September 2022 marks the 9th Anniversary of Leonardtown receiving its designation as an Arts & Entertainment District. It holds the honor of being the only A&E District in Southern Maryland. The Town will mark the anniversary with a series of exciting events and happenings throughout the Town for the entire month of September during what's being called "Leonardtown A&E Month". You'll find a variety of thrilling events including concerts, art shows, sidewalk art and plein air events and much more all September long!
View a highlight of Leonardtown A&E Month events and activities below and Download the Leonardtown A&E Month Itinerary to view a list of more exciting activities throughout Town!. Visit this page and/or join our A&E News email list to stay up-to-date on exciting events and activities taking place in Leonardtown.
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 during A&E Month in Leonardtown.
Salsa on the Vine in September
Thursday, September 15, 2022
6 p.m. - 9:30 p.m.
Enjoy an evening of Salsa dancing at the Port of Leonardtown Winery with Robin Santiago. The evening will begin with a beginners class (30-45min). Learn basic steps, leading, following, ladies turn, gentleman's turn, up to cross-body lead. Sample award-winning wine, wine slushies and more.$30/pp. This special event takes place on a Thursday instead of the usual Friday date in honor of the first day of Hispanic Heritage Month!
Leonardtown Summer Music Festival Presents: Reagan Years
in the Square
Friday, October 14, 2022
6 p.m. - 9 p.m.
The Leonardtown Summer Music Festival hosts an exciting concert in Leonardtown Square featuring the original 80's Tribute Band, The Reagan Years. This fun-filled event is the grand finale of an exciting season of the Leonardtown Summer Music Festival.
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.
Plein Air at the Wharf in September
Friday, September 16, 2022
4:30 p.m. - 7:30 p.m.
Capture the beauty of Leonardtown Wharf as the warm colors of the Fall begin to show at the Plein Air at the Wharf in September. Enjoy an evening of painting beautiful Breton Bay at the Leonardtown Wharf. Bring your supplies for the FREE open paint (advance registration is not required, but please contact email@example.com to be entered into the prize drawing - prize TBA) or attend a beginner's class with professional artist, Carrie Patterson - $55/pp - all supplies and instruction provided, must be at least 14 yrs old to participate (purchase tickets). Sample award-winning wine from the Port of Leonardtown Winery, tasty eats from Linda's Café on the Go and Farm.Fork.Soul, and sweet treats from Frog Town ice cream shop, and paint while listening to the smooth jazz stylings from the GrooveSpan Trio!
The Leonardtown Summer Music Festival
Leonardtown hosts a summer of exciting concerts featuring the Robbie Boothe, Latrice Carr, Leonardo Garcia & Son Horizonte, Blazin Keys Dueling Piano, Reagan Years and more throughout the Town of Leonardtown, Maryland from April - October 2022.
Join us for an exciting Summer of Music
Latin Nights in Leonardtown
Starting in May
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.
This exciting series kicks off on Saturday, May 14th. Learn More
Leonardtown Summer Music Festival Presents: The Leonardtown Throwdown Artist Showcase at POL Winery
Saturday, September 17, 2022
2 p.m. - 5 p.m.
The Town of Leonardtown and Port of Leonardtown Winery are proud to announce another fun, FREE concert. Join us for an exciting afternoon of music among the vines on September 17th from 2 PM - 5 PM when Justin Myles, Wes Ryce, Greg Barrick and David Hamner perform in the Leonardtown Throwdown Artist Showcase. Sample award-winning wine and slushies as you kick back and relax at the Port of Leonardtown Winery while Enjoying a great mix of rock and Country music from these talented artists.
Coastal Arts Market
Spring & Fall
Outdoor monthly marketplace that takes place throughout the Spring and Fall at the Leonardtown Wharf on Saturdays from 9 a.m. -
3 p.m. The Spring Market is held from April -June and the Fall Market will take place in October and November. Visit the CAM website for more information and upcoming dates.
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 23rd with a Spring Launch Party (Zumba from 9 a.m. - 10 a.m. followed by Line Dancing from 10 a.m. - 11 a.m.). For more information contact Leslie at: 301-247-7012
Leonardtown Sumer Music Festival Presents: The Bootleggers Band at the Fenwick Inn
Sunday, September 18, 2022
4 p.m. -6 p.m.
The Bootleggers will be performing at the Fenwick Inn on Sunday, September 18th from 4 p.m. - 6 p.m. Gates open at 3:30 p.m. Please bring a blanket or lawn chair to enjoy the show. There will be a cash or credit bar during the show!
Drumline Jam & Drum-off
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.
Download the Leonardtown A&E Month Itinerary to learn about more great A&E events taking place in September
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.
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
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.
Live music and special events at
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.
Live music, comedy, reading club and more at Antoinette's Garden
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
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.
Live Music, Movie Screenings and more at
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 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!
LATRICE CARR AT IL PICCOLO MORSO
PREMIERES: OCTOBER 6, 2021
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.
PHILLIP MICHAEL PARSONS AT OLD TOWNE PUB
PREMIERED: FEBRUARY 14, 2021
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.
PREMIERED: JULY 16, 2021
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!
MARIBETH BOEKE GANZELL
PREMIERES: AUGUST 31, 2021
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.