Annapolis Unique & Unusual Halloween Events 2026

19 unique & unusual Halloween events in Annapolis and nearby.

Annapolis gears up for Halloween with events hosted across theaters, historical sites, and unique venues. If you seek guided tales of the supernatural, consider the Haunted History Tour right here in Annapolis. For a different kind of artistic engagement a drive away, look to Baltimore's Make Your Own Glass Pumpkin workshop. Annapolis offers a spectrum of Halloween happenings. From ghost tours that delve into local lore to creative workshops and community gatherings, the season brings diverse activities to our region and nearby areas like Baltimore and Washington D.C.

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Illustration of costumed children and two witches on a lawn with pumpkins, a small tent and orange autumn trees

Family-Friendly Fall Activities

1 of 33 The Great Annapolis Pumpkins Annapolis

Colossal pumpkins weighing over 1,000 pounds

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 Illustration of a Halloween party at dusk with costumed characters around a punch bowl, a ghost, pumpkins and string lights

Food, Drink, and Parties

1 of 23 Halloween Baltimore 2026 at Maryland Science Center Baltimore

Multi-floor Halloween party with live music and immersive experiences

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 Illustration of a small haunted cottage with glowing windows, ghosts, jack-o'-lanterns and a black cat under a pale moon

Haunted Experiences

1 of 7 Bennett's Curse Haunted House Dundalk

Four indoor haunted attractions under one roof at Eastpoint Mall.

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 Illustration of a pumpkin character and a ghost performing on a small stage with red curtains before a costumed audience

Movies, Theater, and Entertainment

1 of 7 Halloween Movie Night & Costume Contest Easton

Free costume contest with movie screening

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Frequently Asked Questions

What does a full Halloween season in Annapolis cost, and how do we cap it?

The quiet total, farm day, haunt night, party, tour, costumes, candy, easily clears several hundred dollars per household. Cap it by picking one paid anchor per category you actually care about, filling the rest with free community events, and setting costume budgets before inspiration strikes. Early-bird tickets and weeknight pricing trim 20-30 percent off the same experiences.

What's the etiquette for cemetery tours around Annapolis?

You're a guest in an active memorial space: stay on paths, never touch or lean on monuments, keep voices low, and give any funeral or visiting family wide berth. Photography of headstones is usually fine on official tours, but follow the guide's guidance. Ghost-story framing doesn't suspend the respect rules, and daytime historical tours cover the same ground with better sightlines.

What do community Halloween events in Annapolis usually offer for kids?

The standard kit: costume parades with all-winners ribbons, craft stations, cookie decorating, face painting with a line worth budgeting 20 minutes for, candy stops, and a not-scary story corner. They're compact, usually two to three hours, so arrive at the start when supplies are full, since craft tables and candy famously run out early. Free almost always, donations welcome.

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