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June Events and Things to do in Annapolis, MD

DMV R&B Wine Festival
Sat, Jun 20, 1:00 PM
Crownsville · Anne Arundel County Fairgrounds
DMV R&B Wine Festival
Sat, Jun 20, 1:00 PM
Crownsville · Anne Arundel County Fairgrounds
American Voices United Through Song - June 6, 2026
Sat, Jun 6, 7:30 PM
Annapolis · Maryland Hall
American Voices United Through Song - June 6, 2026
Sat, Jun 6, 7:30 PM
Annapolis · Maryland Hall
PT. 2 ON THE WATER
Sun, Jun 14, 4:00 PM
Pasadena · Kurtz's Beach Ltd
PT. 2 ON THE WATER
Sun, Jun 14, 4:00 PM
Pasadena · Kurtz's Beach Ltd
Afro - Soca Wine Music & Food Festival
Sun, Jun 21, 1:00 PM
Crownsville · Anne Arundel County Fairgrounds
Afro - Soca Wine Music & Food Festival
Sun, Jun 21, 1:00 PM
Crownsville · Anne Arundel County Fairgrounds
Josh Wallace 2nd Annual Youth Football Camp
Sat, Jun 27, 9:00 AM
Bowie · Whitemarsh Park
Josh Wallace 2nd Annual Youth Football Camp
Sat, Jun 27, 9:00 AM
Bowie · Whitemarsh Park
Rock the Dock
Thu, Jun 4, 6:00 PM
Annapolis · Annapolis Maritime Museum & Park
Rock the Dock
Thu, Jun 4, 6:00 PM
Annapolis · Annapolis Maritime Museum & Park
Going fast
In-person Lactation Basics - AAMC Annapolis, MD
Wed, Jun 17, 5:00 PM
Annapolis · 2000 Medical Pkwy
Going fast
In-person Lactation Basics - AAMC Annapolis, MD
Wed, Jun 17, 5:00 PM
Annapolis · 2000 Medical Pkwy
4th Annual Poodles & Ice Skate Jam
Tue, Jun 9, 7:00 PM
Odenton · Skate Zone Odenton
4th Annual Poodles & Ice Skate Jam
Tue, Jun 9, 7:00 PM
Odenton · Skate Zone Odenton
@@CANCELLED@@ The Hip Hop R&B Yacht Party Annapolis MD 6.7.2026
Sun, Jun 7, 4:45 PM
Annapolis · Annapolis City Dock
@@CANCELLED@@ The Hip Hop R&B Yacht Party Annapolis MD 6.7.2026
Sun, Jun 7, 4:45 PM
Annapolis · Annapolis City Dock
Almost full
DMV R&B Wine Festival Vendor Sign Up
Sat, Jun 20, 1:00 PM
Crownsville · Anne Arundel County Fairgrounds
Almost full
DMV R&B Wine Festival Vendor Sign Up
Sat, Jun 20, 1:00 PM
Crownsville · Anne Arundel County Fairgrounds
Baltimore Speed Dating for Singles Age 35-50 ♥ Maryland at The Greene Turtle - Gambrills
Sun, Jun 14, 3:00 PM
Gambrills · The Greene Turtle - Gambrills
Baltimore Speed Dating for Singles Age 35-50 ♥ Maryland at The Greene Turtle - Gambrills
Sun, Jun 14, 3:00 PM
Gambrills · The Greene Turtle - Gambrills
Dad Games Father's Day Fishing Derby and Brunch
Sat, Jun 6, 6:30 AM
Grasonville · 202 Wells Cove Rd
Dad Games Father's Day Fishing Derby and Brunch
Sat, Jun 6, 6:30 AM
Grasonville · 202 Wells Cove Rd
Going fast
6/3/26 - Connecting w/ Your Loved Ones - Medium Debbie @ Annapolis Crystals
Wed, Jun 3, 12:30 PM
Annapolis · Annapolis Crystals
Going fast
6/3/26 - Connecting w/ Your Loved Ones - Medium Debbie @ Annapolis Crystals
Wed, Jun 3, 12:30 PM
Annapolis · Annapolis Crystals
Going fast
Reflect & Create: A Multidimensional Health Workshop with Alicia & Casey
Thu, Jun 11, 6:30 PM
Annapolis · Annapolis Crystals
Going fast
Reflect & Create: A Multidimensional Health Workshop with Alicia & Casey
Thu, Jun 11, 6:30 PM
Annapolis · Annapolis Crystals
Confident & Capable: Women Raising Cattle
Fri, Jun 12, 9:00 AM
West River · 4956 Muddy Creek Rd
Confident & Capable: Women Raising Cattle
Fri, Jun 12, 9:00 AM
West River · 4956 Muddy Creek Rd
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
‘Just looking?’: Evaluating Risk in Online Behavior Course 2026
Mon, Jun 22, 8:00 AM
Annapolis · The Westin Annapolis
‘Just looking?’: Evaluating Risk in Online Behavior Course 2026
Mon, Jun 22, 8:00 AM
Annapolis · The Westin Annapolis
Paint for Paws with Beagle Rescue of Southern Maryland
Sun, Jun 7, 5:00 PM
Severna Park · Cypress Restaurant
Paint for Paws with Beagle Rescue of Southern Maryland
Sun, Jun 7, 5:00 PM
Severna Park · Cypress Restaurant
Trail Trotters 5k & Fun Run
Sun, Jun 7, 8:00 AM
Upper Marlboro · Promise Landing Farm, Inc
Trail Trotters 5k & Fun Run
Sun, Jun 7, 8:00 AM
Upper Marlboro · Promise Landing Farm, Inc
TCP Young Professionals Happy Hour & Blues FC Game
Wed, Jun 10, 5:00 PM
Annapolis · Navy-Marine Corps Memorial Stadium
TCP Young Professionals Happy Hour & Blues FC Game
Wed, Jun 10, 5:00 PM
Annapolis · Navy-Marine Corps Memorial Stadium

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