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Got your costume ready? Here are thirty or so reasons to get to work on that, listed (roughly speaking) chronological order:

• It’s that time of year again. Chesapeake Ghost Tours will be leading spooky walks in 11 different towns, exploring the history and “mysteries” of the region with a focus on the spookier of those “mysteries.” Details.

• The Pocomoke (Md.) Fall Festival on Sat., Oct. 8 is a Halloween-themed downtown block party with costume contest, pumpkin painting, petting zoo, hay rides, and more. Details.

• See “Little Shop of Horrors” at the Clear Space Theatre in Rehoboth Beach, Del., Oct. 14-30. Details.

• Set aside Sat., Oct. 15 if you’d like to be part of a zombie invasion of Milton, Del. The Zombie Fest there includes makeup stations, costume contests, kids’ activities, live music, carnival freak shows, acrobatic aerialists, and more. At 8pm the zombie nation will commence marching through town, so you might want to practice that half-dead waddle. Details.

• Hop on over to the Hippie Halloween party at Tammy’s Cool Things on the highway in Trappe, Md. on Sat. Oct 15. There will be We will have music, vendors, arts, crafts, free pony rides, a bounce house, and more.
Details.

• Learn about the Legends of Delmarva, including some spooky ones, in presentations at the Delmarva Discovery Museum in Pocomoke City, Md. on the weekend of Oct. 15 and 16. Details.

• In Camden, Del. on Sat., Oct. 15 children 2 to 7 years old are invited to go trick or treating along a Fantasy Trail route that will have them meeting some of their favorite cartoon and storybook characters. Details.

Great Pumpkin Race in Ocean City on the Eastern Shore of Maryland• Most of the fun Halloween traditions in Ocean City, Md.–including the Great Pumpkin Race, the Halloween Beach Maze, and the hayrides–have been folded into the big Sunfest party on the long weekend of Oct. 20-23. Details.

• Celebrate Halloween in the Forest at the Furnace Town Historic Site near Snow Hill, Md. on the evening of Saturday, Oct. 22. Trick or treating, games, crafts, and more. Scroll down to date here for details.

• The Milton (Del.) Theatre will have a live production of the “Rocky Horror Picture Show,” Oct. 13-22, and a local-student production of “Night of the Living Dead: The Musical,” Oct. 27-29. Details.

• In a sweet local tradition dating back to the 1930s, the Milford (Del.) Halloween Parade is happening on Wed., Oct. 19. Details.

• The Milford (Del.) Museum is putting on a guided Ghost Walk full of creepy and macabre tales on Sat., Oct. 22. Details.

• Centreville (Md.) Day on Sat., Oct. 22 is a fall festival held around the town’s gorgeous old courthouse. Talent shows, pumpkin bowling, PacMan tournament, pumpkin painting, and the prestigious “Great Centreville Cookie Contest.” Details.

Witches of Rock Hall 2021 Halloween on Eastern Shore of Maryland• Tour a “Halloween Ghost Ship” inside the Copeland Maritime Center in Wilmington, Del. on Sat., Oct 22. Plus, crafts, pumpkin painting, and a costume parade. The magnificent Kalmar Nyckel replica sailing ship will be docked outside, open for tours. Details.

• The annual Fall into St. Michaels (Md.) weekend on Oct 22 and 23 has pumpkin carving, scarecrow, and pie-cooking contests, along with the popular Jack Russell Terrier races. No worries, there is a category called “So Your Dog Thinks He’s a Jack.” Details.

• Learn about the Haunted Pocomoke Forest in a presentation at the Delmarva Discovery Museum in Pocomoke City, Md. on the weekend of Oct 22 and 23. Details.

• The Millsboro (Del.) Autumn Fest on Sun., Oct. 23 will have vendors, music, pie contest, pumpkin carving, and more. Details.

• The Fall Festival in Seaford, Del. on Sun., Oct. 23 will be held on the pretty grounds of the Governor Ross Mansion and Plantation there. Think trunk-n-treat, hay rides, games, and more. Details.

• Reserve in advance if you want the little one(s) in your life to wander the Whimsical Woods in Bethany Beach, Del. on Tue./Wed., Oct. 25/26. Trick-or-treat through a forest filled with fantasy characters. Wander a Haunted Greenhouse. Light fare, refreshments, more. Details.

• The ice rink at the Talbot County Community Center near Easton, Md. is throwing a BOOnanza ice-skating costume bash on Wed., Oct. 26. Details.

• Get the scoop on the ancient roots of Halloween traditions when Dr. Elizabeth Ragan of Salisbury University talks about “Samhain, All Hallows, and Los Muertos: The Many Guises of Halloween” on Thurs., Oct. 27 at the Ward Museum in Salisbury, Md. Details.

• Author Josh Hitchens will be spinning stories about spooky, haunted places in Delaware in a talk at the library in Bethany Beach, Del. on Thurs., Oct. 27. Details.

• The popular Children’s Fantasy Trail at Cape Henlopen Park near Lewes, Del. on Friday, Oct. 28 will have children trick or treating with their favorite storybook characters. Details.

• During Boos & Brews at the Lewes (Del.) Historical Society on Fri., Oct. 28, you will wander the grounds meeting spirits from days gone by while enjoying food, brews (including Witch’s Brew), and music. Details.

Milton Zombie Fest Halloween on Delmarva• The sinister side of Delaware’s capital city will be front and center during the Dark Dover Lantern Tours on Oct. 28 and 29. Details.

• The Poplar Hill Mansion near downtown Salisbury, Md. has a Halloween Party on Fri., Oct. 28 with dancing and storytelling (by Andy Nunez) and then a kids-oriented Jack O’ Lantern Jubilee on Sat., Oct. 29. Click events here for details.

• Downtown Snow Hill will have a Halloween parade followed by a downtown block party on Green Street on Sat., Oct. 29. Dress to impress! Details.

• The humongous Sea Witch Festival returns to Rehoboth Beach, Del., on Halloween weekend, Oct 28 to 30. More than 100 different events, highlighted by a Saturday morning parade down the main drag filled with giant balloons, marching bands, colorful mummer bands, and costumed creatures. If past years are any guide, think Haunted Bonfire Beach Party, Creepy Graveyard Trail, and much, much more. Details.

• Put on your best costume to match the theme during Witches Weekend and head to Rock Hall, Md., Oct. 28-30. There will be dress-up fun with paddling, the blinging of brooms, a bewitching meditation session, bocce ball, cornhole, and more. Be sure to find your way to the group beach photo session. Details.

• Schellville in Rehoboth Beach will be putting on its first-ever Wicked Brew Bash on Sat., Oct. 29. A dozenish local breweries, food trucks, live music. Details.

Happy Halloween Skipjack from Eastern Shore of Maryland• Local police are putting on a Cops and Goblins Festival in John West Park in Ocean View, Del. on Sat., Oct. 29. Costume contest, petting zoo, snacks, etc. Details.

• On Sat., Oct. 29, Bethany Beach, Del. is throwing a Wags, Witches & Warlocks party with a parade, costume contest, trick or treating, crafts, etc. Details.

• The festivities during Wicked Weekend in Milton, Del. on Sat., Oct. 29 will include trick-or-treating, pumpkin painting, a haunted train ride, and more. Details.

• The Halloween festivities in Cape Charles, Va. take on a theatrical touch with a production of “A Night of Gothic Horror” at the Palace Theatre, Oct. 28 to 30. Details.

–posted by Jim Duffy for Secrets of the Eastern Shore/Whimbrel Creations LLC on Sept. 21, 2022. Thanks for spending a little time on this page and wandering around this site!

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