8 Must-Visit Fall Festivals in Caroline County, Maryland

As the leaves turn golden and the crisp fall air sweeps across the Eastern Shore, Caroline County, Maryland, transforms into a hub of seasonal celebrations. From harvest festivals to cultural events, this hidden gem is the perfect place to embrace the beauty of autumn. Here are eight fall festivals in Caroline County that you won’t want to miss!

 

JZ Farms Fall Fest and Pumpkin Patch

Date: September through November 11, 2024
Location: Federalsburg, MD
Enjoy over 20 activities for children of all ages. Including a 10 acre corn maze celebrating 75 years of Peanuts, a kids corn maze, u-pick pumpkin and sunflower patch, 2 jumping pillows, Barnyard slingshot, Corn bin basketball, farm animals, Farmersville (featuring 13 playhouses), a ropes course, tire playground and so much more!
Don’t Miss: The corn maze is open during the evening, bring your flashlights and try for yourself

Bartenfelder Farms

Date: October 11-26, 2024
Location: Preston, MD
Come out to the farm for another great and haunted time. Enjoy the haunted hayride and haunted corn maze, a thrilling experience for all ages. The fun doesn’t stop there as you can expect a variety of food trucks, and sweet treats each night
Don’t miss: Fun day at the farm on October 18^th will feature pumpkin painting and carving, Halloween crafts, pony rides, and u-pick pumpkins and gourds.

Redemption Farms Fall Fest & Farm Tour

Date: October 12, 2024
Location: Denton, MD
Join us for a fun-filled day at Redemption Farms! Explore the beauty of autumn with pick-your-own pumpkins and apples, perfect for seasonal decorating or tasty treats. Enjoy a self-guided farm tour to see how everything grows and discover even more activities for the whole family. Mark your calendars and bring your family and friends for an unforgettable experience in the heart of fall season.

Ridgely Fall Festival

Date: October 12, 2024
Location: Ridgely, MD
Gear up for a day of affordable family fun, promoting fire prevention/safety month and supporting the Ridgely Volunteer Fire Department. Featuring bounce houses, kid’s games, music, first responder demonstrations, fire engine display, and plenty of food and rink available for purchase.
Don’t Miss: Our special Queens contest to see who will be crowned as RVFD ambassador

Hallowdaze

Date: October 19, 2024
Location: Preston, MD
This festival is worth the drive as the town of Preston again has Hallowdaze! This day comes filled with Halloween inspired events and activities. Shop our local vendors market, enjoy arts and crafts, corn hole, bounce houses and plenty of treats. Wear your best costume to enter the contest and earn prizes.
Don’t Miss: A live performance by the KG Band; a classic rock band with little funk and country too!

Spooktacular Fall Fest

Date: October 25, 2024
Location: Denton, MD
Join us for spine-tingling evening of family fun at our Spooktacular Fall Fest! This free event features music, and mesmerizing special effects. Indulge in delicious Halloween treats and wear your best costume for a tent-or-treat contest.
Don’t Miss: The all-new haunted house and tour!

Trick Trunk or Treat at the Mill

Date: October 27, 2024
Location: Preston, MD
Join in on the family friendly fun at the historic Linchester Mill. Trick Trunk or Treat, this annual event is sure to be exciting for all. Grab sweet treats from decorated trunks, enter as an individual or family to compete in the costume contest. Food trucks and local vendors will also be on hand and music all evening by DJ Mark Stivers.
Don’t Miss: A haunted trail along the Harriet Tubman trail at the mill and tarot readings.

Fall Fest Downtown Denton Main Street

Date: October 30, 2024
Location: Denton, MD
Denton’s historic downtown comes alive during this vibrant fall celebration. Enjoy shopping with local vendors, live music, and food trucks offering delicious fall flavors. The event is a great opportunity to explore the local shops and boutiques while enjoying the festive atmosphere.
Don’t Miss: The costume contest and pumpkin painting!

With an array of fall festivals that celebrate the rich agricultural history and vibrant community spirit, Caroline County offers something for everyone. Whether you’re into hands on farm experiences, live music, or exploring the great outdoors, there’s a fall event here that’s sure to make your autumn season unforgettable.

Pack your bags, bring your sense of adventure, and get ready to experience all that Caroline County has to offer this fall!

Feel free to personalize this itinerary with more local lodging options or dining experiences to make your visit even more memorable!