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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.

Sales end soon
Suttle Thoughts Live @ Piano Keys Lounge - Every 4th Friday
Friday at 9:30 PM + 5 more
Brandywine · Piano Keys Restaurant and Lounge
Sales end soon
Suttle Thoughts Live @ Piano Keys Lounge - Every 4th Friday
Friday at 9:30 PM + 5 more
Brandywine · Piano Keys Restaurant and Lounge
Sales end soon
Tickle Me Tuesday w/ Mike Brooks & Friends @ Piano Keys 1st & 3rd Tuesday
Today at 6:00 PM + 6 more
Brandywine · Piano Keys Restaurant and Lounge
Sales end soon
Tickle Me Tuesday w/ Mike Brooks & Friends @ Piano Keys 1st & 3rd Tuesday
Today at 6:00 PM + 6 more
Brandywine · Piano Keys Restaurant and Lounge
Sales end soon
The Davis Project Band @ Piano Keys Lounge - 2nd & 4th Friday
Friday at 5:00 PM
Brandywine · Piano Keys Restaurant and Lounge
Sales end soon
The Davis Project Band @ Piano Keys Lounge - 2nd & 4th Friday
Friday at 5:00 PM
Brandywine · Piano Keys Restaurant and Lounge
Sales end soon
Line-Dancing Night Wednesdays @ Piano Keys Restaurant & Lounge Every Wed
Tomorrow at 5:00 PM + 32 more
Brandywine · Piano Keys Restaurant and Lounge
Sales end soon
Line-Dancing Night Wednesdays @ Piano Keys Restaurant & Lounge Every Wed
Tomorrow at 5:00 PM + 32 more
Brandywine · Piano Keys Restaurant and Lounge
Sales end soon
Saturday Night Live Presented by Piano Keys Lounge & WPGC 95.5
Saturday at 9:00 PM + 31 more
Brandywine · Piano Keys Restaurant and Lounge
Sales end soon
Saturday Night Live Presented by Piano Keys Lounge & WPGC 95.5
Saturday at 9:00 PM + 31 more
Brandywine · Piano Keys Restaurant and Lounge
Tuesday Open Mic Karaoke @ Piano Keys Lounge /w D j Big John 2nd & 4th Tue
Tue, May 26, 6:00 PM + 5 more
Brandywine · Piano Keys Restaurant and Lounge
Tuesday Open Mic Karaoke @ Piano Keys Lounge /w D j Big John 2nd & 4th Tue
Tue, May 26, 6:00 PM + 5 more
Brandywine · Piano Keys Restaurant and Lounge
STILL FAMILIAR SUNDAY NIGHT TAKEOVER @ Piano Keys Lounge - Sunday May 31st
Sun, May 31, 7:00 PM
Brandywine · Piano Keys Restaurant and Lounge
STILL FAMILIAR SUNDAY NIGHT TAKEOVER @ Piano Keys Lounge - Sunday May 31st
Sun, May 31, 7:00 PM
Brandywine · Piano Keys Restaurant and Lounge
Blackwater Public Paddle/Taylor's Is. - 2026 - Sultana Education Foundation
Sat, Jun 6, 10:00 AM
Cambridge · Blackwater NWR
Blackwater Public Paddle/Taylor's Is. - 2026 - Sultana Education Foundation
Sat, Jun 6, 10:00 AM
Cambridge · Blackwater NWR
New Impressionz Sunday Funday @ Piano Keys Lounge 1st & 3rd Sunday
Sun, Jun 7, 9:00 PM + 8 more
Brandywine · Piano Keys Restaurant and Lounge
New Impressionz Sunday Funday @ Piano Keys Lounge 1st & 3rd Sunday
Sun, Jun 7, 9:00 PM + 8 more
Brandywine · Piano Keys Restaurant and Lounge
21ST ANNUAL DMV & BEYOND CAR, MOTORCYCLE, & TRUCK CRUISE-IN!
Sat, Jun 6, 2:00 PM
Lothian · Geno's Ball Park
21ST ANNUAL DMV & BEYOND CAR, MOTORCYCLE, & TRUCK CRUISE-IN!
Sat, Jun 6, 2:00 PM
Lothian · Geno's Ball Park
Beloved Keystone Cigar Soiree
Sat, Jun 20, 6:00 PM
Accokeek · Roscoe C Cartwright 129
Beloved Keystone Cigar Soiree
Sat, Jun 20, 6:00 PM
Accokeek · Roscoe C Cartwright 129
Prayer In The Park 2026
Sat, Jul 25, 1:30 PM
Clinton · 3313 Strawberry Hill Dr
Prayer In The Park 2026
Sat, Jul 25, 1:30 PM
Clinton · 3313 Strawberry Hill Dr
Stars, Stripes & Second Chances Dinner & Dance
Sat, Jul 25, 6:00 PM
Deale · Deale Elks Lodge #2528
Stars, Stripes & Second Chances Dinner & Dance
Sat, Jul 25, 6:00 PM
Deale · Deale Elks Lodge #2528
Almost full
LOTUS 50+ LAWN PARTY
Sat, Jun 27, 1:00 PM
Indian Head · Village Green Park
Almost full
LOTUS 50+ LAWN PARTY
Sat, Jun 27, 1:00 PM
Indian Head · Village Green Park
Embers of Excellence Awards and Luncheon
Sat, May 30, 1:00 PM
Nanjemoy · The Amara Retreat
Embers of Excellence Awards and Luncheon
Sat, May 30, 1:00 PM
Nanjemoy · The Amara Retreat
Southern Maryland Archers (SMA) - Try Archery 2026
Sat, Jun 6, 2:00 PM + 1 more
Upper Marlboro · Southern Maryland Archers (SMA) Club
Southern Maryland Archers (SMA) - Try Archery 2026
Sat, Jun 6, 2:00 PM + 1 more
Upper Marlboro · Southern Maryland Archers (SMA) Club
Swing Fore Umoja - The First Annual Foreman Properties Charity Golf Classic
Fri, Jun 19, 9:00 AM
Fort Washington · National Golf Club
Swing Fore Umoja - The First Annual Foreman Properties Charity Golf Classic
Fri, Jun 19, 9:00 AM
Fort Washington · National Golf Club
Slippery When Wet 4.0: Day Party
Sat, Jul 18, 12:00 PM
Upper Marlboro · The Morgan Experience
Slippery When Wet 4.0: Day Party
Sat, Jul 18, 12:00 PM
Upper Marlboro · The Morgan Experience
Slippery When Wet 4.0: Evening Edition
Sat, Jul 18, 5:30 PM
Upper Marlboro · The Morgan Experience
Slippery When Wet 4.0: Evening Edition
Sat, Jul 18, 5:30 PM
Upper Marlboro · The Morgan Experience
Fashion Week Eastern Shore
Sun, Jun 7, 3:30 PM
Cambridge · 108 Chesapeake St
Fashion Week Eastern Shore
Sun, Jun 7, 3:30 PM
Cambridge · 108 Chesapeake St

Trends in Leonardtown

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Frequently asked questions about Leonardtown

What are the best events to attend?

According to Eventbrite, the best events are:

Saturday Night Live Presented by Piano Keys Lounge & WPGC 95.5

Tuesday Open Mic Karaoke @ Piano Keys Lounge /w D j Big John 2nd & 4th Tue

STILL FAMILIAR SUNDAY NIGHT TAKEOVER @ Piano Keys Lounge - Sunday May 31st

Blackwater Public Paddle/Taylor's Is. - 2026 - Sultana Education Foundation

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:

Tickle Me Tuesday w/ Mike Brooks & Friends @ Piano Keys 1st & 3rd Tuesday

Line-Dancing Night Wednesdays @ Piano Keys Restaurant & Lounge Every Wed

The Davis Project Band @ Piano Keys Lounge - 2nd & 4th Friday

Suttle Thoughts Live @ Piano Keys Lounge - Every 4th Friday