Annapolis Halloween Events

Candlelight: A Haunted Evening of Halloween Classics

Maryland Hall 29 Oct 2026

Haunted Harbour Day 2026

2512 Solomons Island Rd, Annapolis, MD 21401, United States 24 Oct 2026

Halloween Whodunit 3 at Rams Head On Stage

Rams Head On Stage 29 Oct 2026

AACSPCA's Trick or Treat Trail

SPCA of Anne Arundel County 24 Oct 2026

AACSPCA's Forest of Fear

SPCA of Anne Arundel County 23 Oct 2026

HAUNTED THRIFT STORE PAINT NIGHT with Artagayne at Art Farm

Art Farm Studios 29 Oct 2026

Bountiful Harvest - Costumes & Cocktails

10 Hudson St, Annapolis, MD, United States, Maryland 21401 23 Oct 2026

Fall Fest

Alder Rd, Annapolis, MD 21402, United States 23 Oct 2026

Annapolis - Oct 22/23/24 - Edgar Allan Poe Speakeasy

730 Bestgate Rd, Annapolis, MD 21401-2137, United States 24 Oct 2026

Le Petit Masquerade @ Rumhouse (Caribbean Fine Dining - Annapolis)

Rumhouse 31 Oct 2026

Halloween Spooktacular!

St. John's College 25 Oct 2026

Tavern Talk: Inside Annapolis’s Revolutionary-Era Taverns

43 Pinkney St, Annapolis, MD 21401-1717, United States 31 Oct 2026

The Legend of Sleepy Hollow

108 East St, Annapolis, MD, United States, Maryland 21401 23 Oct 2026

What the Trees Know: A Fall Sound Bath for What You're Ready to Release

333 Dubois Rd 30 Oct 2026

Arcade Live

Annapolis Market House 31 Oct 2026

MON 10/12 – SAT 10/17: Third Eye Thriller

209 Chinquapin Round Rd, Annapolis, MD, United States, Maryland 21401 12 Oct 2026

Trick-Or-Treat at Ridge Grow

244 Old Mill Bottom Rd S, Annapolis, MD 24 Oct 2026

Trunk or Treat

2525 Riva Rd 27 Oct 2026

Tri-Ward Trunk or Treat

The Church of Jesus Christ of Latter-day Saints 27 Oct 2026

Seventh Annual Freaky Flotilla- Halloween Social Paddle

Truxtun Park Rd, Annapolis, MD 21403 31 Oct 2026

Fiesta de Halloween.

The Church of Jesus Christ of Latter-day Saints 24 Oct 2026

Tartan Terrors at Rams Head On Stage

Rams Head On Stage 17 Dec 2026