Fall Festivals Maryland

By popularity

SEP
5
FRI
Wine on the Beach Sept 5 & 6, 2025
FESTIVAL
Hugh T. Cropper Inlet Parking Lot
11:00 AM ·
$41
SEP
5
FRI
WATERSEDGE FALL FESTIVAL 2025
MUSIC
Watersedge Park
6:00 PM
SEP
7
SUN
Silver Spring Arts & Crafts End Of Sum…
FESTIVAL
Silver Spring Civic Center
2:00 PM
SEP
13
SAT
The Amish Outlaws @ Carroll County F…
MUSIC
Carroll County Agriculture Center & Are…
2:30 PM ·
$65
SEP
13
SAT
Old Line Country Festival
MUSIC
CAA Park
1:00 PM
SEP
14
SUN
Outlaw Music Festival: Willie Nelson, B…
MUSIC
Merriweather Post Pavilion
4:00 PM ·
$55
SEP
19
FRI
Mountain Highway @ Upperco Volunte…
MUSIC
Upperco Volunteer Fire Company
2:00 PM ·
$65
SEP
20
SAT
Annapolis Baygrass Festival 2025
MUSIC
Sandy Point State Park
3:00 PM
SEP
20
SAT
Annapolis Baygrass Festival 2025
MUSIC
Sandy Point State Park
7:00 PM
SEP
20
SAT
Upperco Music Festival 2025
MUSIC
Arcadia Carnival Grounds
7:00 PM
SEP
26
FRI
Oceans Calling Festival (Friday) with G…
MUSIC
Coconuts Beachfront Restaurant Bar
12:00 PM ·
$65
SEP
27
SAT
Ocean's Calling - Ocean City, MD
MUSIC
Coconuts Beachfront Restaurant Bar
12:00 PM
SEP
27
SAT
Fast Eddie & The Slowpokes @ The U…
MUSIC
The Union Mills Homestead
11:00 AM
SEP
28
SUN
Oceans Calling 2025
MUSIC
Coconuts Beachfront Restaurant Bar
12:00 PM
SEP
28
SUN
Milburn Stone Folk Festival
MUSIC
Milburn Stone Theatre
2:00 PM
OCT
3
FRI
Ocean City MD - 2025 Country Calling …
MUSIC
Coconuts Beachfront Restaurant Bar
12:00 PM ·
$65
OCT
3
FRI
Country Calling Festival - 3 Day Pass w…
MUSIC
Coconuts Beachfront Restaurant Bar
3:30 AM ·
$407
OCT
5
SUN
Ocean City MD - 2025 Country Calling …
MUSIC
Coconuts Beachfront Restaurant Bar
12:00 PM ·
$65