Leonardtown First Fridays

If you’re looking to explore and enjoy Southern Maryland, put Leonardtown on your list. For a small town, this place has a lot of soul and charm and has become a getaway from some of the larger cities in Maryland. It’s also home to Southern Maryland’s only Arts and Entertainment District, which includes 100 acres to peruse while enjoying art galleries, restaurants, and shops. Also located in the center of downtown is the Port of Leonardtown Winery, making this town a must-visit for wine connoisseurs. With such a vibrant community, it’s only fitting that they have special events to celebrate and enjoy all they have to offer. Leonardtown First Fridays take place each month as a celebration of the local art, music, and food culture.

First Fridays

On the first Friday of each month throughout the year (even in the chilly winter months), locals and visitors can enjoy all kinds of free entertainment in historic Leonardtown. The many cafes, bookstores, gift shops, galleries, and restaurants keep their doors open late and host special receptions to enjoy. You can expect to see local artists’ work, live entertainment, and even some interactive activities to get involved in.

Where and when:

This event happens in Leonardtown Square and Leonardtown Shopping Centers on the first Friday of the month from about 5:00-8:00PM. There’s an occasional interactive drum circle which takes place St. Mary’s County Arts Council, at 22660 Washington St., from 8:00-9:00PM as well.

June 7th: Crab Fest Friday

Coming up this Friday night, you can catch Leonardtown’s Crab Fest Friday event. Here are some of the special promotions and entertainment you can expect:


This Friday, they’ll have local trio HydraFX playing a free show for all First Friday visitors to enjoy. Musicians Greg Barrick, Scott Barber, and Derik Rotton make up this trio that will be playing at The Square. They’ve prepared a great show including a blend of both original rock/reggae music as well as some popular covers.


If you’d like to picnic on The Square during all the fun, Leonardtown First Friday is offering an “Order a Picnic” option where you can pre-order dinner to-go from many of the local restaurants. Of course, you can still dine indoors at any of the amazing restaurants in town, many of which will be offering one-evening-only specials.


This month’s First Friday also includes art opening receptions in many galleries for featured artists and their new shows. The art studios and gift shops will be open late so you can wander through from 5:00-8:00PM during the event.

Kids activities:

If you want something the kids can enjoy while you shop and socialize, there’s a Drop N’ Dine option for parents of children between the ages of 5-12. There will be an art project for them to do for up to 3 hours during the First Friday event. Make sure to register ahead to secure your child’s spot.

Drum Circle:

This month, they’re continuing the extended First Friday hours with the SoMar Drummers and the Drum Circle. Catch them at St. Mary’s County Arts Council from 8:00-9:00PM. Visitors can come to listen to the music or participate in the circle themselves with percussion instruments available to borrow.


First Fridays in Leonardtown are one of the best free community events in Southern Maryland. With opportunities to explore local artists, enjoy local performances, and savor the local flavors, it’s a family-friendly celebration of some of Southern Maryland’s best.

Upcoming 2019 First Fridays:

July 5th: Red, White & Blues First Friday

August 2nd: First Responder First Friday

September 6th: ArtWalk First Friday

October 4th, Fall Fest First Friday

November 1st, Día de Los Muertos First Friday

December 6th, Keep the Cheer Here First Friday

Leave a Reply

Your email address will not be published. Required fields are marked *

You may use these HTML tags and attributes: <a href="" title=""> <abbr title=""> <acronym title=""> <b> <blockquote cite=""> <cite> <code> <del datetime=""> <em> <i> <q cite=""> <strike> <strong>