Events and Things to do in Leonardtown, MD

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Vendor or Sponsor Registration for Home for The Holidays
Sat, Dec 5, 4:00 PM
Maryland · Saint Mary's Fairgrounds
Vendor or Sponsor Registration for Home for The Holidays
Sat, Dec 5, 4:00 PM
Maryland · Saint Mary's Fairgrounds
Sins And Secrets After Dark
Fri, Oct 30, 8:00 PM
Leonardtown · The Rex
Sins And Secrets After Dark
Fri, Oct 30, 8:00 PM
Leonardtown · The Rex
Boots & BBQ Hoedown
Sat, Nov 7, 4:00 PM
Maryland · Greenwell State Park
Boots & BBQ Hoedown
Sat, Nov 7, 4:00 PM
Maryland · Greenwell State Park
Spooky Solomons Psychic Ghost Tour, Monday, October 26
Mon, Oct 26, 6:00 PM
Maryland · Solomons
Spooky Solomons Psychic Ghost Tour, Monday, October 26
Mon, Oct 26, 6:00 PM
Maryland · Solomons
BKLYN: The Musical at St. Mary's College of Maryland
Thu, Nov 12, 8:00 PM + 4 more
Maryland · Bruce Davis Theater, Montgomery Hall, St. Mary's College of Maryland
BKLYN: The Musical at St. Mary's College of Maryland
Thu, Nov 12, 8:00 PM + 4 more
Maryland · Bruce Davis Theater, Montgomery Hall, St. Mary's College of Maryland
DIG! St. Mary's Fort Excavation Experience (Oct 24)
Sat, Oct 24, 9:00 AM
Maryland · Historic St. Mary's City
DIG! St. Mary's Fort Excavation Experience (Oct 24)
Sat, Oct 24, 9:00 AM
Maryland · Historic St. Mary's City
So MD Smooth Steppaz "Fall In Line" Field Party
Sat, Nov 7, 3:00 PM
Maryland · Knight Life Ball Field (formerly Jolly Gents/Stardust/Kitchen Latrice)
So MD Smooth Steppaz "Fall In Line" Field Party
Sat, Nov 7, 3:00 PM
Maryland · Knight Life Ball Field (formerly Jolly Gents/Stardust/Kitchen Latrice)
Sales end soon
2026 SMCM Women's Basketball Skills & Prospect Camp
Sunday at 9:30 AM
Maryland · St. Mary's College of Maryland
Sales end soon
2026 SMCM Women's Basketball Skills & Prospect Camp
Sunday at 9:30 AM
Maryland · St. Mary's College of Maryland
Sales end soon
Willett Exclusive Release Event
Tuesday at 5:30 PM
Leonardtown · SOCIAL Coffeehouse & Cocktail Bar
Sales end soon
Willett Exclusive Release Event
Tuesday at 5:30 PM
Leonardtown · SOCIAL Coffeehouse & Cocktail Bar
Sotterley Garden Guild Wreath Workshop
Sat, Dec 5, 9:00 AM
Maryland · Historic Sotterley
Sotterley Garden Guild Wreath Workshop
Sat, Dec 5, 9:00 AM
Maryland · Historic Sotterley
Home for The Holidays - A New St. Mary's County Holiday Tradition
Sat, Dec 5, 4:00 PM
Maryland · Saint Mary's Fairgrounds
Home for The Holidays - A New St. Mary's County Holiday Tradition
Sat, Dec 5, 4:00 PM
Maryland · Saint Mary's Fairgrounds
1980s Murder Mystery Dinner
Sat, Oct 24, 6:00 PM
Maryland · Corteau Vineyards
1980s Murder Mystery Dinner
Sat, Oct 24, 6:00 PM
Maryland · Corteau Vineyards
Black Velvet: A Lounge Experience
Fri, Oct 30, 7:00 PM
Leonardtown · 41655 Fenwick St
Black Velvet: A Lounge Experience
Fri, Oct 30, 7:00 PM
Leonardtown · 41655 Fenwick St
Southern Maryland Plant Nerds Presents Halloween Plant Bingo!
Fri, Oct 30, 6:30 PM
Lusby · WhataBoba
Southern Maryland Plant Nerds Presents Halloween Plant Bingo!
Fri, Oct 30, 6:30 PM
Lusby · WhataBoba
Next Stop Comedy at Ice House Brewery! - Colonial Beach, VA
Thu, Dec 31, 8:00 PM + 3 more
Colonial Beach · Ice House Brewery & Kitchen
Next Stop Comedy at Ice House Brewery! - Colonial Beach, VA
Thu, Dec 31, 8:00 PM + 3 more
Colonial Beach · Ice House Brewery & Kitchen
SKYBOX & THE BAAC MEDIA PRESENTS LANEPUSHERS IN MY OWN LANE (MARYLAND)
Sat, Nov 14, 7:00 PM
Leonardtown · 22725 Duke St
SKYBOX & THE BAAC MEDIA PRESENTS LANEPUSHERS IN MY OWN LANE (MARYLAND)
Sat, Nov 14, 7:00 PM
Leonardtown · 22725 Duke St
Beyond the Guidebook: An Oracle Card Workshop - Friday, November 13
Fri, Nov 13, 5:00 PM
Lusby · WhataBoba
Beyond the Guidebook: An Oracle Card Workshop - Friday, November 13
Fri, Nov 13, 5:00 PM
Lusby · WhataBoba
LEGO Building Day
Sun, Nov 8, 2:00 PM
Maryland · Corteau Vineyards
LEGO Building Day
Sun, Nov 8, 2:00 PM
Maryland · Corteau Vineyards
Holiday Designer Purse Bingo
Sun, Dec 6, 12:30 PM
Mechanicsville · Mechanicsville VFD
Holiday Designer Purse Bingo
Sun, Dec 6, 12:30 PM
Mechanicsville · Mechanicsville VFD
Sales end soon
Paint and Sip Mason Jar Lights
Sunday at 2:00 PM
Maryland · Corteau Vineyards
Sales end soon
Paint and Sip Mason Jar Lights
Sunday at 2:00 PM
Maryland · Corteau Vineyards

Trends in Leonardtown

Explore more trends

Frequently asked questions about Leonardtown

What are the best events to attend?

According to Eventbrite, the best events are:

Vendor or Sponsor Registration for Home for The Holidays

Sins And Secrets After Dark

Boots & BBQ Hoedown

Spooky Solomons Psychic Ghost Tour, Monday, October 26

Which events are currently trending in Leonardtown?

The trending searches this month in Leonardtown are:

car shows

st marys county maryland

mothers day

Which events are coming up?

Discover the best events happening soon – you don't want to miss them:

2026 SMCM Women's Basketball Skills & Prospect Camp

Paint and Sip Mason Jar Lights

Willett Exclusive Release Event

DIG! St. Mary's Fort Excavation Experience (Oct 24)

Vendor or Sponsor Registration for Home for The Holidays

Vendor or Sponsor Registration for Home for The Holidays

Sins And Secrets After Dark

Sins And Secrets After Dark

Boots & BBQ Hoedown

Boots & BBQ Hoedown

Spooky Solomons Psychic Ghost Tour, Monday, October 26

Spooky Solomons Psychic Ghost Tour, Monday, October 26

BKLYN: The Musical at St. Mary's College of Maryland

BKLYN: The Musical at St. Mary's College of Maryland

DIG! St. Mary's Fort Excavation Experience (Oct 24)

DIG! St. Mary's Fort Excavation Experience (Oct 24)

So MD Smooth Steppaz "Fall In Line" Field Party

So MD Smooth Steppaz "Fall In Line" Field Party

2026 SMCM Women's Basketball Skills & Prospect Camp

2026 SMCM Women's Basketball Skills & Prospect Camp

Willett Exclusive Release Event

Willett Exclusive Release Event

Sotterley Garden Guild Wreath Workshop

Sotterley Garden Guild Wreath Workshop

Home for The Holidays - A New St. Mary's County Holiday Tradition

Home for The Holidays - A New St. Mary's County Holiday Tradition

1980s Murder Mystery Dinner

1980s Murder Mystery Dinner

Black Velvet: A Lounge Experience

Black Velvet: A Lounge Experience

Southern Maryland Plant Nerds Presents Halloween Plant Bingo!

Southern Maryland Plant Nerds Presents Halloween Plant Bingo!

Next Stop Comedy at Ice House Brewery! - Colonial Beach, VA

Next Stop Comedy at Ice House Brewery! - Colonial Beach, VA

SKYBOX & THE BAAC MEDIA PRESENTS LANEPUSHERS IN MY OWN LANE (MARYLAND)

SKYBOX & THE BAAC MEDIA PRESENTS LANEPUSHERS IN MY OWN LANE (MARYLAND)

Beyond the Guidebook: An Oracle Card Workshop - Friday, November 13

Beyond the Guidebook: An Oracle Card Workshop - Friday, November 13

LEGO Building Day

LEGO Building Day

Holiday Designer Purse Bingo

Holiday Designer Purse Bingo

Paint and Sip Mason Jar Lights

Paint and Sip Mason Jar Lights

Things to do around Leonardtown

Trends in Leonardtown

1. Car shows

2. St marys county maryland

3. Mothers day

4. 5k

5. Free kids events

6. St mary's county maryland

7. Line dancing

8. Yung joc

9. Summer smash

10. Singles

11. Plant bingo

12. Sound bath

What are the best events to attend?

Which events are currently trending in Leonardtown?

Which events are coming up?