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Events and Things to do in Shady Side, MD

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Almost full
Ballet Theatre of Maryland Annual Conservatory Showcase 2026
Thu, May 28, 6:30 PM
Annapolis · Maryland Hall
Almost full
Ballet Theatre of Maryland Annual Conservatory Showcase 2026
Thu, May 28, 6:30 PM
Annapolis · Maryland Hall
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
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
Northeast Regional Fellowship- Thrive Conference
Thursday at 7:00 PM
Annapolis · Crowne Plaza Annapolis, an IHG Hotel
Sales end soon
Northeast Regional Fellowship- Thrive Conference
Thursday at 7:00 PM
Annapolis · Crowne Plaza Annapolis, an IHG Hotel
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
Sales end soon
Petty Coat Junction - Tom Petty Tribute
Thursday at 7:00 PM
Chesapeake Beach · The Bandshell at Rod 'N' Reel Resort
Sales end soon
Petty Coat Junction - Tom Petty Tribute
Thursday at 7:00 PM
Chesapeake Beach · The Bandshell at Rod 'N' Reel Resort
April, The DIRTY GIRL, Entrepreneur MIXER
Saturday at 7:00 PM
Upper Marlboro · 9101 Croom Acres Dr
April, The DIRTY GIRL, Entrepreneur MIXER
Saturday at 7:00 PM
Upper Marlboro · 9101 Croom Acres Dr
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
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
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
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
Almost full
Crafted Tales™ Series
Fri, May 29, 7:00 PM
Upper Marlboro · The Free State Distillery, Inc
Almost full
Crafted Tales™ Series
Fri, May 29, 7:00 PM
Upper Marlboro · The Free State Distillery, Inc
Going fast
In-person Lactation Basics - AAMC Annapolis, MD
Wednesday at 5:00 PM
Annapolis · 2000 Medical Pkwy
Going fast
In-person Lactation Basics - AAMC Annapolis, MD
Wednesday at 5:00 PM
Annapolis · 2000 Medical Pkwy
Going fast
The Heather Pierson Duo in Annapolis, MD
Tomorrow at 7:30 PM
Annapolis · 49 West Coffeehouse, Winebar & Gallery
Going fast
The Heather Pierson Duo in Annapolis, MD
Tomorrow at 7:30 PM
Annapolis · 49 West Coffeehouse, Winebar & Gallery
Sagittarius Full Moon Circle & Crystal Grid Workshop with Donna & Audrey
Sun, May 31, 10:30 AM
Annapolis · Annapolis Crystals
Sagittarius Full Moon Circle & Crystal Grid Workshop with Donna & Audrey
Sun, May 31, 10:30 AM
Annapolis · Annapolis Crystals
Going fast
Annapolis Kappas 11th Annual Bowling Bash
Sun, May 24, 8:00 PM
Annapolis · Annapolis Bowl
Going fast
Annapolis Kappas 11th Annual Bowling Bash
Sun, May 24, 8:00 PM
Annapolis · Annapolis Bowl
The Alan Jackson Experience
Fri, Jun 5, 7:00 PM
Chesapeake Beach · The Bandshell at Rod 'N' Reel Resort
The Alan Jackson Experience
Fri, Jun 5, 7:00 PM
Chesapeake Beach · The Bandshell at Rod 'N' Reel Resort

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:

Ballet Theatre of Maryland Annual Conservatory Showcase 2026

10th Annual Pints 4 Paws Homebrewing and Craft Beer Festival

American Voices United Through Song - June 6, 2026

The NoWhere Men

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:

The Heather Pierson Duo in Annapolis, MD

In-person Lactation Basics - AAMC Annapolis, MD

Northeast Regional Fellowship- Thrive Conference

Petty Coat Junction - Tom Petty Tribute