by Annapolis, Maryland — Halloween 2026 is bringing a mix of family-friendly celebrations, historic ghost tours, pumpkin displays and spooky seasonal entertainment to Maryland’s capital. From downtown Annapolis to nearby communities across Anne Arundel County, residents can find activities for children, families and adults in the days leading up to October 31.
With Halloween falling on Saturday, October 31, 2026, families have a full weekend to enjoy costumes, candy, autumn attractions and local traditions. Several events are scheduled for the final week of October, making it a good time to plan outings and check registration details in advance.
1. The Great Annapolis Pumpkins
The Great Annapolis Pumpkins is a seasonal attraction bringing oversized pumpkins and autumn-themed photo opportunities to downtown Annapolis. Families can enjoy the festive displays while exploring local shops, restaurants and historic streets.
The 2026 display is scheduled to run from October 5 through November 2, giving visitors time to enjoy the pumpkins even after Halloween night. It is a suitable option for families looking for a relaxed fall outing rather than a traditional haunted attraction.
2. Historic Ghost Tours in Downtown Annapolis
Annapolis is known for its historic buildings, colonial-era streets and centuries of local stories. During October, guided ghost tours introduce visitors to the city’s darker history, unexplained tales and reported supernatural encounters.
Historic Ghost Tours are scheduled on select dates through October 31, 2026. Visitors can explore downtown on foot with a guide while learning about historical locations and local legends.
These tours may appeal particularly to adults, couples and older teenagers looking for a spooky evening activity. Guests should check age recommendations, departure times and ticket availability before attending.
3. Annapolis Witches and Legends Walking Tour
For visitors interested in folklore and Maryland history, the Annapolis Witches and Legends Walking Tour offers another way to explore the city’s past.
The tour covers stories associated with witch trials, colonial superstitions and local legends. It is scheduled on select dates through October 30, 2026, making it an option for those planning an outing before Halloween night.
The walking format allows visitors to experience the historic downtown atmosphere while hearing stories connected to the region’s past. Comfortable shoes and weather-appropriate clothing are recommended for an outdoor evening tour.
4. The Legend of Sleepy Hollow
The Colonial Players of Annapolis are presenting The Legend of Sleepy Hollow, a theatrical adaptation of Washington Irving’s classic tale featuring the legendary Headless Horseman.
The production is scheduled to run from October 23 through November 8, 2026. The story combines mystery, superstition, romance and spooky characters, making it a seasonal entertainment option for theatre fans.
Visitors planning to attend should check the performance calendar for available dates and showtimes. Because the production continues beyond Halloween, it may also suit families and visitors who want a Halloween-themed activity in early November.
5. Halloween Pumpkin Walk at Hammond-Harwood House
The Pumpkin Walk at Hammond-Harwood House is scheduled for Friday, October 30, 2026, offering families a chance to enjoy Halloween activities in a historic setting.
The event is expected to include games, crafts, snacks, storytelling, face painting and a costume parade. The programme also introduces visitors to colonial-era superstitions, connecting traditional Halloween fun with local history.
Parents looking for an activity before Halloween Saturday may want to consider this event. Families should confirm admission details and the latest schedule before setting out.
6. Halloween Whodunit 3: Comedy Murder Mystery
For adults who prefer comedy mixed with Halloween suspense, Halloween Whodunit 3 is scheduled at Rams Head On Stage on Thursday, October 29, 2026.
The show uses a murder-mystery format with humorous twists and a horror-movie-inspired setting. Audience members can enjoy the unfolding mystery while following the clues and characters.
This event may be a good choice for a Halloween date night or an evening out with friends. Check the event’s ticket availability, age guidance and starting time before attending.
7. Candlelight: A Haunted Evening of Halloween Classics
Music lovers can look forward to Candlelight: A Haunted Evening of Halloween Classics, scheduled for October 29, 2026, at Maryland Hall in Annapolis.
The Halloween-themed concert offers a different kind of seasonal entertainment, combining atmospheric candlelight with music suited to the spooky season.
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It may appeal to couples, music enthusiasts and visitors who want a quieter alternative to haunted houses or crowded Halloween parties. Attendees should confirm the concert’s start time and ticket arrangements before making plans.
8. Annapolis Scarecrow Stroll
The Annapolis Scarecrow Stroll is another autumn attraction for people exploring the city’s historic downtown. Creative scarecrow displays are scheduled to appear around West Street, Maryland Avenue and State Circle.
The 2026 event runs from October 24 through November 2, offering opportunities to view the displays during the final week of October and immediately after Halloween.
Families can make the stroll part of a downtown outing, take seasonal photographs and explore nearby businesses. The outdoor format also makes it a flexible option for visitors who prefer to plan their own route and pace.
Which Halloween event in Annapolis would you most like to attend this year? Share your favourite seasonal activity or Halloween plans in the comments.
