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Festivals in Shady Side, MD

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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
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
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
Marlboro Day
Sat, Jun 6, 10:00 AM
Upper Marlboro · Governor Oden Bowie Drive
Marlboro Day
Sat, Jun 6, 10:00 AM
Upper Marlboro · Governor Oden Bowie Drive
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
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
2026 East Coast Thunder
Sun, May 24, 11:00 AM
Stevensville · American Legion Post 278
2026 East Coast Thunder
Sun, May 24, 11:00 AM
Stevensville · American Legion Post 278
Going fast
Meet & Greet Breakfast with the Artists
Thu, Jul 16, 10:00 AM
Upper Marlboro · Wellspring Manor & Spa
Going fast
Meet & Greet Breakfast with the Artists
Thu, Jul 16, 10:00 AM
Upper Marlboro · Wellspring Manor & Spa
Sales end soon
The Laicos Club Presents Barrel & Smoke
Thursday at 6:00 PM
Mitchellville · Country Club At Woodmore
Sales end soon
The Laicos Club Presents Barrel & Smoke
Thursday at 6:00 PM
Mitchellville · Country Club At Woodmore
H.E.R Village Wellness Experience
Sat, Jun 27, 11:00 AM
Annapolis · 932 Windsor Ave
H.E.R Village Wellness Experience
Sat, Jun 27, 11:00 AM
Annapolis · 932 Windsor Ave
The Author Space Book & Art Festival
Sat, Nov 14, 10:00 AM
Upper Marlboro · The Show Place Arena
The Author Space Book & Art Festival
Sat, Nov 14, 10:00 AM
Upper Marlboro · The Show Place Arena
Hamlets Aloha Jazz Fest
Sat, Jun 20, 4:00 PM
Odenton · Hamlet Clubhouse Pavilion
Hamlets Aloha Jazz Fest
Sat, Jun 20, 4:00 PM
Odenton · Hamlet Clubhouse Pavilion
Lammastide: The First Harvest
Sat, Aug 8, 3:00 PM
Glenn Dale · Glenn Dale Volunteer Fire Department
Lammastide: The First Harvest
Sat, Aug 8, 3:00 PM
Glenn Dale · Glenn Dale Volunteer Fire Department
Almost full
2026 Fall Craft Fair
Sat, Nov 14, 10:00 AM
Pasadena · Chesapeake High School
Almost full
2026 Fall Craft Fair
Sat, Nov 14, 10:00 AM
Pasadena · Chesapeake High School
Psychic Affairs of Maryland - November 2026
Sun, Nov 8, 9:00 AM
Gambrills · Bowie Elks Lodge No 2309
Psychic Affairs of Maryland - November 2026
Sun, Nov 8, 9:00 AM
Gambrills · Bowie Elks Lodge No 2309
Taste of Seton
Sat, May 30, 6:00 PM
Bladensburg · Elizabeth Seton High School
Taste of Seton
Sat, May 30, 6:00 PM
Bladensburg · Elizabeth Seton High School
CAACO Juneteenth Celebration
Sat, Jun 20, 12:00 PM
Cheverly · 6401 Forest Rd
CAACO Juneteenth Celebration
Sat, Jun 20, 12:00 PM
Cheverly · 6401 Forest Rd
Just added
3rd Anne Arundel Asian American Pacific Islander Festival
Sun, May 31, 11:30 AM
Crownsville · Anne Arundel County Fairgrounds
Just added
3rd Anne Arundel Asian American Pacific Islander Festival
Sun, May 31, 11:30 AM
Crownsville · Anne Arundel County Fairgrounds
Summer Psychic Fair
Sun, Jul 19, 9:30 AM
Severn · Glen Burnie Elks Lodge #2266
Summer Psychic Fair
Sun, Jul 19, 9:30 AM
Severn · Glen Burnie Elks Lodge #2266
Going fast
The Official Summer Opener - #CapHouseFest Salutes Sam The Man Burns 2026
Saturday at 11:00 AM
Washington · Alethia Tanner Park
Going fast
The Official Summer Opener - #CapHouseFest Salutes Sam The Man Burns 2026
Saturday at 11:00 AM
Washington · Alethia Tanner Park

Trends in Shady Side

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Frequently asked questions about Shady Side

What are the best festival events to attend?

According to Eventbrite, the best festival events are:

DMV R&B Wine Festival

Afro - Soca Wine Music & Food Festival

DMV R&B Wine Festival Vendor Sign Up

Which events are currently trending in Shady Side?

The trending searches this month in Shady Side are:

wig install classes

Which festival events are coming up?

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

The Laicos Club Presents Barrel & Smoke

The Official Summer Opener - #CapHouseFest Salutes Sam The Man Burns 2026

2026 East Coast Thunder

10th Annual Pints 4 Paws Homebrewing and Craft Beer Festival