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Events and Things to do in Leonardtown, MD

Search for something you love or check out popular events in your area.

Fresh Wind Roundtable 2026
Waldorf · iNgage Community Church - The Park
Fresh Wind Roundtable 2026
Waldorf · iNgage Community Church - The Park
Mommy & Me Mother's Day Paint Date
Fri, May 8, 5:00 PM + 1 more
La Plata · Joyful Studio
Mommy & Me Mother's Day Paint Date
Fri, May 8, 5:00 PM + 1 more
La Plata · Joyful Studio
Plant Bingo @ Angie’s Boutique
Thu, Apr 23, 6:00 PM
Warsaw · Angie's Strength and Style Boutique
Plant Bingo @ Angie’s Boutique
Thu, Apr 23, 6:00 PM
Warsaw · Angie's Strength and Style Boutique
SUNFLOWER FESTIVAL
Sat, Apr 25, 12:00 PM
Waldorf · Shops at Waldorf Center
SUNFLOWER FESTIVAL
Sat, Apr 25, 12:00 PM
Waldorf · Shops at Waldorf Center
Network, Chew, and Line Dance Experience
Thu, Apr 23, 5:30 PM
Waldorf · 11750 Business Park Dr ste 203
Network, Chew, and Line Dance Experience
Thu, Apr 23, 5:30 PM
Waldorf · 11750 Business Park Dr ste 203
757/804 DAY TRIP TO WALDORF, MD: CUSTOM HAND BAG PARTY
Sat, Jun 20, 9:00 AM
Waldorf · Paint N Sip
757/804 DAY TRIP TO WALDORF, MD: CUSTOM HAND BAG PARTY
Sat, Jun 20, 9:00 AM
Waldorf · Paint N Sip
Conflict Management Certification Training in Bennsville, MD
Fri, Mar 27, 9:00 AM + 19 more
Bennsville · Regus - The venue will be close to your place. It can be conducted near your zip code
Conflict Management Certification Training in Bennsville, MD
Fri, Mar 27, 9:00 AM + 19 more
Bennsville · Regus - The venue will be close to your place. It can be conducted near your zip code
YHWH Launch Night
Fri, Jun 26, 8:00 PM
Waldorf · 2772 Old Washington Rd
YHWH Launch Night
Fri, Jun 26, 8:00 PM
Waldorf · 2772 Old Washington Rd
Shops at Waldorf Center Classic Car Show with DMV Rods & Classic's Car Club
Sat, May 16, 9:00 AM + 2 more
Waldorf · Shops at Waldorf Center
Shops at Waldorf Center Classic Car Show with DMV Rods & Classic's Car Club
Sat, May 16, 9:00 AM + 2 more
Waldorf · Shops at Waldorf Center
Paint and Sip
Sun, Apr 19, 2:00 PM
Port Tobacco · Port Tobacco Restaurant
Paint and Sip
Sun, Apr 19, 2:00 PM
Port Tobacco · Port Tobacco Restaurant
KIM SPRING TAKEOVER
Sat, Apr 25, 9:00 PM
Waldorf · 2056 Crain Hwy
KIM SPRING TAKEOVER
Sat, Apr 25, 9:00 PM
Waldorf · 2056 Crain Hwy
Sales end soon
DCVYBE Live @ Piano Keys Lounge. Every Thursday
Thursday at 7:00 PM + 41 more
Brandywine · Piano Keys Restaurant and Lounge
Sales end soon
DCVYBE Live @ Piano Keys Lounge. Every Thursday
Thursday at 7:00 PM + 41 more
Brandywine · Piano Keys Restaurant and Lounge
3rd Annual All White Soirée
Sat, May 9, 4:00 PM
Brandywine · TBD
3rd Annual All White Soirée
Sat, May 9, 4:00 PM
Brandywine · TBD
The Afternoon Affair: A Brunch & Vendor Social
Sun, May 31, 12:00 PM
Waldorf · The Space by LBI Collective
The Afternoon Affair: A Brunch & Vendor Social
Sun, May 31, 12:00 PM
Waldorf · The Space by LBI Collective
Autumn Dinner '26
Sat, Oct 10, 4:00 PM
Waldorf · 10400 Griffith Ln
Autumn Dinner '26
Sat, Oct 10, 4:00 PM
Waldorf · 10400 Griffith Ln
Friday After Work w/ Secret Society @ Piano Keys Lounge - 1st & 3rd Fri
Fri, Apr 3, 5:00 PM + 3 more
Brandywine · Piano Keys Restaurant and Lounge
Friday After Work w/ Secret Society @ Piano Keys Lounge - 1st & 3rd Fri
Fri, Apr 3, 5:00 PM + 3 more
Brandywine · Piano Keys Restaurant and Lounge
WHAT BAND FT KILLA Performing Live @ Piano Keys Lounge - 1st & 3rd Friday
Friday at 9:00 PM + 8 more
Brandywine · Piano Keys Restaurant and Lounge
WHAT BAND FT KILLA Performing Live @ Piano Keys Lounge - 1st & 3rd Friday
Friday at 9:00 PM + 8 more
Brandywine · Piano Keys Restaurant and Lounge
Foodies + New Friends Tappahannock: Small Business Owners Edition
Mon, Mar 30, 7:00 PM + 18 more
Tappahannock · Restaurant of the Week
Foodies + New Friends Tappahannock: Small Business Owners Edition
Mon, Mar 30, 7:00 PM + 18 more
Tappahannock · Restaurant of the Week
Going fast
Everyday Makeup Routine Makeup Tutorial Class (Calvert County, MD)
Fri, Apr 17, 6:30 PM
Dunkirk · Fresco Studios, LLC
Going fast
Everyday Makeup Routine Makeup Tutorial Class (Calvert County, MD)
Fri, Apr 17, 6:30 PM
Dunkirk · Fresco Studios, LLC
Just added
PTR's 1ST ANNUAL SPRING CAR SHOW
Sat, May 9, 10:00 AM
Port Tobacco · 7536 Shirley Blvd
Just added
PTR's 1ST ANNUAL SPRING CAR SHOW
Sat, May 9, 10:00 AM
Port Tobacco · 7536 Shirley Blvd

Trends in Leonardtown

Explore more trends

Explore more trends

Frequently asked questions about Leonardtown

What are the best events to attend?

According to Eventbrite, the best events are:

Fresh Wind Roundtable 2026

Mommy & Me Mother's Day Paint Date

Plant Bingo @ Angie’s Boutique

SUNFLOWER FESTIVAL

Which events are currently trending in Leonardtown?

The trending searches this month in Leonardtown are:

st marys county maryland

Which events are coming up?

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

DCVYBE Live @ Piano Keys Lounge. Every Thursday

WHAT BAND FT KILLA Performing Live @ Piano Keys Lounge - 1st & 3rd Friday

Conflict Management Certification Training in Bennsville, MD

Foodies + New Friends Tappahannock: Small Business Owners Edition