ENJOY THE HOLIDAY SEASON IN RIDGELY MARYLAND
Christmas in Ridgely
Winterfest of Lights
November 25, 2026–January 2, 2027
FREE! Visit our award-winning light display – the largest in the county and one of the largest on the Shore. Capture memorable moments at the selfie stations as you stroll along the paved Rails-to-Trails pathway. Illuminated nightly starting at 5 pm.
Caroline County Humane Society’s
PAWS & CLAUS
Friday November 27, 2026, 5–8 pm
Help support the Caroline County Humane Society. Bring your furry family members to the Ridgely Train Station for visits and photos with Santa!
1 W. Railroad Ave, Ridgely
Ridgely Lions Club Christmas Parade •
Ridgely Lions Club Christmas Parade •
Ridgely Lions Club
Christmas Parade
Saturday, December 5, 2026
6:45 pm
Line-up at 6:15 PM at Martin Sutton Park 4th Street Parking Lot.
Santa will be at the train station after the parade for visits!
For more information contact the Ridgely Lions Club:
rlcstrawberryfestival@gmail.com
SANTA ROCKS RIDGELY!
SANTA ROCKS RIDGELY!
Santa Rocks Ridgely
December 1–22, 2026
Find a Santa Rock and
bring it to the Town Hall
for a prize!
WINTER FESTIVAL
WINTER FESTIVAL
The Award-Winning
Christmas in Ridgely
Winter Festival
Bring the entire family for an evening of Christmas magic.
FIREWORKS!!!
Ice Skating, Train Rides, & Inflatable Amusements ALL FREE!!!
Vendors, Food Trucks, Beer & Wine
Fun for the whole family!
Saturday, December 12, 2026,
4–8 pm
Fireworks begin at 8 pm
Railroad Memorial Park,
Ridgely, MD
Raindate:
Saturday, December 19, 2026
Holiday Paint Night
Holiday Paint Night
Fundraiser for Winter Festival
Friday, December 4, 2026, 6:30 pm
Join us at Cowbarn Events
101 Cowbarn Rd., Ridgely,
for holiday paint night.
Cost is $50 and includes all art supplies, instruction, drinks &
light refreshments.
Register online or at the
Ridgely Town Hall, 2 Central Avenue.
TO SIGN UP CLICK THE LINK BELOW:
https://christmasridgely.betterworld.org/events/christmas-ridgely-paint-night-20-21
A Very Grinchy Breakfast &
Holiday Painting
Saturday, December 5, 2026
8:30–10:30 am
Eat, paint, and be grumpy! Join the Grinch for a holiday breakfast and paint party at Cowbarn Events. The Grinch will be there to welcome and visit with each guest.
$35 cost includes art supplies, instruction, and continental style breakfast. Breakfast is at 8:30 and painting begins promptly at 9:00. Children under 4 must have parental assistance.
Register online or at the
Ridgely Town Hall, 2 Central Avenue.
TO SIGN UP CLICK THE LINK BELOW:
https://christmasridgely.betterworld.org/events/christmas-ridgely-paint-night-20-21
Bells of St. Benedict
Christmas Bazaar
Saturday, December 12, 2026,
9 am–4 pm
St. Benedict Parish Hall
Breakfast & Lunch food, Vendors, Ticket Auction, Petting Zoo, Kids Activities, Parish Market, Cookie Boxes, Music & Performances, Visits with Santa & Mrs. Claus. Christmas magic awaits!
Ridgely Historical Society
Annual Christmas
Decorating Contest
December 20, 2026, 6 pm
Ridgely residents and businesses are encouraged to decorate for the holiday. Guest judges will pick the winners and prizes will be awarded. Good Luck!
Ridgely Volunteer Fire Department Escorts Santa though Ridgely
December TBD, 2026,
Beginning at 5 pm outside of town limits
December TBD, 2026,
Beginning at 5 pm inside of town limits
