Costumes? Check. Candy buckets? Check. A calendar full of spooky fun? We’ve got you covered!
Halloween is almost here, and Annapolis and the surrounding area are packed with ways to celebrate. From trick-or-treating and costume contests to monster mashes and cocktails for the grown-ups, there’s something for every little ghost, goblin and grown-up ghoul.
Get those costumes ready and check out these Halloween celebrations you won’t want to miss!
Halloween Scavenger Hunt & Costume Contest
Oct. 17 | 9-11 a.m. | Downs Park, Pasadena
Start your Halloween festivities with a scavenger hunt through the trails at Downs Park! Follow the clues to the decorated amphitheater rooms, then show off your best Halloween look in a costume contest. The event takes place rain or shine. Registration is required by emailing Ranger Carter at rpcart24@aacounty.org.
Monsters on Main Street
Oct. 17 | 1-3 p.m. | Main Street at South River Colony, Edgewater
Calling all little monsters! Dress up your ghosts, goblins, superheroes and princesses for an afternoon of trick-or-treating along Main Street in Edgewater. Stop by participating businesses to collect treats, then spin the prize wheel for a chance to win. It’s a fun way to celebrate Halloween while exploring local shops.
Halloween Spooktacular
Oct. 23 | 5-8 p.m. | Severna Park Community Center, Severna Park | Free
Grab your favorite costume and head to the Severna Park Community Center for an evening of Halloween fun! This free community celebration features games, crafts, treats, entertainment and spooky surprises for the whole family. Bring the kids, invite the neighbors and get ready for a frightfully fun night.
Bountiful Harvest: Costumes & Cocktails
Oct. 23 | 7-11 p.m. | The Atreeum at Soaring Timbers, Annapolis | $150-$200
Who says Halloween is just for kids? Trade the trick-or-treat buckets for cocktails at this adults-only fundraising celebration. Enjoy an open bar, gourmet food, silent and live auctions, and an evening out for a good cause. It’s an opportunity to enjoy a festive night out while supporting the community.
3rd Annual Halloween Dance
Oct. 23 | 7–10 p.m. | Unity by the Bay, Annapolis
Get ready to boo-gie the night away! Dress in your Halloween best for an evening of dancing, music, costume contests and raffles. Monster munchies and witches’ brew will be available for purchase, making this a fun option for a festive night out with friends.
Haunted Harbour Day
Oct. 24 | 10 a.m.-12:30 p.m. | Annapolis Harbour Center, Annapolis | Free
Annapolis Harbour Center is turning up the Halloween fun with a morning of treats and activities! Kids can trick-or-treat throughout the shopping center, decorate pumpkins, get glitter tattoos and enjoy balloon art. There’s also free popcorn, prizes and a children’s costume contest from 11:30 a.m. to 12:30 p.m. Bonus: Kids receive a free trick-or-treat bag!
Howl-O-Ween Party
Oct. 24 | 10 a.m.-1 p.m. | Anne Arundel County Animal Services, Millersville
Calling all animal lovers! Anne Arundel County Animal Services is hosting its 12th annual Howl-O-Ween Party, complete with games, goodies and a trick-or-treat trail through the woods. Kids can also visit the “Candy with a Cop” police vehicles and adopt a toy pet from the Friends of Anne Arundel County Animals table. Plus, there will be adorable shelter animals looking for forever homes!
Trick or Treat Trail
Oct. 24 | Noon-4 p.m. | SPCA of Anne Arundel County, Annapolis | Free-$5
Take your Halloween celebration into the woods at the SPCA’s Trick or Treat Trail! The wooded paths will be transformed into a family-friendly Halloween experience, perfect for kids who love a little spooky adventure. Even your four-legged family members can join the fun because the trail is dog-friendly!
Halloween Spooktacular
Oct. 25 | 3-5 p.m. | St. John’s College, Annapolis
Halloween meets live music at this family-friendly concert presented by the Naptown Philharmonic Orchestra! Enjoy a mix of classical and contemporary music designed with young audiences in mind. Come dressed in costume for a chance to win prizes in the all-ages costume contest.
Coffee, Crafts & Cruisers Monster Mash
Oct. 26 | 10 a.m.-noon | Skate Zone, Odenton | $8
A Halloween party for the littlest monsters? Yes, please! Kids ages 10 and younger can dress up for a costume parade, join a candy scramble and make a Halloween-themed craft. Strollers and plastic ride-on toys are welcome, and parents get free coffee while the kids have fun. Admission includes skate rental, and spectating parents get in free.
Graveyard Groove Adults-Only Halloween Bash
Oct. 30 | 8–11 p.m. | Pip Moyer Recreation Center, Annapolis | Free
Who says the kids get to have all the Halloween fun? Leave the little monsters at home and head to this adults-only Halloween bash featuring live music, costume contests, games, tarot and palm readers, refreshments and more. Best of all, it’s free!
Spooky Sapphic Speakeasy
Oct. 30 | 6–10 p.m. | Eastport Democratic Club, Annapolis | $26
Grab your best costume and get ready for a spooky night of dancing, conversation and community! Hosted as part of Annapolis Pride’s events, this Halloween celebration brings locals together for an evening of music, fun and connection.
Day of the Dead Festival (Día de los Muertos)
Oct. 31 | 3-8 p.m. | Maryland Hall, Annapolis | Free
Celebrate Día de los Muertos with an afternoon and evening of music, art and tradition! This annual cultural celebration features live music, traditional dance, altars, food and family-friendly activities. It’s a wonderful opportunity to learn about the traditions of Día de los Muertos while honoring loved ones and celebrating the community.
HALL-o-ween Featuring MJ DEJAVU + Blonde Ambition
Oct. 31 | The HALL at Live!, Hanover
Halloween meets the ultimate throwback party! Break out your best costume and get ready for a night celebrating Michael Jackson and Madonna, complete with tribute performances and plenty of ’80s and ’90s hits. Perfect for anyone whose ideal Halloween party involves singing and dancing to the classics.
6th Annual Halloween Bash
Oct. 31 | 9–11 p.m. | Rod ‘N’ Reel Resort, Chesapeake Beach | Free | Ages 21+
Ready for a Halloween night out without the kids? Head to the 1936 Bar & Grill for an adults-only party featuring a costume contest with prizes, specialty Halloween cocktails, late-night food and music. Costumes are encouraged but not required, and free registration is available to help the venue plan.
Whether you’re collecting candy with the kids, enjoying a night out with friends or celebrating Día de los Muertos, there’s no shortage of ways to make Halloween memorable this year. So dust off those costumes, grab your boo crew and get ready for some spooky fun!
Looking for more Halloween activities? Check out the Annapolis Moms events calendar for even more local happenings. In case you missed it, check out our Trunk or Treat guide.
The Real Mom Recap | Oct. 12, 2026