Fall Cruises & Haunted Walking Tours

Upcoming cruises, walking tours & special events at Watermark in Annapolis

Explore Fall Experiences

Choose from hundreds of cruises, walking tours, ghost tours and special events in October, November and December. With experiences offered in Annapolis and Baltimore, Watermark makes it easy to find a memorable way to enjoy the season.

Browse our upcoming cruises, walking tours, ghost tours and special events to find the perfect Watermark journey. Many seasonal experiences offered on select dates, so reserve your tickets early.

Public Cruise

Annapolis, MD

• Dates: Saturday May - October

• Departure: Annapolis, MD

• Duration: 1 hour 30 minutes

Full Day Event

Annapolis - St. Michaels

• Dates: November 7, 2026

• Departure: Annapolis - St. Michaels

• Duration: 7 hour 30 min

Walking Tour

Annapolis, MD

• Dates: Second Saturday of Month

• Departure: Annapolis, MD

• Duration: 90 min

Public Cruise

Annapolis, MD

• Dates: Select dates

• Departure: Annapolis, MD

• Duration: Coming soon

Public Cruise

Baltimore, MD

• Dates: December 2026

• Departure: Baltimore, MD

• Duration: Coming Soon

Special Event

Baltimore, MD

• Dates: December 31, 2026

• Departure: Baltimore, MD

• Duration: Coming soon

Walking Tour

Annapolis, MD

• Dates: Returns Winter 2026

• Departure: Annapolis, MD

• Duration: Coming soon

Walking Tour

Annapolis, MD

• Dates: Holiday season

• Departure: Annapolis, MD

• Duration: 1 hour 45 min

Walking Tour

Annapolis, MD

• Dates: Holiday season

• Departure: Annapolis, MD

• Duration: 1 hour 30 minutes

Public Cruise

Annapolis, MD

• Dates: Holiday season

• Departure: Annapolis, MD

• Duration: 40 min