👻 Historic Ghost Tour
📍 Downtown Annapolis, MD
📅 Select dates Oct. 1–31, 2026
Follow a period-attired guide through Annapolis’ historic streets for four centuries of documented ghost stories, unexplained happenings, and spooky stops.
🧙 Annapolis Witches & Legends Walking Tour
📍 Downtown Annapolis, MD
📅 Select dates Oct. 4–30, 2026
Walk through Annapolis history while exploring Maryland’s witch trials, colonial superstitions, local legends, and the stories that still linger today.
🎃 The Great Annapolis Pumpkins
📍 Downtown Annapolis, MD
📅 Oct. 5–Nov. 2, 2026
A fall favorite bringing seasonal charm to downtown Annapolis with festive giant pumpkins, family fun, and autumn photo moments.
🪦 Very Superstitious! Paca House & Garden Tour
📍 William Paca House & Garden, Annapolis, MD
📅 Select dates Oct. 9–31, 2026
Explore the folklore, rituals, lucky charms, and everyday superstitions that shaped life in centuries past during this special historic house tour.
🌊 Halloween Paddle by CapitalSUP
📍 Downtown Annapolis, MD
📅 Oct. 31, 2026
Costumes on, paddles up! Take your Halloween spirit to Spa Creek for a spooktacular paddleboarding adventure.
🔮 Maryland Witches Pub Crawl
📍 Downtown Annapolis, MD
📅 Select dates Oct. 9–31, 2026
Sip your way through Annapolis while learning about Maryland’s witch trials, superstitions, accusations, and the women whose stories became local legends.
🦇 Bat Out of Helloween: Celebrating Meat Loaf and Rocky Horror
📍 Rams Head On Stage, Annapolis, MD
📅 Oct. 10, 2026
Turn up the volume for a spooky rock-and-roll night celebrating Meat Loaf, Rocky Horror, and other Halloween favorites.
🧙 Profs & Pints Annapolis: Ancient Terrors of the Night
📍 Graduate by Hilton Annapolis
📅 Oct. 13, 2026
Take a fascinating look at what terrified the ancient Greeks and Romans, from ghosts and demons to magic, supernatural beings, and the reanimated dead.
🕯️ Colonial Cocktails: Spirits with the Spirits
📍 Historic London Town & Gardens, Edgewater, MD
📅 Oct. 15, 2026
Sip colonial-inspired cocktails while hearing ghostly stories and learning about the All Hallows’ Eve traditions of the 18th century.
🍭 Trick or Treat Trail
📍 Downs Park, Pasadena, MD
📅 Oct. 17, 2026
Make your way along the park trails for kid-friendly trick-or-treating, with Halloween fun geared toward children ages 12 and under.
👻 Jug Bay Ghost Paddle
📍 Jug Bay Wetlands Sanctuary, Lothian, MD
📅 Oct. 17, 2026
Paddle along the Patuxent River as you watch for wildlife, hear local ghost stories around a campfire, and enjoy cider, dinner, s’mores, and popcorn.
🎭 The Legend of Sleepy Hollow by The Colonial Players of Annapolis
📍 Annapolis, MD
📅 Oct. 23–Nov. 8, 2026
Get swept up in a playful take on Washington Irving’s classic tale, complete with gossip, rivals, romance, superstition, and the legendary Headless Horseman.
👻 Annapolis Scarecrow Stroll
📍 Downtown Annapolis, MD
📅 Oct. 24–Nov. 2, 2026
Stroll through downtown Annapolis as creative scarecrows take over West Street, Maryland Avenue, and State Circle for this annual fall tradition.
🎻 Naptown Philharmonic Halloween Spooktacular
📍 St. John’s College, Annapolis, MD
📅 Oct. 25, 2026
Celebrate Halloween with classical and contemporary music, special guest artists, and a costume contest for all ages.
🧛 Candlelight: A Haunted Evening of Halloween Classics
📍 Maryland Hall, Annapolis, MD
📅 Oct. 29, 2026
Settle in under candlelight for a Halloween-inspired evening of music at Maryland Hall.
🧟 Halloween Whodunit 3: Comedy Murder Mystery
📍 Rams Head On Stage, Annapolis, MD
📅 Oct. 29, 2026
Help solve a hilarious Halloween murder mystery as the audience becomes part of an over-the-top horror movie casting call.
🎃 Pumpkin Walk at Hammond-Harwood House
📍 Hammond-Harwood House, Annapolis, MD
📅 Oct. 30, 2026
Bring the family for games, crafts, snacks, storytelling, face painting, a costume parade, and a peek into colonial superstitions.
🥀 Spooky Sapphic Speakeasy
📍 Eastport Democratic Club, Annapolis, MD
📅 Oct. 30, 2026
Come dressed to impress for a spooky night of dancing, conversation, and Halloween fun with the local sapphic community.
🪩 HALL-o-ween featuring MJ DEJAVU + Blonde Ambition
📍 The HALL at Live!, Hanover, MD
📅 Oct. 31, 2026
Party Halloween with Michael Jackson and Madonna tribute performances, costumes, throwback hits, and plenty of ’80s and ’90s energy.
🍺 Halloween Decades Bar Crawl
📍 Live! Casino & Hotel Maryland, Hanover, MD
📅 Oct. 31, 2026
Jump from the ’60s to the ’70s, ’80s, and ’00s as participating venues bring each decade to life with themed vibes, music, and photo ops.
☠️ Haunted Pub Crawls
📍 Downtown Annapolis, MD
📅 Select dates throughout October 2026
Hear ghost stories while visiting three haunted pubs and spooky stops throughout historic Annapolis.
