Meet the classic holiday characters with a history dating back nearly 90 years!
Looking for a magical holiday experience the whole family will love? This holiday season, set sail to Maybeland aboard Portland Spirit’s Cinnamon Bear Breakfast Cruise! Perfect for families with young children, this two-hour holiday cruise combines a plated breakfast, reserved family seating, and plenty of holiday magic. Kids can meet the beloved Cinnamon Bear, enjoy storytime with Queen Melissa, collect autographs, and be amazed by Jack Frost’s live magic show, all while taking in views of Portland from the river.
Whether you’re continuing a family tradition or introducing your little ones to Cinnamon Bear for the first time, this special holiday outing offers a memorable way to celebrate the season together.
A Beloved Holiday Tradition Since 1937
Cinnamon Bear has been enchanting children for generations. The character first appeared in 1937 in a 26-chapter holiday radio program written by Glanville and Elizabeth Heisch.
The original series became a seasonal ritual for families, who tuned in between Thanksgiving and Christmas to follow Cinnamon Bear’s adventures and count down the days until Christmas. The character eventually became a beloved holiday fixture in Portland, appearing at Lipman and Wolfe department stores from the 1940s through the 1980s.
Just like visits with Santa, meeting Cinnamon Bear became a cherished childhood memory for many local families. Children even wrote letters to Cinnamon Bear.
Today, that sweet tradition continues aboard the Portland Spirit. For parents and grandparents who remember Cinnamon Bear from their own childhoods, the cruise is an opportunity to share a little holiday nostalgia with the next generation.
Cinnamon Bear Cruise Details for 2026
Cruise Dates: November 28-29, December 5-6, 12-13, 19-22, 23-24, 26-27
Schedule: Boarding begins at 9 am, and the cruise sails from 9:30 to 11:30 am.
Departure location: Salmon Springs Dock, 1010 SW Naito Parkway, Portland, Oregon.
Ticket prices: Starting at $72 for adults, $52 for children age 12 and younger, and $15 for infants. Tickets include the two-hour Willamette River cruise, plated hot breakfast, coffee/tea, hot cocoa, reserved table seating, onboard entertainment, a souvenir photo and cinnamon bear treat for each child age 12 and younger, and service gratuity.
Ready to set sail for Maybeland? Visit portlandspirit.com/cinnamonbear to explore dates and reserve your family’s seats, or call 503-224-3900.
