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Dating Events and Things to do in Annapolis, MD

Going fast
4th Annual Poodles & Ice Skate Jam
Tue, Jun 9, 7:00 PM
Odenton · Skate Zone Odenton
Going fast
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
Sunday at 4:45 PM
Annapolis · Annapolis City Dock
@@CANCELLED@@ The Hip Hop R&B Yacht Party Annapolis MD 6.7.2026
Sunday at 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
Sales end soon
Dad Games Father's Day Fishing Derby and Brunch
Saturday at 6:30 AM
Grasonville · 202 Wells Cove Rd
Sales end soon
Dad Games Father's Day Fishing Derby and Brunch
Saturday at 6:30 AM
Grasonville · 202 Wells Cove Rd
Vino & Vinyasa with Lindsay Cook at Great Frogs Winery
Wed, Jun 17, 6:00 PM
Annapolis · Great Frogs Winery
Vino & Vinyasa with Lindsay Cook at Great Frogs Winery
Wed, Jun 17, 6:00 PM
Annapolis · Great Frogs Winery
Almost full
6/3/26 - Connecting w/ Your Loved Ones - Medium Debbie @ Annapolis Crystals
Tomorrow at 12:30 PM
Annapolis · Annapolis Crystals
Almost full
6/3/26 - Connecting w/ Your Loved Ones - Medium Debbie @ Annapolis Crystals
Tomorrow at 12:30 PM
Annapolis · Annapolis Crystals
Almost full
Reflect & Create: A Multidimensional Health Workshop with Alicia & Casey
Thu, Jun 11, 6:30 PM
Annapolis · Annapolis Crystals
Almost full
Reflect & Create: A Multidimensional Health Workshop with Alicia & Casey
Thu, Jun 11, 6:30 PM
Annapolis · Annapolis Crystals
‘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
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
Sales end soon
Paint for Paws with Beagle Rescue of Southern Maryland
Sunday at 5:00 PM
Severna Park · Cypress Restaurant
Sales end soon
Paint for Paws with Beagle Rescue of Southern Maryland
Sunday at 5:00 PM
Severna Park · Cypress Restaurant
Sales end soon
Trail Trotters 5k & Fun Run
Sunday at 8:00 AM
Upper Marlboro · Promise Landing Farm, Inc
Sales end soon
Trail Trotters 5k & Fun Run
Sunday at 8:00 AM
Upper Marlboro · Promise Landing Farm, Inc
Sales end soon
JUNE GEMINI JAM featuring Kevin, Gina & Yahya
Thursday at 7:30 PM
Gambrills · Blue Dolphin Seafood Bar & Grill
Sales end soon
JUNE GEMINI JAM featuring Kevin, Gina & Yahya
Thursday at 7:30 PM
Gambrills · Blue Dolphin Seafood Bar & Grill
Almost full
Thomas Point Shoal Tour - Saturday, June 20th - 9:30 am
Sat, Jun 20, 9:30 AM
Annapolis · Dock Behind Annapolis Maritime Museum
Almost full
Thomas Point Shoal Tour - Saturday, June 20th - 9:30 am
Sat, Jun 20, 9:30 AM
Annapolis · Dock Behind Annapolis Maritime Museum
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
Mini Birth Class
Sat, Jun 13, 9:00 AM
Annapolis · AAMC - Clatanoff Pavilion
Mini Birth Class
Sat, Jun 13, 9:00 AM
Annapolis · AAMC - Clatanoff Pavilion
Laughs in the Lounge
Fri, Jun 12, 7:00 PM
Annapolis · Stan & Joe's Saloon
Laughs in the Lounge
Fri, Jun 12, 7:00 PM
Annapolis · Stan & Joe's Saloon
Going fast
Afro - Soca Wine Music & Food Festival Vendor Sign Up
Sun, Jun 21, 1:00 PM
Crownsville · Anne Arundel County Fairgrounds
Going fast
Afro - Soca Wine Music & Food Festival Vendor Sign Up
Sun, Jun 21, 1:00 PM
Crownsville · Anne Arundel County Fairgrounds
Pause & Reset: A Restorative Yoga & Meditation Experience for Women
Sat, Jun 13, 1:00 PM
Annapolis · Annapolis Athletic Club
Pause & Reset: A Restorative Yoga & Meditation Experience for Women
Sat, Jun 13, 1:00 PM
Annapolis · Annapolis Athletic Club
7th Annual Sundresses & Cigars
Sat, Jun 13, 4:00 PM
Mitchellville · Country Club At Woodmore
7th Annual Sundresses & Cigars
Sat, Jun 13, 4:00 PM
Mitchellville · Country Club At Woodmore
Almost full
3 week birth class series (AAMC) -IN PERSON
Tue, Jun 16, 4:30 PM
Annapolis · AAMC Belcher Pavilion
Almost full
3 week birth class series (AAMC) -IN PERSON
Tue, Jun 16, 4:30 PM
Annapolis · AAMC Belcher Pavilion

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