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Events and Things to do in Shady Side, MD

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Almost full
Groove Spot Band & Show Concert at Rod 'N' Reel Resort
Saturday at 7:30 PM
Chesapeake Beach · Chesapeake Ballroom at Rod 'N' Reel Resort
Almost full
Groove Spot Band & Show Concert at Rod 'N' Reel Resort
Saturday at 7:30 PM
Chesapeake Beach · Chesapeake Ballroom at Rod 'N' Reel Resort
10th Annual Pints 4 Paws Homebrewing and Craft Beer Festival
Sat, May 30, 2:00 PM
Annapolis · Naval-Marine Corps Stadium
10th Annual Pints 4 Paws Homebrewing and Craft Beer Festival
Sat, May 30, 2:00 PM
Annapolis · Naval-Marine Corps Stadium
Sales end soon
Taste of Spring on West Street 2026
Sunday at 1:00 PM
Annapolis · 53 West St
Sales end soon
Taste of Spring on West Street 2026
Sunday at 1:00 PM
Annapolis · 53 West St
Northeast Regional Fellowship- Thrive Conference
Thu, May 21, 7:00 PM
Annapolis · Crowne Plaza Annapolis, an IHG Hotel
Northeast Regional Fellowship- Thrive Conference
Thu, May 21, 7:00 PM
Annapolis · Crowne Plaza Annapolis, an IHG Hotel
Petty Coat Junction - Tom Petty Tribute
Thu, May 21, 7:00 PM
Chesapeake Beach · The Bandshell at Rod 'N' Reel Resort
Petty Coat Junction - Tom Petty Tribute
Thu, May 21, 7:00 PM
Chesapeake Beach · The Bandshell at Rod 'N' Reel Resort
April, The DIRTY GIRL, Entrepreneur MIXER
Sat, May 23, 7:00 PM
Upper Marlboro · 9101 Croom Acres Dr
April, The DIRTY GIRL, Entrepreneur MIXER
Sat, May 23, 7:00 PM
Upper Marlboro · 9101 Croom Acres Dr
Going fast
DC Black Pride Ultimate Pool Party
Sun, May 24, 6:00 PM
Upper Marlboro · DC Black Pride Ultimate Pool Party
Going fast
DC Black Pride Ultimate Pool Party
Sun, May 24, 6:00 PM
Upper Marlboro · DC Black Pride Ultimate Pool Party
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
Vino & Vinyasa with Lindsay Cook at Great Frogs Winery
Sun, May 31, 11:00 AM
Annapolis · Great Frogs Winery
Vino & Vinyasa with Lindsay Cook at Great Frogs Winery
Sun, May 31, 11:00 AM
Annapolis · Great Frogs Winery
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
Sales end soon
Third Friday Comedy at the Crabb Shack
Tomorrow at 8:00 PM
Edgewater · The Crab Shack Edgewater
Sales end soon
Third Friday Comedy at the Crabb Shack
Tomorrow at 8:00 PM
Edgewater · The Crab Shack Edgewater
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
The Hip Hop R&B Yacht Party Annapolis MD 6.7.2026
Sun, Jun 7, 4:45 PM
Annapolis · Annapolis City Dock
The Hip Hop R&B Yacht Party Annapolis MD 6.7.2026
Sun, Jun 7, 4:45 PM
Annapolis · Annapolis City Dock
The NoWhere Men
Sat, May 30, 7:00 PM
Chesapeake Beach · The Bandshell at Rod 'N' Reel Resort
The NoWhere Men
Sat, May 30, 7:00 PM
Chesapeake Beach · The Bandshell at Rod 'N' Reel Resort
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
Going fast
In-person Lactation Basics - AAMC Annapolis, MD
Wed, May 20, 5:00 PM
Annapolis · 2000 Medical Pkwy
Going fast
In-person Lactation Basics - AAMC Annapolis, MD
Wed, May 20, 5:00 PM
Annapolis · 2000 Medical Pkwy
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
Sales end soon
The Heather Pierson Duo in Annapolis, MD
Monday at 7:30 PM
Annapolis · 49 West Coffeehouse, Winebar & Gallery
Sales end soon
The Heather Pierson Duo in Annapolis, MD
Monday at 7:30 PM
Annapolis · 49 West Coffeehouse, Winebar & Gallery
Sales end soon
151st Preakness Watch Party
Saturday at 4:00 PM
Upper Marlboro · The Free State Distillery, Inc
Sales end soon
151st Preakness Watch Party
Saturday at 4:00 PM
Upper Marlboro · The Free State Distillery, Inc
Going fast
Crafted Tales™ Series
Fri, May 29, 7:00 PM
Upper Marlboro · The Free State Distillery, Inc
Going fast
Crafted Tales™ Series
Fri, May 29, 7:00 PM
Upper Marlboro · The Free State Distillery, Inc

Trends in Shady Side

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Frequently asked questions about Shady Side

What are the best events to attend?

According to Eventbrite, the best events are:

10th Annual Pints 4 Paws Homebrewing and Craft Beer Festival

Northeast Regional Fellowship- Thrive Conference

Petty Coat Junction - Tom Petty Tribute

April, The DIRTY GIRL, Entrepreneur MIXER

Which events are currently trending in Shady Side?

The trending searches this month in Shady Side are:

wig install classes

Which events are coming up?

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

Third Friday Comedy at the Crabb Shack

151st Preakness Watch Party

Groove Spot Band & Show Concert at Rod 'N' Reel Resort

Taste of Spring on West Street 2026