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Live Events in Grasonville, Maryland

Grasonville, Maryland has 16 venues with upcoming events — restaurant, gallery and live music venue. 140 events are on the calendar over the next 30 days, at spots like The Jetty, Chesapeake Fine Art Studio, Michael Waskey Music.

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This Weekend in Grasonville

Kent Island Farmer’s Market
Chesapeake Fine Art Studio
Thu, Jul 30 · 3:30 PM
Larry Turner
Kent Island Yacht Club
Thu, Jul 30 · 5:00 PM
Reagan Kent
The Big Owl
Thu, Jul 30 · 6:00 PM
Live Entertainment – Alex Peters
Bridges Restaurant on Kent Narrows
Thu, Jul 30 · 6:00 PM
THURSDAY NIGHT TRIVIA
Chesapeake Fine Art Studio
Thu, Jul 30 · 6:30 PM
4th Thursdays Line Dancing 2026
Chesapeake Fine Art Studio
Thu, Jul 30 · 6:30 PM
Music Bingo & DJ with DJ Juice
The Jetty
Thu, Jul 30 · 7:00 PM
High Tide Grill
Michael Waskey Music
Thu, Jul 30 · 7:00 PM
Live acoustic entertainment
Pour House Pub
Thu, Jul 30 · 7:30 PM
Think N Drink Trivia
Rams Head Shore House
Thu, Jul 30 · 7:30 PM
Friday Avanti Pizza at Love Point Vineyards and Winery
Chesapeake Fine Art Studio
Fri, Jul 31 · 5:00 PM
Kevin Lebling Trio
Kent Island Yacht Club
Fri, Jul 31 · 6:00 PM
Sudlersville Peach Festival
Chesapeake Fine Art Studio
Fri, Jul 31 · 6:00 PM
Live Entertainment – Alli Pinsky
Bridges Restaurant on Kent Narrows
Fri, Jul 31 · 6:00 PM
Sunset Party
The Big Owl
Fri, Jul 31 · 6:00 PM
Crossin' Strings Music
Kent Island Yacht Club
Fri, Jul 31 · 6:00 PM
Par-Tee Time Trivia
Chesapeake Fine Art Studio
Fri, Jul 31 · 6:30 PM
Langways Bar & Grill
Michael Waskey Music
Fri, Jul 31 · 7:00 PM
Shake The Room
The Jetty
Fri, Jul 31 · 8:30 PM
2026 Sudlersville Train Station Museum First Saturdays (and more!) free events!
Chesapeake Fine Art Studio
Sat, Aug 1 · 10:00 AM

Coming Up in Grasonville

Charm City Trivia
The Jetty
Mon, Aug 3 · 7:00 PM
Bingo / Acoustic Duo
The Jetty
Tue, Aug 4 · 6:30 PM
Godfrey’s Silent Book Club – Wednesday Crew
Chesapeake Fine Art Studio
Wed, Aug 5 · 5:00 PM
Music Bingo
Rams Head Shore House
Wed, Aug 5 · 6:00 PM
WINGO
Chesapeake Fine Art Studio
Wed, Aug 5 · 6:00 PM
Joe Bryan
The Big Owl
Wed, Aug 5 · 6:00 PM
Summer Movie Night (The Summer Series)
Kent Island Resort
Wed, Aug 5 · 7:00 PM
Karaoke Night
The Jetty
Wed, Aug 5 · 7:00 PM
Kent Island Farmer’s Market
Chesapeake Fine Art Studio
Thu, Aug 6 · 3:30 PM
Joe Bryan
The Big Owl
Thu, Aug 6 · 6:00 PM
Bridges
Michael Waskey Music
Thu, Aug 6 · 6:00 PM
Cliff Cody
The Big Owl
Thu, Aug 6 · 6:00 PM
THURSDAY NIGHT TRIVIA
Chesapeake Fine Art Studio
Thu, Aug 6 · 6:30 PM
Music Bingo & DJ with DJ Juice
The Jetty
Thu, Aug 6 · 7:00 PM
Live acoustic entertainment
Pour House Pub
Thu, Aug 6 · 7:30 PM
Friday Avanti Pizza at Love Point Vineyards and Winery
Chesapeake Fine Art Studio
Fri, Aug 7 · 5:00 PM
Sunset Party
The Big Owl
Fri, Aug 7 · 6:00 PM
Chef’s Table: Roots and Vine
Kent Island Resort
Fri, Aug 7 · 6:30 PM
Par-Tee Time Trivia
Chesapeake Fine Art Studio
Fri, Aug 7 · 6:30 PM
Mitchner’s Library
Michael Waskey Music
Fri, Aug 7 · 7:00 PM
Starcrush
The Jetty
Fri, Aug 7 · 8:30 PM
Godfrey’s Summer Concert Series featuring Muddy Branch Band
Chesapeake Fine Art Studio
Sat, Aug 8 · 11:00 AM
Bird Daddy Duo
The Big Owl
Sat, Aug 8 · 3:00 PM
Malicious But Delicious - Blue Cat Talk with Jay Fleming
Kent Island Yacht Club
Sat, Aug 8 · 4:00 PM
Prospect Bay Country Club
Michael Waskey Music
Sat, Aug 8 · 6:00 PM
Red Betty & The Ruchus
The Big Owl
Sat, Aug 8 · 7:00 PM
Prisoner’s Cinema and Iron Dahlia LIVE at Cult
Chesapeake Fine Art Studio
Sat, Aug 8 · 7:30 PM
Godfrey’s Silent Book Club – Sunday Crew
Chesapeake Fine Art Studio
Sun, Aug 9 · 9:00 AM
Centreville Farmers’ Market
Chesapeake Fine Art Studio
Sun, Aug 9 · 9:00 AM
Michael Armstrong
The Big Owl
Sun, Aug 9 · 3:00 PM
Edentown Brewing
Michael Waskey Music
Sun, Aug 9 · 3:00 PM
Jude Strawley
The Big Owl
Sun, Aug 9 · 3:00 PM
Charm City Trivia
The Jetty
Mon, Aug 10 · 7:00 PM
Books & Beers 2026
Chesapeake Fine Art Studio
Tue, Aug 11 · 6:00 PM
of the month from
Cult Classic Brewing
Tue, Aug 11 · 6:00 PM
Bingo / Acoustic Duo
The Jetty
Tue, Aug 11 · 6:30 PM
Godfrey’s Silent Book Club – Wednesday Crew
Chesapeake Fine Art Studio
Wed, Aug 12 · 5:00 PM
Music Bingo
Rams Head Shore House
Wed, Aug 12 · 6:00 PM
WINGO
Chesapeake Fine Art Studio
Wed, Aug 12 · 6:00 PM
Karaoke Night
The Jetty
Wed, Aug 12 · 7:00 PM

Venues in Grasonville (16)

The JettyRestaurant
172 events
Chesapeake Fine Art StudioGallery
163 events
Michael Waskey MusicLive Music Venue
55 events
The Big OwlBar & Pub
49 events
Stevensville Arts & EntertainmentGallery
12 events
Stevensville Historic DistrictHistorical place
12 events
Cult Classic BrewingRestaurant
8 events
Kent Island ResortVenue
5 events
Kent Island Yacht ClubBoat club
5 events
Rams Head Shore HouseRestaurant
5 events
Bridges Restaurant on Kent NarrowsRestaurant
3 events
Chesapeake Bay Community BandLive Music Venue
3 events
Pour House PubBar & Pub
2 events
Libbey's Coastal Kitchen and CocktailsRestaurant
1 event
Love Point Vineyards and WineryWinery
1 event
St. Michaels Concours d'Elegance on Chesapeake BayOutdoor Venue
1 event
Live Events in Grasonville, Maryland | Orion's Map