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Events and Things to do in Annapolis, MD

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Going fast
DMV R&B Wine Festival
Sat, Jun 20, 1:00 PM
Crownsville · Anne Arundel County Fairgrounds
Going fast
DMV R&B Wine Festival
Sat, Jun 20, 1:00 PM
Crownsville · Anne Arundel County Fairgrounds
Sales end soon
American Voices United Through Song - June 6, 2026
Saturday at 7:30 PM
Annapolis · Maryland Hall
Sales end soon
American Voices United Through Song - June 6, 2026
Saturday at 7:30 PM
Annapolis · Maryland Hall
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
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
Rock the Dock
Today at 6:00 PM
Annapolis · Annapolis Maritime Museum & Park
Rock the Dock
Today at 6:00 PM
Annapolis · Annapolis Maritime Museum & Park
Going fast
21ST ANNUAL DMV & BEYOND CAR, MOTORCYCLE, & TRUCK CRUISE-IN!
Saturday at 2:00 PM
Lothian · Geno's Ball Park
Going fast
21ST ANNUAL DMV & BEYOND CAR, MOTORCYCLE, & TRUCK CRUISE-IN!
Saturday at 2:00 PM
Lothian · Geno's Ball 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
Almost full
4th Annual Poodles & Ice Skate Jam
Tuesday at 7:00 PM
Odenton · Skate Zone Odenton
Almost full
4th Annual Poodles & Ice Skate Jam
Tuesday at 7:00 PM
Odenton · Skate Zone Odenton
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
@@CANCELLED@@ The Hip Hop R&B Yacht Party Annapolis MD 6.7.2026
Sunday at 4:45 PM
Annapolis · Annapolis City Dock
Sales end soon
@@CANCELLED@@ The Hip Hop R&B Yacht Party Annapolis MD 6.7.2026
Sunday at 4:45 PM
Annapolis · Annapolis City Dock
Going fast
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
Going fast
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
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
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
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
Sales end soon
Confident & Capable: Women Raising Cattle
Fri, Jun 12, 9:00 AM
West River · 4956 Muddy Creek Rd
Sales end soon
Confident & Capable: Women Raising Cattle
Fri, Jun 12, 9:00 AM
West River · 4956 Muddy Creek Rd
Going fast
Paint for Paws with Beagle Rescue of Southern Maryland
Sunday at 5:00 PM
Severna Park · Cypress Restaurant
Going fast
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
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
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

Trends in Annapolis

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Frequently asked questions about Annapolis

What are the best events to attend?

According to Eventbrite, the best events are:

DMV R&B Wine Festival

Afro - Soca Wine Music & Food Festival

Josh Wallace 2nd Annual Youth Football Camp

PT. 2 ON THE WATER

Which events are currently trending in Annapolis?

The trending searches this month in Annapolis are:

anne arundel county

kentucky derby maryland

Which events are coming up?

Discover the best events happening soon – you don't want to miss them:

Dad Games Father's Day Fishing Derby and Brunch

21ST ANNUAL DMV & BEYOND CAR, MOTORCYCLE, & TRUCK CRUISE-IN!

American Voices United Through Song - June 6, 2026