The Cinnamon Bear

The Cinnamon Bear

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Paddy O' Cinnamon & pals will sail to Maybeland aboard the Portland Spirit starting this November!

Join Cinnamon Bear and his friends from Maybeland as they return to spread holiday cheer this season. The whole family will enjoy reserved seating and a plated breakfast while a cast of fanciful characters entertains the kids with storytelling, music and magic. Tickets include a printed souvenir picture with Cinnamon Bear atop his magical throne, and much more. Cinnamon Bear has been a holiday tradition for generations and you’re invited to make this season one your child will remember forever.

Photos from The Cinnamon Bear's post 03/07/2026

I have crossed the Maybeland mountains. I have faced the Crazy Quilt Dragon. And NOW… I put on bunny ears. 🐻🐰

Worth it. Because Easter Sunday on the Portland Spirit means brunch, mimosas, live piano, and river views — and I, Cinnamon Bear, ahem, Cinnabunny, will be there in the fur.

April 5, 2026 | Two cruises: 10 AM & 2:30 PM

See you there. ⚓🌸

01/01/2026

Thanks for a great season! See you next year for our 21st anniversary of Cinnamon Bear Cruises! 👋🐻

12/26/2025

Last two days! 🥹

Photos from The Cinnamon Bear's post 12/23/2025

POV: When morning cruises look like sunset cruises. 🥰

Photos from The Cinnamon Bear's post 12/21/2025

You might not recognize them without their signature white suits, but we had royalty on the boat yesterday. Prime Minister Ron Fisher of the Royal Rosarians.

Photos from The Cinnamon Bear's post 12/18/2025

🎄✨ Did You Know? The Cinnamon Bear Has Been Spreading Holiday Magic Since 1937! ✨🎄

The beloved Cinnamon Bear began his journey in 1937 as a holiday radio series written by Glanville and Elizabeth Heisch. This 26-chapter adventure aired from Thanksgiving through Christmas and quickly became a cherished tradition where families gathered around the radio each day to count down to Christmas together.

Here in Portland, Lipman-Wolfe’s sponsored the broadcasts, and from the 1940s through the 1980s, the Cinnamon Bear made his home in their stores each holiday season, just like Santa Claus. 🎅 Kids even wrote letters to the Cinnamon Bear, and the ultimate reward for meeting him in person? A famous cinnamon cookie. In the 1950s, Lipman’s hosted Cinnamon Bear Breakfasts featuring music and performances just for children.

✨ Today, the tradition lives on! Cinnamon Bear and his full cast of friends now appear aboard the Portland Spirit, now in its 20th year of cruises. They’ve even created a Cinnamon Bear picture book and a line of souvenirs that families can take home so this timeless holiday tradition can become part of your family story. too. ❤️

🎶🐻 A little nostalgia, a lot of magic, and a holiday tradition that continues to warm hearts generation after generation.

12/16/2025

🐻✨ We're coming up on our final week of Cinnamon Bear Breakfast Cruises! ✨🐻

Starting this Saturday, the cruise will run daily through December 27 (except Christmas Day). Don’t miss your final chance to celebrate the 20th anniversary of this beloved holiday tradition!

12/02/2025

Set sail with us on KOIN 6! 🚢💬 Catch my "chat" with Nicole DeCosta and GM Dennis Corwin!

Photos from The Cinnamon Bear's post 11/25/2025

The magic begins this weekend! 🐻✨

11/23/2025

"What do you do when you hear 6️⃣7️⃣ Cinnamon Bear?"

Portland Spirit marks 20 years of Cinnamon Bears Cruises on the Willamette 11/19/2025

Did you catch my debut on AM Extra? 🐻🎬

Portland Spirit marks 20 years of Cinnamon Bears Cruises on the Willamette Portland Spirit marks 20 years of Cinnamon Bears Cruises on the Willamette

11/13/2025

The original trendy bear! 🐻

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