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Summer smash Events and Things to do in Leonardtown, MD

Summer Nights & Cool Jazz
Sat, Sep 5, 5:00 PM
Maryland · Xella Winery and Vineyard
Summer Nights & Cool Jazz
Sat, Sep 5, 5:00 PM
Maryland · Xella Winery and Vineyard
The Last Crack of Summer - Crabs & Music
Sun, Sep 6, 1:00 PM
Colonial Beach · Circa 1892
The Last Crack of Summer - Crabs & Music
Sun, Sep 6, 1:00 PM
Colonial Beach · Circa 1892
Summer Skin Social
Sat, Sep 19, 2:00 PM
Maryland · Breezy Point Beach & Campground
Summer Skin Social
Sat, Sep 19, 2:00 PM
Maryland · Breezy Point Beach & Campground
Waves & Wellness Retreat‍.
Sun, Sep 13, 2:00 PM
Maryland · Waldorf
Waves & Wellness Retreat‍.
Sun, Sep 13, 2:00 PM
Maryland · Waldorf
Kinusaiga: Black Eyed Susans
Today at 2:00 PM
Maryland · Corteau Vineyards
Kinusaiga: Black Eyed Susans
Today at 2:00 PM
Maryland · Corteau Vineyards
FHS Summer 16 Cookout
Sat, Sep 12, 1:00 PM
North Mount Vernon · Fort Washington Park Area C
FHS Summer 16 Cookout
Sat, Sep 12, 1:00 PM
North Mount Vernon · Fort Washington Park Area C
Second Saturday Family Night
Sat, Sep 12, 5:00 PM
Maryland · Historic Sotterley
Second Saturday Family Night
Sat, Sep 12, 5:00 PM
Maryland · Historic Sotterley
30th Annual Golf Tournament
Fri, Sep 25, 7:30 AM
Maryland · Wicomico Shores Golf Course
30th Annual Golf Tournament
Fri, Sep 25, 7:30 AM
Maryland · Wicomico Shores Golf Course
Lunar Eclipse Paint Night: Light, Release & Renewal
Friday at 6:00 PM
Lusby · 232 Town Square Dr
Lunar Eclipse Paint Night: Light, Release & Renewal
Friday at 6:00 PM
Lusby · 232 Town Square Dr
2nd Annual Health & Wealth Summer Fit Fest
Sat, Aug 29, 9:00 AM
Clinton · Cosca Regional Park Play Area
2nd Annual Health & Wealth Summer Fit Fest
Sat, Aug 29, 9:00 AM
Clinton · Cosca Regional Park Play Area
Paint Nite • Hook & Vine Kitchen and Bar • North Beach
Sun, Aug 30, 3:00 PM
West Beach · Hook & Vine Kitchen and Bar
Paint Nite • Hook & Vine Kitchen and Bar • North Beach
Sun, Aug 30, 3:00 PM
West Beach · Hook & Vine Kitchen and Bar
QueFest 2026
Sat, Sep 19, 12:00 PM
· MartinisLounge
QueFest 2026
Sat, Sep 19, 12:00 PM
· MartinisLounge
2026 Honor the Blue Golf Classic
Mon, Sep 21, 7:30 AM
Lusby · Chesapeake Hills Golf Course
2026 Honor the Blue Golf Classic
Mon, Sep 21, 7:30 AM
Lusby · Chesapeake Hills Golf Course
Spooky Lantern Ceramic Night at WhataBoba Lusby Tea Shop!
Sat, Sep 12, 6:00 PM
Lusby · 232 Town Square Dr
Spooky Lantern Ceramic Night at WhataBoba Lusby Tea Shop!
Sat, Sep 12, 6:00 PM
Lusby · 232 Town Square Dr
Paint and Sip Alzheimer’s Awareness Fund Raiser
Sun, Aug 30, 2:00 PM
Maryland · Corteau Vineyards
Paint and Sip Alzheimer’s Awareness Fund Raiser
Sun, Aug 30, 2:00 PM
Maryland · Corteau Vineyards
The 4 Queens | Tribute to Tina, Aretha, Whitney & Donna
Sun, Sep 13, 2:00 PM
West Beach · The Bandshell at Rod 'N' Reel Resort
The 4 Queens | Tribute to Tina, Aretha, Whitney & Donna
Sun, Sep 13, 2:00 PM
West Beach · The Bandshell at Rod 'N' Reel Resort
THE ULTIMATE SUMMER POOL PARTY EXPERIENCE
Sat, Aug 29, 4:00 PM
Kerby Hill · 201 Waterfront St
THE ULTIMATE SUMMER POOL PARTY EXPERIENCE
Sat, Aug 29, 4:00 PM
Kerby Hill · 201 Waterfront St
CARIBBEAN FOOD, WINE and JAZZ FESTIVAL
Sat, Aug 29, 1:00 PM
Maryland · 27857 Budds Creek Rd
CARIBBEAN FOOD, WINE and JAZZ FESTIVAL
Sat, Aug 29, 1:00 PM
Maryland · 27857 Budds Creek Rd
Spooky Lantern Ceramic Paint Night at WhataBoba Lusby
Fri, Sep 18, 6:00 PM
Lusby · 232 Town Square Dr
Spooky Lantern Ceramic Paint Night at WhataBoba Lusby
Fri, Sep 18, 6:00 PM
Lusby · 232 Town Square Dr
Loveboat Yacht Rock Concert
Sun, Aug 30, 2:00 PM
West Beach · The Bandshell at Rod 'N' Reel Resort
Loveboat Yacht Rock Concert
Sun, Aug 30, 2:00 PM
West Beach · The Bandshell at Rod 'N' Reel Resort

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