Join us year-round every First Friday of the month from 5 to 8 pm for an evening of fun entertainment, unique shopping and various dining options!
 

On the first Friday of every month, historic Leonardtown's art galleries, restaurants, cafes, gift shops, antique shops, bookstores, etc. open their doors to showcase local artists and/or serve specials at their establishments.

You are invited to a fun evening of live entertainment, artistic demos, receptions, hands-on activities, and seasonal promotions. New this year, Leonardtown First Fridays are being expanded to Leonardtown First Friday All Weekend Events starting in May and continuing through October. See the upcoming event themes below!
 

First Friday All Weekend Event Themes:

MAY

Mad About Leonardtown First Friday All Weekend Extravaganza












Come to Leonardtown the weekend of May 6 - 8, 2022 to join in a unique experience that will both thrill and delight! In honor of the completion of Leonardtown’s latest, most unique mural titled “Alice in Leonardtown”, the Town will throw a three-day spectacular featuring a CURIOUSER and CURIOUSER Cocktail Party and fundraiser, the mural ribbon cutting, a FREE A&E Movie Festival, a popup art show and more! Learn More








 

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JUNE
Celebrating St. Mary's First Friday All Weekend Event






 

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More info to come...
 

JULY
The Jazzy First Friday All Weekend Celebration








Leonardtown is starting the Jazz Festival celebration early with the Jazzy First Friday All Weekend Celebration in honor of the Potomac Jazz & Seafood Festival Three-Day Weekend Celebration that will take place July 8th -10th.
Enjoy jazz related events and activities throughout Leonardtown. Learn More About the Jazz Festival
 

AUGUST
Dog Days of Summer First Friday All Weekend Celebration





 

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Pet events and special offers with the Leonardtown businesses. More info to come.

 

SEPTEMBER

A&E/Art Walk First Friday All Weekend Celebration







 

Enjoy live music from the Higher Standards jazz trio and art activities (TBA) all around Leonardtown in honor of the Anniversary of Leonardtown's designation as an Arts & Entertainment District. More info to come

 

OCTOBER

Fall Fest First Friday All Weekend Celebration







 

Participate in the Annual Scarecrow Stroll and vote for the business with your favorite scarecrow. Also, this weekend Brudergarten at Shepherd's Old Field Market will host the 2nd Annual Octoberfest event (more info is forthcoming).

First Friday is a year-round event which is sponsored by the Leonardtown Business Association

First Friday Itinerary

First Friday Specials