Looking for Annapolis fall and Halloween events in 2026? You're in the right place!
We rounded up every pumpkin patch, trunk-or-treat, and spooky-but-family-friendly event happening in Annapolis this season — so you can stop scrolling ten different Facebook groups and just scroll this list instead. New events added daily during the busy season, so bookmark this page!
New events are added daily during this busy season, so bookmark this page and check back often!
Last updated: September 17th — we update this constantly, so bookmark it!
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🍁 Can't-Miss Fall Attractions Near Annapolis
Bookmark these! They're the spots families come back to year after year. They're not in Annapolis, but too far away and worth the drive! Find here who is on our must-visit list this season:
Farm Fun For All Ages
- Maryland Corn Maze, Gambrills — Farm with 8 acre corn maze and offers apple cider, pumpkins, petting farm, kettle corn, pony rides, hay rides, apple cider donuts, web swings, apple cider slushes, hay pyarmid, and a retail store.
- Montpelier Farms, Upper Marlboro — Lots of fall farm festivities including animals, playgrounds, a trike track, barnyard basketball, giant hill slides, ride-on pig races, food and drink, and farm markets.
- The Backyard, Pasadena — Located in the heart of Pasadena, but has a small farm feel. Enjoy a farmer's market, pumpkins, painting, hay games, local vendors, and live music on select dates.
Little Kid Fall Favorites
- Hansel Hill Farm & Orchard, Millersville — Hosting many kid-friendly fall and Halloween events and activities, including hayrides, orchard walks, marshmallow roasting, hands-on animal encounters, farm-themed crafts, pumpkins, and seasonal goodies.
- Homestead Gardens, Davidsonville — Fall Family Weekends are geared toward families with children ages 12 and under. Each weekend features tractor hayrides, pony rides, barnyard animals, hay mazes, pumpkin activities, bounce attractions, live music, food trucks, seasonal treats, and more.
Pumpkin Patches
- Clark's Elioak Farm, Ellicott City — This very kid-family friendly farm has a large pumpkin patch, petting farm, and enchanted forest.
- Knightongale Farm, Harwood — In addition to the pumpkin patch, the farm features a corn maze, hay rides, and pony rides.
Apple Orchards
- Larriland Farm, Woodbine — Known for its pick-your-own apples, the farm also offers handmade apple fritters, apple cider, and other homemade treats. Other farm highlights include hayrides, a maze, and boo barn.
- Weber's Cider Mill Farm, Parkville — Along with plenty of apples and apple delights, such as apple slushies and apple cider donuts, the farm has many family-friendly activities, such as hayrides, a hay maze, farm animals, a spooky skeleton walk.
🎃 Annapolis Fall & Halloween Events 2026: The Calendar
New events pop up here as soon as they're announced. No need to dig through a dozen Facebook groups. Just browse below!
Some events are weather-dependent — always double-check before you head out!
Know of an Annapolis Halloween event that should be listed? Submit it here.
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