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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
Thursday at 6:30 PM
Annapolis · Maryland Hall
Almost full
Ballet Theatre of Maryland Annual Conservatory Showcase 2026
Thursday at 6:30 PM
Annapolis · Maryland Hall
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
Going fast
10th Annual Pints 4 Paws Homebrewing and Craft Beer Festival
Saturday at 2:00 PM
Annapolis · Naval-Marine Corps Stadium
Going fast
10th Annual Pints 4 Paws Homebrewing and Craft Beer Festival
Saturday at 2:00 PM
Annapolis · Naval-Marine Corps Stadium
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
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
Almost full
Crafted Tales™ Series
Friday at 7:00 PM
Upper Marlboro · The Free State Distillery, Inc
Almost full
Crafted Tales™ Series
Friday at 7:00 PM
Upper Marlboro · The Free State Distillery, Inc
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
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
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
Going fast
Chart House Prime - Duckhorn Wine Dinner
Thursday at 7:00 PM
Annapolis · Chart House Prime
Going fast
Chart House Prime - Duckhorn Wine Dinner
Thursday at 7:00 PM
Annapolis · Chart House Prime
Groove Spot Band & Show
Sun, Jun 21, 2:00 PM
Chesapeake Beach · The Bandshell at Rod 'N' Reel Resort
Groove Spot Band & Show
Sun, Jun 21, 2:00 PM
Chesapeake Beach · The Bandshell at Rod 'N' Reel Resort
@@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
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
April, The DIRTY GIRL, Entrepreneur MIXER
Sat, Jun 13, 7:00 PM
Upper Marlboro · 9101 Croom Acres Dr
Going fast
April, The DIRTY GIRL, Entrepreneur MIXER
Sat, Jun 13, 7:00 PM
Upper Marlboro · 9101 Croom Acres Dr
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
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
Johnny Seaton & Bad Behavior | Elvis Tribute
Sat, Jun 27, 7:00 PM
Chesapeake Beach · The Bandshell at Rod 'N' Reel Resort
Johnny Seaton & Bad Behavior | Elvis Tribute
Sat, Jun 27, 7:00 PM
Chesapeake Beach · The Bandshell at Rod 'N' Reel Resort
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
Going fast
Everyday Makeup Routine Makeup Tutorial Class (Calvert County, MD)
Sun, Jun 14, 1:30 PM
Dunkirk · Fresco Studios, LLC
Going fast
Everyday Makeup Routine Makeup Tutorial Class (Calvert County, MD)
Sun, Jun 14, 1:30 PM
Dunkirk · Fresco Studios, LLC
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

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:

American Voices United Through Song - June 6, 2026

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

The Alan Jackson Experience

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:

Ballet Theatre of Maryland Annual Conservatory Showcase 2026

Chart House Prime - Duckhorn Wine Dinner

Crafted Tales™ Series

10th Annual Pints 4 Paws Homebrewing and Craft Beer Festival