June 3, 2026

Visit Leonardtown on First Friday

Leonardtown

First Friday opens up Leonardtown, MD, for one-of-a-kind shopping and entertainment, and invites visitors to join in some fun April 3. The theme is “Sip, Shop & Hop.”

Lecture Topic: A Forgotten Patriot

Patriot

David Brown, a retired adjunct professor at Johns Hopkins University, will give a talk at the Historically Speaking event March 26, 2026, at St. Mary’s College of Maryland.

Visit Leonardtown on First Friday

First Friday

First Friday opens up Leonardtown, MD, for one-of-a-kind shopping and entertainment, and invites visitors to join in some fun February 6. The theme is “Love in Leonardtown.”

Leonardtown First Friday Dec. 5

Leonardtown

First Friday Weekends open up Leonardtown, MD, for one-of-a-kind shopping and entertainment, and invite visitors to join in some fun December 5-7. The weekend’s theme is Gingerbread Lane.

Shop & Stroll at First Friday Nov. 7

Shop

First Friday Weekends open up Leonardtown, MD, for one-of-a-kind shopping and entertainment, and invite visitors to join in some fun November 7-8. Take a stroll around town, get your passport stamped at participating businesses, and enter to win prizes.

First Friday in Leonardtown Oct. 3

First Friday Weekends open up Leonardtown, MD, for one-of-a-kind shopping and entertainment, and invite visitors to join in some Octoberfest fun October 3-5. Take the Scarecrow Stroll. Come to town to see the scarecrows displayed all over town and then vote for your favorite.

Historical Society Dinner Set Oct. 24

Barber Family

Save the date for the Historical Society of St. Mary’s 2025 fall dinner at the Olde Breton Inn in Leonardtown. The event will be held October 24.

Leonardtown First Friday Art Walk

First Friday

First Friday Weekends open up Leonardtown, MD, for one-of-a-kind shopping and entertainment, and invite visitors to join in some fun September 5-7. The St. Mary’s County Arts Council and the town are kicking off their annual Art Walk in September.

Historically Speaking Topic: Negotiating Changing Chesapeake Identities

Lecture

Historically Speaking will welcome Valerie Hall and her presentation on Maryland’s indigenous population, especially Indian women, who transformed Early British American society during the 17th century. Ms. Hall will speak from 7 to 9pm Wednesday, August 20, 2025, in Leonardtown.

Leonardtown First Friday Weekend Aug. 1-3

First Friday

First Friday Weekends open up Leonardtown, MD, for one-of-a-kind shopping and entertainment, and invite visitors to join in the fun August 1-3.