Festivals & Events

St. Mary's County is known for tons of signature events! Browse upcoming events below.

Apr 23 Sun

Apr 23 Sun

April 23 @ 8:00 AM
( Apr. 22 – Dec. 10 )

Vintage Source Weekend

22080 Newtowne Neck Road, Compton, MD 20627

38.27435 -76.69421

Festivals and Events | History, Heritage & Folk Life | Leonardtown Events | Music, Theater, Arts

Apr 23 Sun

Apr 23 Sun

April 23 @ 9:00 AM
( April 21–23 )

IDBL Spring Nationals

27861 Budds Creek Road, Mechanicsville, MD 20659

(301) 884-9833

Festivals and Events | Sports & Recreation

Apr 23 Sun

Apr 23 Sun

Visitor Favorite

April 23 @ 12:30 PM

Earth Day on the Square

Leonardtown Square and Leonardtown Wharf Park
22735 Washington Street, Leonardtown, MD 20650

38.29202 -76.63642

(301) 475-9791

Festivals and Events | Fairs & Festivals | Leonardtown Events

Apr 26 Wed

Apr 26 Wed

April 26 @ 6:00 PM
( Mar. 29 – May. 14 )

Gretchen Richie Jazz Cabaret

Ruddy Duck Seafood & Alehouse / The Cow & the Fish
Piney Point, MD

38.14258 -76.50849

(301) 475-2128

Festivals and Events | Food & Wine | Leonardtown Events | Music, Theater, Arts

Apr 29 Sat

Apr 29 Sat

April 29 @ 9:00 AM
( Apr. 1 – Dec. 2 )

Open Barn at Greenwell State Park

25420 Rosedale Manor Lane, Hollywood, MD 20636

(301) 373-9775

Festivals and Events | Farm Fun | Sports & Recreation | Lectures & Programs | Just For Kids

Apr 29 Sat

Apr 29 Sat

April 29 @ 9:00 AM
( April 29–30 )

Garden Guild Plant Sale

44300 Sotterley Lane, Hollywood, MD 20636

(301) 373-2280

Festivals and Events | History, Heritage & Folk Life

Apr 30 Sun

Apr 30 Sun

April 30 @ 8:00 AM

St. Mary’s Historic Half Marathon

Visitor Center, St. Mary’s City, MD 20686

Festivals and Events | Sports & Recreation

Apr 30 Sun

Apr 30 Sun

Visitor Favorite

April 30 @ 8:00 AM

Spring Fling Car Show

Leonardtown Square
22735 Washington Street, Leonardtown, MD 20650

38.29202 -76.63642

(301) 994-9666

Festivals and Events | Fairs & Festivals | Leonardtown Events | Sports & Recreation

Apr 30 Sun

Apr 30 Sun

April 30 @ 11:00 AM
( Mar. 29 – May. 14 )

Gretchen Richie Jazz Cabaret

Ruddy Duck Seafood & Alehouse / The Cow & the Fish
Piney Point, MD

38.14258 -76.50849

(301) 475-2128

Festivals and Events | Food & Wine | Leonardtown Events | Music, Theater, Arts

Apr 30 Sun

Apr 30 Sun

April 30 @ 12:00 PM
( April 29–30 )

Garden Guild Plant Sale

44300 Sotterley Lane, Hollywood, MD 20636

(301) 373-2280

Festivals and Events | History, Heritage & Folk Life

May 3 Wed

May 3 Wed

May 3 @ 10:00 AM
( Apr. 19 – May. 17 )

Little Explorers at Historic St. Mary’s City

Visitor Center, St. Mary’s City, MD 20686

(240) 895-4990

Festivals and Events | History, Heritage & Folk Life | Lectures & Programs | Just For Kids

May 4 Thu

May 4 Thu

May 4 @ 5:00 PM
( May 4–7 )

Southern Maryland Spring Festival

St. Mary’s County Fairgrounds
42455 Fairgrounds Road, Leonardtown, MD 20650

(301) 994-0525

Festivals and Events | Food & Wine | Fairs & Festivals | Leonardtown Events | Lectures & Programs | Just For Kids

May 5 Fri

May 5 Fri

May 5 @ 9:00 AM
( May 5–7 )

Door Wars at Maryland International Raceway

27861 Budds Creek Road, Mechanicsville, MD 20659

(301) 884-9833

Festivals and Events | Sports & Recreation

May 5 Fri

May 5 Fri

May 5 @ 5:00 PM
( May. 5 – Dec. 1 )

Leonardtown First Fridays

Leonardtown Square and Leonardtown Shopping Centers
Leonardtown, MD 20650

38.29089 -76.63592

(301) 475-9791

Festivals and Events | Food & Wine | Fairs & Festivals | History, Heritage & Folk Life | Leonardtown Events | Lectures & Programs | Just For Kids | Music, Theater, Arts

May 5 Fri

May 5 Fri

May 5 @ 5:00 PM
( May 4–7 )

Southern Maryland Spring Festival

St. Mary’s County Fairgrounds
42455 Fairgrounds Road, Leonardtown, MD 20650

(301) 994-0525

Festivals and Events | Food & Wine | Fairs & Festivals | Leonardtown Events | Lectures & Programs | Just For Kids

May 6 Sat

May 6 Sat

May 6 @ 9:00 AM
( Apr. 1 – Dec. 2 )

Open Barn at Greenwell State Park

25420 Rosedale Manor Lane, Hollywood, MD 20636

(301) 373-9775

Festivals and Events | Farm Fun | Sports & Recreation | Lectures & Programs | Just For Kids

May 6 Sat

May 6 Sat

May 6 @ 9:00 AM
( May 5–7 )

Door Wars at Maryland International Raceway

27861 Budds Creek Road, Mechanicsville, MD 20659

(301) 884-9833

Festivals and Events | Sports & Recreation

May 6 Sat

May 6 Sat

May 6 @ 10:00 AM
( May. 6 – Nov. 4 )

Point Lookout State Park Lighthouse Open House

Point Lookout Lighthouse
11175 Point Lookout Road, Scotland, MD 20687

38.05012 -76.32213

(301) 872-5688

Festivals and Events | History, Heritage & Folk Life

May 6 Sat

May 6 Sat

May 6 @ 10:00 AM

May Day at Historic St. Mary’s City

Visitor Center, St. Mary’s City, MD 20686

(240) 895-4990

Festivals and Events | History, Heritage & Folk Life | Lectures & Programs | Just For Kids

May 6 Sat

May 6 Sat

May 6 @ 10:00 AM
( May 4–7 )

Southern Maryland Spring Festival

St. Mary’s County Fairgrounds
42455 Fairgrounds Road, Leonardtown, MD 20650

(301) 994-0525

Festivals and Events | Food & Wine | Fairs & Festivals | Leonardtown Events | Lectures & Programs | Just For Kids