Portland Spirit Keeps a Holiday Tradition Afloat

Two decades ago, Portland Spirit had a radical idea: What if we bring back the Cinnamon Bear, Portland’s slightly creepy-but-endearing holiday mascot?  The Cinnamon Bear story, originally broadcast in 1937 as a national radio production, became a cherished local tradition when Lipman & Wolfe department store adopted the lovable bear as its Christmas mascot. For decades, meeting Cinnamon Bear was among Portland families’ favorite holiday rituals until the early 1990s, when the character disappeared from the holiday scene. Today, children are once again lining up to meet Cinnamon Bear. This time aboard a boat. Portland Spirit revived this iconic holiday figure in 2005. Now, in 2025, the Cinnamon Bear Cruise celebrates its 20th year anniversary, continuing a beloved local tradition that has delighted thousands of families and rekindled childhood memories for parents and grandparents who once met the bear themselves as children. “We’re honored to keep this Portland legacy alive, especially for those parents and grandparents who grew up with Cinnamon Bear and want to share the beloved story with their grandkids,” said Dennis Corwin, General Manager of the Portland Spirit. “Cinnamon Bear isn’t just a holiday cruise, it’s a bridge between generations.”

The Cinnamon Bear story began in 1937 as a holiday radio serial created by Glanville and Elizabeth Heisch. Portlanders first met the bear through a 26-episode program that aired between Thanksgiving and Christmas. Lipman & Wolfe department stores later brought the character to life in-store, complete with photo sessions and cinnamon bear cookies. In the 1950s, Lipman’s introduced Cinnamon Bear Breakfasts, featuring musical performances.

Frederick & Nelson continued the tradition when it acquired Lipman’s in 1979, until the company’s last Oregon location closed in 1991. Just over two decades later, Portland Spirit acquired the rights to produce Cinnamon Bear cruises, reviving the character for a new generation. The inaugural cruise took place in 2005 and was met with great success, with many cruises selling out. The first cruise featured only Cinnamon Bear, but over time more Maybeland characters were introduced, including Queen Melissa, Captain Taffy, Crazy Quilt Dragon, and Jack Frost. Local composer Rick Lewis produced five original songs for the cruise, and Portland Spirit even published a children’s picture book, along with a range of themed merchandise available for sales online and onboard during the cruises.

The cruise took a two-year hiatus in 2020 and 2021 due to the pandemic — though Cinnamon Bear continued in a smaller capacity as part of an outdoor drive-through show at Oaks Park. Portland Spirit brought the cruise back in 2022 with a reimagined format. Today’s Cinnamon Bear Breakfast Cruise features reserved seating and a plated hot breakfast, replacing the previous general-admission seating and light continental breakfast. Guests can also look forward to:

• Story time with Queen Melissa

• A live magic show with Jack Frost

• A printed souvenir photo with Cinnamon Bear for every child

• A cinnamon bear cookie for all youth, a nod to Lipman’s original tradition

• Character meet-and-greets and photo opportunities throughout the cruise

The enchanting Cinnamon Bear tale follows Jimmy and Judy Barton on their quest to find the Silver Star for the top of their Christmas tree. Guided by Cinnamon Bear, they travel to Maybeland and encounter a host of charming characters, including the mischievous Crazy Quilt Dragon, who has stolen the star.

The Dates for the cruise are November 29–30, December 6–7, 13–14, 20–24, and 26–27.Boarding Time is 9:00 a.m. at Salmon Springs Dock, 1010 SW Naito Pkwy, Portland, OR 97204 Tickets start at $70 for adults, $50 for children (12 and under), and $15 for babies (includes souvenir photo). Reservations are available at portlandspirit.com/cinnamonbear or by calling 503-224-3900.

Portland Spirit operates a fleet of four boats, including the Explorer Jetboat, and offers a variety of cruises year-round including brunch, lunch, dinner, sightseeing and holiday cruises for both public and private events. The yachts have been equipped with an onboard galley to offer freshly prepared Northwest cuisine on cruises in addition to the ever-changing views. The company has been locally family owned and operated since 1994. For more information, visit portlandspirit.com.