FALL FUN IN DORCHESTER COUNTY, MARYLAND

Updated October 24, 2024

Fall is in the air! Below are a few ways to embrace the season in Dorchester County on Maryland’s Eastern Shore with seasonal fun for all ages!

THE GREAT OUTDOORS THIS FALL

Fall is beautiful in the Heart of the Chesapeake. The air is cooler, the evening light lights up the marsh grasses with golden hues, the winds pick up for sailing. It's a great time of year for cycling, birding, fishing, boating, and the last few weeks of paddling before the winter chill sets in. We have free guides for cycling, birding, and paddling in Dorchester County. And you'll find more resources for outdoor adventure here. Plus, local seafood is especially delicious – Chesapeake blue crabs are at their plumpest and sweetest this time of year, and both wild harvested and farmed oysters are available for slurping.

FOR ALL AGES

Pick Your Own Pumpkins
Throughout October

Choose from lots of pumpkins and gourds while wandering through the pumpkin patch at Emily's Produce, or pick from the crates filled with different sizes and types. Don't miss this year's awesome pumpkin shelf (shown here)!

Corn Maze
Throughout the Fall

See if you can find your way through the twists and turns of the Emily’s Produce Corn Maze. Includes Fields of Fun entry and pumpkin patch and plenty of photo ops. Check for evening Sunset in the Stalks events with live music, extended market hours, and more. Plus, Flashlight Night in the Corn Maze is Nov. 9, 3-6pm.

Halloween Movies at Vintage Venue
Oct. 25, 26

Vintage Venue will show Halloween-themed movies on some weekend evenings at 6:30pm through October. They'll have props, snacks for purchase, and free crafts on some nights. Buy a membership with a one-time fee of $10 at Vintage Venue – ask for Crystal or Demi. Located at 415 Race St., Cambridge, MD. Check the latest schedule on their Facebook page.

Cambridge Ghost Walk
Oct. 25, 26; Nov. 1, 9, 16, 23, 30

Take a guided walk down Haunted High Street in Cambridge – the most haunted street in Maryland! Hear about the ghosts who haunt and strange events that have happened in just a few short blocks. Soldiers, Governors, jilted women, Oystermen, an eccentric cat lady, a dying daughter, slain war heroes, suicidal bankers, murderous merchants, laughing children and a one-legged sea captain are some of the spirits that hang around High Street. Reserve ahead.

Main Street Trick-or-Treat
Oct. 25, 4-7p
Bring the kids in costume for an evening of trick-or-treating in the Cambridge Main Street district. Participating locations include Ava's Pizzeria, Cambridge Main Street office (306 High St.), Butterfly Boutique, Choptank Tattoo, Dive Club, Main Street Gallery, RAR Brewing, Thomas' Fine Jewelry, Black Water Bakery, Blue Ruin, Cabin Feve Play Centre, Lil Bitta Bull BBQ, River Dogs, Shorelife Home & Gifts, Vintage 414, Vintage Venue.

Fall Harvest Fair
Oct. 25, 4:30pm
Pumpkin decorating contest, a costume contest, games, an educational area, crafts, and a trunk or treat. Admission is $2 per person with pre-registration or $5 the day of. Entering a pumpkin and the costume contest is free. Hosted by Dorchester County 4-H, Dorchester Recreation & Parks, and Dorchester County Farm Bureau.

Halloween with the Horses
Oct. 26, 1-3pm
Meet cows, alpacas, horses, donkey, miniature sheep, rabbits. All ages welcome. Trick or treating through the barn. Halloween cookie decorating and face painting. $10 per child; adults free. Costume contest 2pm. Buy tickets by Oct. 24.

Family Art Day: Pumpkins and Ghosts
Oct. 26, 11a-3p
Bring the family and choose either a ceramic ghost or pumpkin to paint and take home to celebrate Halloween! Led by Robert Gladney. All supplies provided. All children must be accompanied by a parent or guardian. You can drop in (arrive no later than 2:30pm), but pre-registration is suggested as supplies are limited. Register here.

Family Art Day: Celebrate Day of the Dead Skulls
Oct. 26, 1-3p
Learn how skulls are used for Day of the Dead celebrations in Mexican and Mexican American communities while you decorate one of your own ceramic pieces or painted canvas to take home! Led by Gray Jiménez. No experience necessary. All supplies provided. All children must be accompanied by a parent or guardian. You can drop in (arrive no later than 2:30pm), but pre-registration is suggested as supplies are limited. Register here.

Trunk or Treat - Photo courtesy Prodigal Creations

Trunk or Treat in Hurlock
Oct. 26, 11am-1pm

Hurlock Volunteer Fire Company hosts their annual Trunk or Treat. Wear your Halloween best! Contact hvfcauxiliary@gmail.com to enter or call/text 443-521-3232.

Trunk or Treat in the Neck District
Oct. 26, 5-7pm

Neck District Volunteer Fire Company hosts Trunk or Treat. Awards for best costume (kid and adult) and best decorated trunk. Food for sale to benefit NDVFD. Candy donations are appreciated. For more information, questions, and to RSVP for your parking spot, please call/text Ashley Howard 301-928-3651.

Trunk or Treat at YMCA
Oct. 26, 5-7pm

Robbins Family YMCA hosts music, costume parade, trunk decorating contest, crafts. Questions? Contact smajors@ymcachesapeake.org.

Trunk or Treat on Taylors Island
Oct. 27, 2-4pm

Slaughter Creek Marina and Palm Beach Willies host Trunk or Treat. Costumes encouraged with music and plenty of treats to be had. Hay Ride provided by the Andersons PBW will be hosting a family friendly party afterward with Karaoke by Chuckie LUV. Taylors Island Fire Company's new engine will be there for kids to see. Kids menu specials and games. Call Marina at 410-221-0050 or message us on Facebook to reserve a Trunk spot. Trunk or Treat 2-4pm; family-friendly after party 4-7pm.

Trunk or Treat at Cambridge Elks Lodge #1272
Oct. 27, 2-4pm

Elks Lodge #1272 and Cambridge Police Department for our annual Trunk or Treat. Bring the kids to a fun and safe afternoon of trick or treating. Anyone wanting to set up please message Kim at 410-200-8585.

Trunk or Treat at Pleasant Day Child Care Center
Oct. 27, 4-6pm

Join in the fun and check out their new childcare facility at 2474 Cambridge Beltway, Cambridge.

Trunk or Treat at IUCC
Oct. 27, 4:30-6pm

Children 12 and under will have the opportunity to "trick or treat" the decorated trunks of volunteer "treators.” For more information, and to reserve a spot for your "trunk", contact the church office at info@immanuelucc.faith or 410-228-4640 (M-Th, 9am-1pm).

Trick or Treat at the Cambridge Farmers Market
Oct. 31, 3-6pm
Come on out and support the Cambridge Farmers Market and get an early start on your trick or treating.

Fall Festival at Life's Energy Wellness Center
Oct. 31, 4-6pm
Games, food, fun. Come in costume. 317 High St., Cambridge.

Halloween at Old Trinity
Oct. 31, 4:30-6:30pm
Join in for Halloween at Old Trinity Church in Woolford. They'll have trick or treating in the historic cemetery and church grounds from 4:30-6pm.

Trunk or Treat with Prodigal Creations
Oct. 31, 6pm

Prodigal Creations of Cambridge hosts Trunk or Treat with extended store hours and more.

FOR THE ADULTS

Toast & Toasted at Layton's Chance Winery. Photo courtesy Layton's Chance

Halloween Karaoke
Oct. 25, 9pm-1am
Lil Bitta Bull BBQ hosts Halloween-themed karaoke and costume contest.

Halloween Dance and Costume Party
Oct. 26, 7-11pm
Sons of the American Legion Squadron 91 host annual Halloween Dance & Costume Party featuring Golden Touch. This event is open to the public. Costumes encouraged; there will be prizes! Tickets are available for $13 each and tables may be reserved for 6 or more. There will be a cash bar, food for purchase, 50/50 raffle, a baked goods raffle and of course, costume prizes! For tickets, please stop by the Post 91 Lounge or contact Don Wilcox at 443-521-7838.

Halloween Costume Party at Old Salty's
Oct. 26, 7-10pm
Cornhole tournament, costume contest with cash prizes, live music by Thunderball.

Toast & Toasted
Nov. 1, 6:30-9:30pm

Layton's Chance Winery hosts a fall evening with 4 unique s’more combinations paired with four different wines for 21 and over. Live music from Double Nickels. Roast marshmallows over the fire pits. Bring a chair & blanket if it's chilly! $20/person, 21+ only. Food trucks will NOT be provided; bring your own snacks and dinner. Tickets.

Halloween Party at Johnny's Tavern
Nov. 2, 9:30pm
Dress up and join Johnny's for their Halloween Party. DJ starting at 9:30. Drink specials. Prize for best costume.