's County Facebook Page for upcoming dates and times.

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Classic & Antique Car Display

June 2, 2023
5 p.m. - 8 p.m.

View classic & antique cars on display in LTown Alley during Grillin' & Chillin' First Friday on June 2nd from 5 p.m. - 8 p.m. courtesy of St. Mary's County Rod & Classic. Enjoy live music throughout the evening while viewing the cars and meeting their owners.

Learn More

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Health & Wellness Classes

Many continuing from June through October
Various Times

Stay fit with a variety of outdoor, group health & wellness classes. Choose from Pilates and stroller fitness classes with SPICE Studio, SUP Classes and kids summer camps with root, SUP & Fitness, yoga with Evolve Yoga & Wellness and Zumba and Line Dancing with Zumba Fitness Around Town, and much more! Learn more about health & wellness and other events by joining the Leonardtown A&E News email list.


2nd Annual Leonardtown Sidewalk Art Contest

Saturday, September 2nd
10 a.m. - 5 p.m.

Express your creativity at the 2nd Annual Sidewalk Art Contest at the Leonardtown Wharf on Saturday, September 2, 2023. Create your artwork anytime between 10 a.m. – 3:30 p.m., judging will take place from 3:30 p.m. – 5 p.m., and the winners will be announced at the On the Water’s Edge Concert at the Wharf featuring Phillip Michael Parsons later that evening at 5 p.m. Great cash prizes and gifts will be awarded (tba and you must be present to win). This event is FREE and open to all levels from kids to adults. Choose to participate in four categories: PRO, DABBLER, YOUTH or FAMILY. For more information or to register for FREE below: 

Register Here

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Coastal Arts Market

Spring & Fall Markets
Returning Spring & Fall


Shop with local artists, crafters and artisans during the open-air markets at the Leonardtown Wharf - returning on April 15th. 

Learn More


Zumba Fitness Around Town

April - October
Saturdays 9 a.m.


Group dance fitness classes offered around Leonardtown. Join other dance enthusiasts and enjoy classes, parties workshops and special events. Kicking off on Saturday, April 15th with a Spring Launch Party (Zumba from 9 a.m. - 10 a.m. New this season, the first Saturday of every moth will be R&B Line Dancing with Renee Stephens. For more information contact Leslie at: 301-247-7012

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FREE Make & Take Activity

June 2, 2023
5 p.m. - 8 p.m.

Enjoy a FREE Make & Take activity with Tape a Friend, Make a Friend, an organization that helps kids strengthen their self esteem through art and positive messages, in LTown Alley on Friday, June 2nd from 5 p.m. - 8 p.m. for Grillin' & Chillin' First Friday (sponsored by the Leonardtown Arts & Entertainment District). This family-friendly project is best for ages 5 - 12, but all are welcome.

Learn More

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Kids Summer Camps

Beginning in June
Various Times

Looking for summer fun for the kids? There are plenty of kids camps to keep your little ones engaged and happy this summer. They can explore their creativity in summer art programs at The Yellow Line Studio, learn the FUNdamentals of golfing with Above Par Golf & Entertainment, and learn water safety and standup paddleboard techniques at the root, SUP & Fitness kids SUP camps at the Leonardtown Wharf.
Learn more about fun activities for kids this summer by joining the
Leonardtown A&E News email list.

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Fall Plein Air
at the Wharf

Friday, September 22, 2023
4:30 p.m. - 7:30 p.m.

Celebrate the First Day of Autumn and capture the beauty of the Fall at the Leonardtown Warf on Friday, September 22nd. Bring your own supplies take part in a free art class with Carrie Patterson, professional artist, Professor of Art at St. Mary's College and owner of the Yellow Line Studio in Leonardtown. Enjoy live music while sampling award winning wine, tasty eats and sweet treats (this event is free and open to the public. Food, drink and ice cream are available for sale with participating businesses).

For more information call 301-475-9791


Movie Fest

Saturday, October 21
5:00 p.m. - 8:30 p.m.


Calling all ghosts and ghouls, ninjas and ballerinas, join us for an exciting evening of Halloween fun at the Leonardtown Wharf (State Hwy 326, Leonardtown, MD 20650) when the Town of Leonardtown presents the Leonardtown Halloween Movie Festival on Saturday, October 21st from 5 p.m. - 8:30 p.m. (move TBA). This event is FREE and open to the public. For more information call 301-475-9791


The Mad Splatter Shack Immersive Paint Experience

June 2, 2023
6 p.m. - 8 p.m.

Join us for the premiere of the Mad Splatter Shack, an immersive splatter paint experience, with Cam Donohue in LTown Alley during Grillin' & Chillin First Friday on June 2nd from
6 p.m. - 8 p.m. (this activity is offered for FREE during First Friday courtesy of the Leonardtown Arts & Entertainment District). This fun, family-friendly experience is for all ages! Meet Cam from 4:30 p.m. - 5:30 p.m. at the St. Mary's County Arts Council
on Washington Street.

Learn More

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R&B Celebration
at the Wharf

June 24, 2023
5 p.m. - 8 p.m.

The Town of Leonardtown and the Leonardtown Business Association are proud to present an R&B Celebration for the On the Water's Edge Concert Series at the Leonardtown Wharf, sponsored by Jimmy Hayden of RE-MAX 100 and Homes for Heroes, featuring Latrice Carr and The Rise Band & Show. The Rise Band and Show kicks off the celebration from 5 PM - 6 PM and Latrice Carr takes the stage from 6 PM - 8 PM. The evening also includes R&B Line Dance Instruction with Renee Stevens.

Learn More


Town Market LLC

Saturdays & Sundays
Various Times

Shop fresh local produce, meats, cheeses, breads, desserts and specialty items from local artists and crafters in this weekend open-air market on Saturdays starting at 9 a.m. & Sundays starting at 10 a.m.

Learn More


Drumline Jam & Drum-off

First Friday's
Returning Spring - Fall


The St. Mary's County Arts Council and the SoMar Drummers partner to frequently hold Drumline Jam & Drum-off showcases during First Friday events. Follow the St. Mary's County Facebook Page for upcoming dates and times.

Ongoing Classes & Workshops


Leonardtown offers a variety of ongoing classes and workshops that provide the perfect opportunity to explore your creative side while connecting with friends. View the local studios below that offer both public and private classes, workshops and events. A&E Month is the perfect time to explore your creative side.


Board & Brush

A creative studio featuring DIY workshops where you can create and connect with friends. Choose from a variety of projects including decorative wall art,  clocks, serving trays and more.

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The Yellow Line Studio
Professional Artist and Art Professor at St. Mary's College offers original art projects, workshops and classes for kids, teens and adults.


Wine & Design
Public and private sip and paint parties for all ages, groups and talents. 


Entertainment Venues

There's an exciting destination around every corner of Leonardtown. Sample award-winning wine while listening to live music, enjoy specialty cocktails while watching your favorite movie with friends, or experience Viking axe throwing in a beer garden. That and more awaits you at one of our thrilling entertainment venues below.


The Leonardtown Wharf

Various Weekends
Dates/Times Vary

The  picturesque waterfront park with a spectacular view is an exciting destination any day, but now you can take in an outdoor concert (the new music series, "On the Water's Edge", sponsored by Jimmy Hayden of RE/MAX 100, launched this year and now features exciting free concerts from Spring to Fall. Also new this year are outdoor plein air painting events. To learn more about upcoming events and happenings at the Wharf follow the Leonardtown Wharf Facebook page.



Live music, art workshops, Salsa events and more at POL Winery

Most First Fridays, Saturdays and Sundays

Enjoy an eclectic mix of performers in a wide range of genres including pop, country, rock, and more. Sample award-winning wine or slushies while you listen.  POLW also frequently hosts art workshops and Salsa events (part of the Latin Nights series). Follow the Port of Leonardtown Winery Facebook page to learn about upcoming performances and special events.

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Live music and special events at
The Rex

Various Weekends
Dates/Times Vary

The Rex Restaurant and Bar is a popular location for live entertainment. They frequently host bands on the weekends on their open patio. In the past, they've featured a wide range of bands performing a variety of music from rock and pop to country and jazz. The Rex also frequently holds trivia and from time-to-time karaoke nights. Follow The Rex Facebook Page to learn about upcoming performances and special events.


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Live music, comedy, reading club and more at Antoinette's Garden

Dates/Times Vary

Antoinette's frequently features live music on the weekends. Enjoy live jazz, R&B, pop, and soft rock music in the Garden while sampling wine and specialty cocktails. Antoinette's has also hosted comedy nights, book clubs and more special events. Follow the Antoinette's Garden Facebook Page to learn about upcoming performances and happenings.


Live music and special events at
SOF Market

Various Weekends
Dates/Times Vary

 Shepherd's Old Field (SOF) Market is a one-of-a kind indoor marketplace featuring over 65 specialty shops and service providers. You can fill a day browsing and shopping fabulous artwork and creations from local artists and crafters. SOF often hosts live music for shoppers to enjoy while browsing. They frequently host special events and activities (some past events have included Mother-Daughter teas, fashion shows, scavenger hunts and craft activities). Follow the SOF Facebook Page to learn of upcoming events and activities.

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Live Music, Movie Screenings and more at

Various Weekends
Dates/Times Vary


Social Coffeehouse has from time to time hosted live acoustic music. They also regularly host movie nights and themed parties. Enjoy draft beer and specialty cocktails with your entertainment. Follow the Social Coffeehouse Facebook Page for info on upcoming special events.


Live music and special events at
the Brudergarten

Various Weekends
Dates/Times Vary

 The Brudergarten indoor/outdoor beer garden is a popular bar/entertainment venue inside Shepherd's Old Field Market that frequently hosts live music and unique special events like Viking Axe Throwing, Bruderfest (Bru's version of Octoberfest complete with Weiner Dog Races, Stein Lifting Contests and more), and much more. Enjoy local craft beer, specialty drinks and tasty eats while playing games and soaking up the high energy and cool vibes. Join the Brudergarten Facebook Page to learn about upcoming events and happenings,


Arts & Entertainment the Show

Now Leonardtown Arts & Entertainment is a virtual show. Meet local artists, see art demonstrations and behind-the-scene looks at exciting A&E events in Town in the virtual show: Leonardtown A&E!

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In this episode of Leonardtown A&E Artist Spotlight, we meet local singer/songwriter and musician Bethany Yeh. Bethany has performed the National Anthem for many of Leonardtown's special events over the years including Veterans Day, Christmas on the Square, the Leonardtown Earth Day Celebration and more. She has also performed as "Alice" for the Alice in Leonardtown event in celebration of the beautiful mural created in LTown Alley by artists Tom Rogers and Dan Ropp, which is loosely based on Lewis Carroll's beloved book and the subsequent Disney movie, Alice in Wonderland. Bethany will be the first featured artist in LTown Alley during Leonardtown's Grillin' & Chillin' first Friday on June 2nd from 5 p.m. - 6 p.m.

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On the series premiere, we'll introduce you to Eric Jackson, the talented local artist who created the beautiful butterfly banners and flags that mark the newest addition to Leonardtown - the Leonardtown Butterfly Trail. Learn about Eric and the inspiration behind his beautiful works of art that are on display along the Trail and see highlights from the Butterfly Trail ribbon cutting ceremony, held on Sunday, July 11th, on the premiere of Leonardtown A&E Artist Spotlight!

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The Leonardtown Arts & Entertainment District is proud to present a special edition of the Leonardtown A&E Artist Spotlight series featuring the life and work of renowned American Photographer, Robert H. McNeill, in honor of Black History Month.

Join us for the premiere of this exciting, two-part series today at 11 a.m. on Wednesday, February 15, 2023 here:


Part 1 / Part 2





Maribeth Boeke Ganzell. Maribeth is a local Batik artist who was recently featured in the North End Gallery Artist Invitational. In the last episode we met artist Eric Jackson who created the beautiful butterfly banners for the Leonardtown Butterfly Trail using batik artistry. In this episode, Maribeth helps share the origins of batik and gives a demonstration of her latest work of art.




In this Feature Presentation, popular Southern Maryland Singer/Songwriter, Latrice Carr, performs at Il Piccolo Morso, an elegant new Italian Restaurant and entertainment venue located on Washington Street near Leonardtown Square. Accompanied by jazz guitarist, Alex Bizzro, Latrice entertains the crowd with sophisticated stylings of popular R&B, Rock, Country and more in this intimate performance. This video also provides a behind-the-scenes look at Il Piccolo Morso and features expert guidance on wine selection from the Port of Leonardtown Winery.

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In the premiere of Leonardtown Arts & Entertainment the Show, local Country Singer/Songwriter/Musician, Phillip Michael Parsons gives an exciting, up-close and personal acoustic performance at the Old Towne Pub. Learn more about Phillip and his music and get behind-the scene look at one of Leonardtown's most popular restaurants and entertainment venues.

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