Halloween is better when the candy comes to you! These community events let kids show off their costumes, collect candy, and enjoy festive fun all in one safe spot. From library parking lots to decorated tractors, Annapolis has plenty of options for families to enjoy this October.
Here’s your guide to local Trunk or Treats to make your spooky season extra sweet!
Blue Crab Cupcakes 4th Annual Trunk or Treat
Where: 1580 Whitehall Rd, Annapolis
When: Friday, October 24, 2025, 5:30–8 PM
Don’t miss Blue Crab Cupcakes’ 4th Annual Trunk or Treat! A sweet tradition for many Annapolis families! Kids can enjoy decorated trunks, fun games, and plenty of candy, while parents will love the live bands, food trucks, and festive atmosphere. This year’s eats include Jimmy’s Famous Seafood and Salt & Pepper BBQ Flipn’ Bowl. Add in costume contests, prizes, and of course, cupcakes, and you’ve got one of the most anticipated Halloween celebrations in town.
Glen Burnie Library’s Trunk or Treat
Where: Glen Burnie Library parking lot, 1010 Eastway, Glen Burnie
When: Wednesday, October 29, 2025, 4:00 PM – 6:00 PM
Books and candy come together at the Glen Burnie Library’s popular Trunk or Treat. Library staff and community partners decorate cars and tables for kids to explore while collecting treats. Families can also enjoy crafts, games, and plenty of festive spirit. Don’t forget to bring a canned good to donate to a local food pantry! Helping others while celebrating Halloween makes this event extra special.
Homestead Gardens’ Tractor Treat
Where: 743 W Central Ave, Davidsonville
When: Thursday, October 16, 2025, 4–7 PM (Rain date Oct 20)
Homestead Gardens puts a farm-fresh twist on trunk or treat with their annual Tractor Treat. Instead of cars, kids can trick-or-treat from decorated tractors and farm equipment lined up throughout the property. Families will also enjoy live music, face painting, barnyard animals, beer for the grown-ups, and food trucks serving fall favorites. Don’t forget to dress up! There’s a costume contest for children 12 and under. A $3 family donation supports local causes, making this a feel-good way to celebrate and a can’t miss event.
Howl-O-Ween Paw-Ty
Where: Anne Arundel Animal Services, 411 Maxwell Frye Rd, Millersville
When: Saturday, October 26, 2025, 10 AM–1 PM
If your kids love animals, this one’s for you! Anne Arundel Animal Services hosts a safe trick-or-treat trail alongside meet-and-greets with adoptable pets. Families can enjoy seasonal activities, learn about pet adoption, and celebrate Halloween with some furry friends. While not a traditional trunk or treat, it’s a fun (and heartwarming) way to add something different to your Halloween weekend.
Navy MWR Annapolis Trunk or Treat
Where: North Pool Pavilions (168 Bennion Rd, Annapolis)
When: Friday, October 24, 2025, 3:30–5:30 PM
Military families in Annapolis won’t want to miss this festive afternoon hosted by Navy MWR. The event is free and open to the community, with trunks packed full of candy, pumpkin decorating stations, and inflatables. Costumes are strongly encouraged, and kids will love exploring each creatively decorated trunk.
Pip Moyer Recreation Center’s Fall Harvest Festival & Trunk or Treat
Where: Pip Moyer Recreation Center, 273 Hilltop Lane, Annapolis
When: Saturday, October 25, 2025, 10 AM–2 PM
This family festival brings a full day of fall fun to Annapolis! Kids can train alongside their favorite superheroes, sing along with beloved Disney princesses, and take part in a variety of seasonal activities. Highlights include hayrides, a spooky magic show, a pumpkin patch, and of course, trunk-or-treating. With so much to see and do, this event is a perfect one-stop celebration for families looking to pack in maximum Halloween.
Severna Park Community Center’s Halloween Spooktacular
Where: Severna Park Community Center, 623 Baltimore Annapolis Blvd, Severna Park
When: Saturday, October 25, 2025, 5 PM–8 PM
This free community celebration is packed with family fun! Families can enjoy trunk-or-treating, children’s activities, crafts, a spooky photo booth, and even a dance performance. Popcorn, treats, local vendors, and food trucks will round out the evening, making it a festive way to spend Halloween weekend without leaving Severna Park.
Wildberry Farm + Lifestyle’s Halloween Field Market
Where: Wildberry Farm + Lifestyle, 1047 Saint Stephens Church Rd, Crownsville
When: Saturday, October 25, 2025, 9 AM–Noon
Celebrate Halloween farm-style with Wildberry Farm + Lifestyle’s outdoor market. Families can browse dozens of local small businesses, enjoy a hot breakfast and coffee from the Wildberry Farm to Table Food Trailer, and trick-or-treat the vendor booths in costume. Admission is free, and even leashed pups are welcome. With its mix of fall shopping and festive fun, this event is a charming way to start your Halloween weekend.
Tips for a Successful Trunk or Treat
- Bring a bag or bucket for candy.
- Dress in layers—it’s Maryland in October, after all!
- Arrive early if parking is limited.
- Pack a flashlight or glow sticks for extra visibility.
- Double-check event details on host websites or social media before heading out.
Whether you’re looking for decorated cars, candy-filled tractors, or a cupcake-themed celebration, Annapolis has something for every family this Halloween. Mark your calendars, grab your costumes, and enjoy a sweet (and spooky) October!
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