Events & Entertainment

Upcoming Events

Gallery Shows at North End Gallery

Enjoy great themed gallery shows each month from the incredible artists at North End Gallery in Leonardtown.

Little Explorers at Historic St. Mary’s City

Family-friendly event designed for preschool-age children 3-5 years old and an accompanying adult. Full-day admission included in cost. Different theme each time.

Gallery Shows at North End Gallery

Enjoy great themed gallery shows each month from the incredible artists at North End Gallery in Leonardtown.

Gallery Shows at North End Gallery

Enjoy great themed gallery shows each month from the incredible artists at North End Gallery in Leonardtown.

Gallery Shows at North End Gallery

Enjoy great themed gallery shows each month from the incredible artists at North End Gallery in Leonardtown.

Leonardtown First Fridays

The First Friday of each month, historic Leonardtown retailers open their doors to showcase live music,… more

Music at the Winery

Chill with the live tunes of local artists at the winery each Saturday while sipping on award winning wines.

Open Barn at Greenwell State Park

Every Saturday morning, meet with Greenwell's horses, watch riding lessons, and learn about the Greenwell Foundation's equestrian programs. FREE.

Saturday Sidewalk Sale at Tulagi Place

Support your community and local businesses by coming out to the monthly Saturday Sidewalk Sale at Tulagi Place, Lexington Park, Maryland.

Annual Youth Fishing Rodeo

Fun "Catch and Release" fishing event, rain or shine, for children ages 15 and younger. Free. Registration Required.

Gallery Shows at North End Gallery

Enjoy great themed gallery shows each month from the incredible artists at North End Gallery in Leonardtown.

Music at the Winery

Chill with the live tunes of local artists at the winery each Saturday while sipping on award winning wines.

Gallery Shows at North End Gallery

Enjoy great themed gallery shows each month from the incredible artists at North End Gallery in Leonardtown.

Gallery Shows at North End Gallery

Enjoy great themed gallery shows each month from the incredible artists at North End Gallery in Leonardtown.

Gallery Shows at North End Gallery

Enjoy great themed gallery shows each month from the incredible artists at North End Gallery in Leonardtown.

Gallery Shows at North End Gallery

Enjoy great themed gallery shows each month from the incredible artists at North End Gallery in Leonardtown.

Open Barn at Greenwell State Park

Every Saturday morning, meet with Greenwell's horses, watch riding lessons, and learn about the Greenwell Foundation's equestrian programs. FREE.

Gallery Shows at North End Gallery

Enjoy great themed gallery shows each month from the incredible artists at North End Gallery in Leonardtown.

Music at the Winery

Chill with the live tunes of local artists at the winery each Saturday while sipping on award winning wines.

Gallery Shows at North End Gallery

Enjoy great themed gallery shows each month from the incredible artists at North End Gallery in Leonardtown.

Little Explorers at Historic St. Mary’s City

Family-friendly event designed for preschool-age children 3-5 years old and an accompanying adult. Full-day admission included in cost. Different theme each time.

Gallery Shows at North End Gallery

Enjoy great themed gallery shows each month from the incredible artists at North End Gallery in Leonardtown.