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Autumn has arrived in Caroline County! From pumpkin patches and orchards to hayrides and haunted happenings, here are a few ways to celebrate fall in Caroline County, MD! This list is updated regularly, so check back for more October fun! View our full online calendar here.

Fall Fest at JZ Farms
JZ Farms Fall Fest is a season-long celebration featuring more than 20 activities for children of all ages! Activities include a 10-acre corn maze, a kiddie maze, Farmersville, two jumping pillows, corn bins, farm animals, tire playground, a U-Pick pumpkin patch, paintball and more! The farm is located at 6526 Dion Road in Federalsburg, and they are open Thursdays through Sundays from 10am – 5pm through October 30th!

Haunted Hayride at Bartenfelder Farms
Feeling brave? Head to Bartenfelder Farms, located at 4110 Payne Road in Preston for a spook-tacular Haunted Hayride on October 14th, 15th, 21st and 22nd! They also have food, a corn maze, and a bounce house open all day. The hayride is $8/person.

Apple Picking at Redemption Farms
Looking to pick your own apples? Redemption Farms, located at 26564 Hignutt Road in Denton, has a u-pick orchard and a farm market that is open Monday through Saturday from 10am-6pm!

Cider Fest at Harvest Ridge Winery on October 15th
Harvest Ridge Winery invites you to Head to Rebel Seed Cider Fest, a fun-filled day featuring cider, food, music and games! Find out more here.

Federalsburg Heritage Day & Bicentennial Sneak Peak Party on October 15
Federalsburg is the place to be on October 15th! Celebrate the town at Heritage Day, a free, fun-filled day celebrating Federalsburg’s vibrant history! Stop by the museum to view the many displays and demonstrations on a wide variety of subjects such as broom making, spinning wheels, painting and competition chickens. Colonel Richardson HS graduate Mitch Northam will be showcasing his book, “High School Basketball on Maryland’s Eastern Shore: A Shore Hoops History.” For the automobile buff, there will be an outdoor display of antique vehicles to enjoy as well.  There will be food and beverages available for purchase.

Later that day is the Federalsburg Bicentennial Speak Peek Party! The evening will include food, drinks, entertainment, and information about their upcoming Bicentennial Celebration schedule for 2023. Tickets can be purchased online at or in person at the Federalsburg Town Hall. Find out more here.

Howl-o-Ween 5K on October 22nd
Come out to the Howl-O-Ween 5k Run/Walk to benefit the Caroline County Humane Society on October 22nd! The race starts at Martin Sutton Memorial Park, located on Rt. 480 (or West 6th Street) and Park Avenue in Ridgely, MD. This flat-loop course includes the town’s rail trail and scenic farmland. Registration is $25/participant until October 21st and $30 day of event for adults or $15/participant until October 21 and $20 day of event for racers ages 13 and under. All participants will receive a race t-shirt. Registration opens at 8am, and race begins at 9am. Find out more and register online at

Beer Garden at Adkins Arboretum on October 22nd
Adkins Arboretum invites you to enjoy libations and live music by Dell Foxx Company at their inaugural Beer Garden on October 22nd! Since their first performance in 2014, local favorites Dell Foxx Company have developed a repertoire that ranges from Alabama Shakes to Grand Funk Railroad to Florence and the Machine. Groove to the band as you grab a hula hoop, play corn hole, or take a walk. Beer from Bull and Goat Brewery and Ten Eyck Brewing Company and food from Blue Monkey Street Tacos and So Coast Street Eats will be available for purchase. Find out more and get your tickets here. 

Halloween Dodgeball Tournament on October 22nd
You won’t want to miss this spooktacular Halloween Dodgeball Tournament on Saturday, October 22nd at North Caroline High School at 3pm! This event will feature prizes, costumes, and fun for all! Co-ed divisions include Middle School, High School, and Open Division. $40 per team, with a three game guarantee. Find out more here.