The Great Annapolis Pumpkins
Colossal pumpkins weighing over 1,000 pounds
Annapolis Family-Friendly Fall Activities 2026
33 family-friendly fall activities in Annapolis and nearby.
Annapolis families can find Halloween entertainment at various locations.
Consider the Maryland Corn Maze in Gambrills for outdoor activities, or the Halloween Trunk or Treat at the Glen Burnie Library for a convenient community event.
All Family-Friendly Fall Activities Around Annapolis
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Food, Drink, and Parties
1 of 24
Halloween Baltimore 2026 at Maryland Science Center
Baltimore
Multi-floor Halloween party with live music and immersive experiences
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Haunted Experiences
1 of 8
Bennett's Curse Haunted House
Dundalk
Four indoor haunted attractions under one roof at Eastpoint Mall.
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Movies, Theater, and Entertainment
1 of 7
Halloween Movie Night & Costume Contest
Easton
Free costume contest with movie screening
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Unique & Unusual
1 of 20
Annapolis Ghost Tours & Crawls
Annapolis
Exterior-only leisurely ghost walk visiting Annapolis' horrific haunted sites
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Find Family-Friendly Halloween Fun on Our Map!
See all trunk-or-treats, pumpkin patches, and kid-friendly events nearby.
Frequently Asked Questions
What hygiene plan makes petting zoos at Annapolis farms less risky?
The rule: animals, then handwash, then food, in that exact order, every time. Use the farm's wash stations rather than sanitizer alone when hands touch animals or fences, keep pacifiers and sippy cups in the bag near animals, and don't let kids eat inside the enclosure. Strollers stay outside pens. It's two minutes of routine that prevents the classic post-farm stomach bug.
How accessible are pumpkin patches and fall festivals near Annapolis for wheelchairs?
Farm terrain is the challenge: grass, gravel, and rutted fields vary by venue and by how much rain fell that week. Call and ask about packed paths, accessible restrooms and parking, and whether the picking field has a firm route, since some farms bring pumpkins to a paved area on request. Festivals on fairgrounds or paved lots are the safer default.
Can we bring our dog to pumpkin patches or fall festivals in Annapolis?
Policies split hard: many farms ban pets outright for animal-safety and food rules, while some festivals welcome leashed dogs and even run costume contests for them. Check the venue's FAQ the day before, never assume. If dogs are allowed, bring water, keep them clear of petting zoos and food lines, and be honest about whether crowds plus kids stress your dog.