Visit St. Mary's County Maryland

Where the Potomac & the Chesapeake meet

Festivals & Events

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

Sep 19 Thu

Sep 19 Thu

Visitor Favorite

September 19 @ 4:00 PM
( September 19–22 )

St. Mary’s County Fair

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

(301) 475-2256

Festivals & Events | Farm Fun | Just For Kids | Food & Wine | Fairs & Festivals | History, Heritage & Folk Life | Leonardtown Events | Lectures & Programs

Sep 20 Fri

Sep 20 Fri

Visitor Favorite

September 20 @ 9:00 AM
( September 19–22 )

St. Mary’s County Fair

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

(301) 475-2256

Festivals & Events | Farm Fun | Just For Kids | Food & Wine | Fairs & Festivals | History, Heritage & Folk Life | Leonardtown Events | Lectures & Programs

Sep 21 Sat

Sep 21 Sat

September 21 @ 8:00 AM
( September 21–22 )

Maryland Lighthouse Challenge

Piney Point Lighthouse Museum, Point Lookout Lighthouse, St. Clement's Island
See website for Addresses, Piney Point, MD

38.14258 -76.50849

(410) 397-3743

Festivals & Events | History, Heritage & Folk Life

Sep 21 Sat

Sep 21 Sat

Visitor Favorite

September 21 @ 9:00 AM
( September 19–22 )

St. Mary’s County Fair

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

(301) 475-2256

Festivals & Events | Farm Fun | Just For Kids | Food & Wine | Fairs & Festivals | History, Heritage & Folk Life | Leonardtown Events | Lectures & Programs

Sep 21 Sat

Sep 21 Sat

September 21 @ 10:00 AM

Militia Muster @ Historic St. Mary’s City

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

(240) 895-4990

Festivals & Events | History, Heritage & Folk Life | Lectures & Programs

Sep 22 Sun

Sep 22 Sun

September 22 @ 8:00 AM
( September 21–22 )

Maryland Lighthouse Challenge

Piney Point Lighthouse Museum, Point Lookout Lighthouse, St. Clement's Island
See website for Addresses, Piney Point, MD

38.14258 -76.50849

(410) 397-3743

Festivals & Events | History, Heritage & Folk Life

Sep 22 Sun

Sep 22 Sun

Visitor Favorite

September 22 @ 9:00 AM
( September 19–22 )

St. Mary’s County Fair

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

(301) 475-2256

Festivals & Events | Farm Fun | Just For Kids | Food & Wine | Fairs & Festivals | History, Heritage & Folk Life | Leonardtown Events | Lectures & Programs

Sep 28 Sat

Sep 28 Sat

September 28 @ 10:00 AM

The Artillery of Point Lookout

Point Lookout State Park
11175 Point Lookout Road, Scotland, MD 20687

(301) 872-5688

Festivals & Events | History, Heritage & Folk Life | Sports & Recreation

Sep 28 Sat

Sep 28 Sat

September 28 @ 9:00 AM
( Apr. 20 – Oct. 12 )

Coastal Arts Market at the Wharf

22550 Washington Street, Leonardtown, MD 20650

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

Sep 28 Sat

Sep 28 Sat

Visitor Favorite

September 28 @ 11:00 AM

RetroFest on the Potomac

Piney Point Lighthouse Museum & Historic Park
44720 Lighthouse Road, Piney Point, MD 20674

(301) 994-1471

Festivals & Events | Food & Wine | Fairs & Festivals | History, Heritage & Folk Life

Sep 28 Sat

Sep 28 Sat

September 28 @ 12:00 PM

2019 Harvest Festival and Grape Stomp

Port of Leonardtown Winery
23190 Newtowne Neck Rd, Leonardtown, MD 20650

(301) 690-2192

Sep 29 Sun

Sep 29 Sun

September 28 @ 10:00 AM

The Artillery of Point Lookout

Point Lookout State Park
11175 Point Lookout Road, Scotland, MD 20687

(301) 872-5688

Festivals & Events | History, Heritage & Folk Life | Sports & Recreation

Oct 4 Fri

Oct 4 Fri

October 4 @ 5:00 PM
( Jun. 7 – Mar. 6 )

Leonardtown First Friday’s

Leonardtown Square and Leonardtown Shopping Centers
Leonardtown, MD 20650

(301) 475-9791

Festivals & Events | Leonardtown Events

Oct 4 Fri

Oct 4 Fri

October 4 @ 7:00 PM
( Jul. 5 – Apr. 3 )

Audience Participation Drum Circle

St. Mary's Art Council
22660 Washington St, Leonardtown, MD 20650

(240) 309-4061

Festivals & Events | Leonardtown Events | Music, Theater, Arts

Oct 5 Sat

Oct 5 Sat

Visitor Favorite

October 5
( October 5–6 )

Blessing of the Fleet

St. Clement's Island Museum
38370 Point Breeze Road, Coltons Point, MD 20626

38.22593 -76.75100

(301) 481-2801

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

Oct 5 Sat

Oct 5 Sat

October 5 @ 10:00 AM
( October 5–6 )

“The Soldiers of Point Lookout/St. Mary’s County” Timeline Event

Point Lookout State Park
11175 Point Lookout Road, Scotland, MD 20687

(301) 872-5688

Festivals & Events | History, Heritage & Folk Life

Oct 5 Sat

Oct 5 Sat

October 5 @ 11:00 AM
( Aug. 3 – Oct. 5 )

Drayden African American Schoolhouse Open House

Drayden African American Schoolhouse
18287 Cherryfield Road, Drayden, MD 20630

(301) 994-1471

Festivals & Events | History, Heritage & Folk Life

Oct 5 Sat

Oct 5 Sat

Visitor Favorite

October 5 @ 12:00 PM
( October 5–6 )

Riverside WineFest at Sotterley Plantation

44300 Sotterley Lane, Hollywood, MD 20636

(301) 373-2280

Festivals & Events | Food & Wine | Fairs & Festivals | History, Heritage & Folk Life | Music, Theater, Arts

Oct 6 Sun

Oct 6 Sun

Visitor Favorite

October 6
( October 5–6 )

Blessing of the Fleet

St. Clement's Island Museum
38370 Point Breeze Road, Coltons Point, MD 20626

38.22593 -76.75100

(301) 481-2801

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

Oct 6 Sun

Oct 6 Sun

October 6 @ 10:00 AM
( October 5–6 )

“The Soldiers of Point Lookout/St. Mary’s County” Timeline Event

Point Lookout State Park
11175 Point Lookout Road, Scotland, MD 20687

(301) 872-5688

Festivals & Events | History, Heritage & Folk Life

Oct 6 Sun

Oct 6 Sun

Visitor Favorite

October 6 @ 12:00 PM
( October 5–6 )

Riverside WineFest at Sotterley Plantation

44300 Sotterley Lane, Hollywood, MD 20636

(301) 373-2280

Festivals & Events | Food & Wine | Fairs & Festivals | History, Heritage & Folk Life | Music, Theater, Arts

Visit St. Mary's MD
23115 Leonard Hall Dr.
P.O. Box 653
Leonardtown, MD 20650

main1-800-327-9023

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