From family-friendly pumpkin walks and tote-bag crafts to candlelit concerts, ghost tours, and even a witches’ pub crawl, there’s no shortage of ways to celebrate. We rounded up the best Halloween events around town so you can plan your October — costumes encouraged.
👻 Check back often — we’ll keep updating as more events pop up.
👪 = Family-friendly event
🍸= Adults only
🧒 = Made for kids
Bountiful Harvest
📍 Parole | 🍸 | $125–$175
📅 Friday, October 24 | 7–11 PM
This farm-to-table feast brings together the flavors of the season with cocktails, live entertainment, and plenty of fall charm. Guests will enjoy an elegant evening while supporting local causes — the perfect mix of giving back and living it up.
Annapolis Ghost Tours
📍 Downtown Annapolis | 👪 | $20 adults, $15 ages 5+
📅 Evenings, all October
Take a lantern-lit walk through Annapolis’s shadowy past. These guided ghost tours mix history with hauntings, sharing stories of restless spirits, old taverns, and legends that linger long after dark. Perfect for families with brave kids or anyone who loves a good chill.
Haunted Harbour Day
📍 Annapolis Harbour Center | 👪 | Free
📅 Saturday, October 25 | 10 AM–12:30 PM
A Halloween morning full of family fun! Kids can trick-or-treat around the shops, show off their costumes, and enjoy games and activities throughout the center. A perfect way to kick off Halloween weekend without keeping the little ones up past bedtime.
Halloween Spooktacular
📍 St. John’s College | 👪 | $30 adults, $10 kids
📅 Sunday, October 19 | 3–5 PM
The Naptown Philharmonic Orchestra sets the stage for a spirited afternoon of spooky tunes and family fun. Costumes are welcome, the music is magical, and it’s the perfect way to get into the Halloween mood together.
Glamityville II: Oh the Horror!
📍 Arts District | 🍸 | $20–$40
📅 Saturday, October 11 | 7–11 PM
Art, fashion, and fright collide at ArtFarm’s spookiest night of the year. Glamityville returns with costumes, creativity, and plenty of eerie energy. Expect a mix of high style and horror that’s anything but ordinary.
Tractor Treat 2025
📍 Davidsonville | 👪 | $3 per family
📅 Thursday, October 16 | 4–7 PM
Homestead Gardens is turning tractors into trick-or-treat stations! Families can enjoy decorated tractors, barnyard animals, live music, a kids’ costume contest, and plenty of fall fun. Proceeds benefit local youth agriculture programs, so it’s Halloween with a purpose.
Pumpkin Walk
📍 Downtown Annapolis | 👪 | $20–$25 per family
📅 Friday, October 24 | 4–6 PM
Take a spooky stroll through the Hammond-Harwood House with games, crafts, snacks, and a costume parade led by Frolic the Fox. Families can also enjoy storytelling, face painting, and a peek into colonial-era superstitions.
Halloween Spooktacular Trunk or Treat
📍 Severna Park | 👪 | Free
📅 Friday, October 24 | 5–8 PM
Severna Park Community Center is back with its 4th annual trunk-or-treat! Decorated cars, creative costumes, and plenty of candy make this a can’t-miss family night of Halloween fun.
Wildberry Farm Market Trick-or-Treat
📍 Crownsville | 👪 | Free
📅 Saturday, October 25 | 9 AM–12 PM
Bring the kids (and even the dog) for a morning of costumes, candy, and shopping local. Wildberry’s farm market will have dozens of vendors, plus hot breakfast and coffee from their food trailer.
Create Your Own Trick-or-Treat Tote Bags
📍 West Street | 🧒 | Free
📅 Saturday, October 25 | 10:30–11:30 AM
Kids ages 6–10 can design and decorate their very own Halloween tote bags to take home—just in time for trick-or-treating night. Supplies are provided, creativity required.
Candlelight: A Haunted Evening of Halloween Classics
📍 Maryland Hall | 👪 | From $36, Ages 8+
📅 Thursday, October 30 | 8:45 PM
Experience a spine-tingling string quartet by candlelight with music from Thriller to The Nightmare Before Christmas. A hauntingly beautiful way to spend Halloween week.
Witches of Maryland Walking Tour
📍 Downtown Annapolis | 👪 | $25 adults, $20 ages 5+
📅 Wednesday, October 8 & Wednesday, October 22 | 7 PM
Step back into Annapolis’s witch trial past on this 90-minute walking tour. Hear stories of superstition, fear, and resilience while strolling the city’s haunted streets. Witchy costumes encouraged.
Pumpkin Patch for a Purpose
📍 Forest Drive | 👪 | Free entry
📅 Thursdays & Fridays, 2–6 PM | Saturdays & Sundays, 10 AM–6 PM | September 27–October 31
Pick out the perfect pumpkin and support The Light House, Annapolis’s homeless prevention and support center. Games, photo ops, and pumpkins for a cause all season long.
