Portland,OR 97214

Making the Magic Happen
One Cruise at a Time

We have gone above and beyond to create a truly unique experience full of magic and mystery. Travel through time and memory with us as we follow the spirit of the holidays.

Choose A Date

Canceled for 2021

Cruise down the river

Two hours on board the Portland Spirit

Hunt for the Silver Star

An interactive adventure for children

cinnamon bear and friends

A holiday tradition for generations!
Cinnamon Bear Brings magic to life

Be the guests of honor on this two-hour cruise. Enjoy holiday treats while a cast of fanciful characters entertain you with storytelling, music and magic. Have your picture taken with the Cinnamon Bear himself atop his magical throne. Make this a holiday your child will remember forever.


Storytime with Queen Melissa

Queen Melissa will carry you away into the a land of mystery, magic, and adventure!

Coloring Stations

Grab some color and make some wonder, don’t forget to enter your kiddos into our coloring contest

Snack Buffet

Enjoy some light breakfast buffet, including fresh fruit, cereal, yogurt, hot chocolate, orange juice and milk.

Picture With Cinnamon Bear

Each child will recieve a picture with cinnamon bear.

Character Autographs

Children love getting autographs from all of their favorite characters.

Crazy Quilt Dragon

Journey to the magical forest with crazy quilt dragon!


With multiple songs and stories, enjoy singing along to some of your favorite Christmas songs, as well as some we have created just for you.

Search for Treasure

Stop by Captain Taffy, gain some boating knowledge and grab some treasure from his treasure chest!

Magical Entertainment

Magic and Christmas go hand in hand, we make sure that there is no lack of magic on board, sit back and let Jack Frost lead you on this magial journey.




*daytime rates
*price subject to change

  • 2-Hour Cruise
  • Adult Beverage Bar Available
  • Snack Buffet



*daytime rates
*price subject to change

  • 2-Hour Cruise
  • Picture With Cinnamon Bear
  • Cinnamon Bear Cookie
  • Snack Buffet

All 2021 cinnamon bear cruises cancelled
Stay tuned for details on the drive in show!

Book Drive-in Show


Don’t take our word for it – here’s what our guests say!

Again, another wonderful year (2016) on the Cinnamon Bear Cruise….this is our fourth year in a row.
Am so impressed with the service on board. Every employee goes up and beyond for each child. I am so amazed.
The captain even let my son, kaden, steer the ship!
Thank you again Portland Spirit!
See you next year!!!!!

Kim E

Oh, man, does my kid love the Cinnamon Bear cruise!

Lisa B

We took our 4yr old Granddaughter on the cruise. I couldn’t believe how exceptional all of the characters were on the cruise. They went above and beyond to make my Granddaughter have a wonderful time. She has always loved fairies and they were the nicest and most fun fairies that my Granddaughter ever saw. She had so much fun that by the end of the cruise when the characters lined up to say good bye with hugs, my Granddaughter went through the line 4 times. We are already planning on this being a regular Christmas event that we do every Christmas. Any one that wants to put some happiness in a child’s life you have to take your child on this cruise. I can’t express how grateful we are to the wonderful people that treated my Granddaughter with such love and kindness.

James O

What an enjoyable way to spend a day. It gets you right into the Christmas spirit. Whoever is under the Cinnamon Bear outfit is just adorable. The Cinnamon Bear made our kids feel so special. The food is very good, for both adults and children. While it may seem to be geared toward kids, groups of adults can enjoy the cruise just as much.

John D

We all old and young enjoyed this new Christmas adventure. It was well done and even the weather cooperated . Will look forward to next year!

Le’Ann M

Check out all of our other holiday cruise options!

Portland Spirit Website

Find out more information about the Portland Spirit boat!

Vessel Features

Learn more information about our company and what we do!

About Us
ican radio logo

Cinnamon Bear on the Radio!

Join Judy, Jimmy and Santa’s right-hand man, Paddy O’Cinnamon, at noon and an encore broadcast each day at 6pm on icanradio.org and All Classical Portland’s HD2 channels.

The International Children’s Arts Network (ICAN) is a radio service, the first of its kind in the nation, available on All Classical Portland’s HD-2 channel and online worldwide via icanradio.org. ICAN’s goal is to provide greater access to arts and culture programming for young listeners and their families. During the month of December, ICAN is celebrating winter by airing heartwarming stories, poems, and music. Learn about the Winter Solstice, Saint Lucia’s Day, Hanukkah, Kwanzaa and traditions from around the world while enjoying Holiday favorites like the Nutcracker and classic carols. Kicking off the holiday season ICAN is airing the cherished radio series Cinnamon Bear every day starting December 1st until Christmas day.

Meet Some of the Cast!

With 17 Costumed Characters, there is a sure to be something for every child to enjoy.

The Cinnamon Bear

the star of the show

Queen Melissa

Crazy Quilt Dragon

Never say boo

Captain Taffy

he’s got a treasure chest


favorite color: purple


favorite color: green


favorite color: red


favorite color: blue

Nicky Froodle


the bartender

Peppermint Patty


favorite color: pink

Book Today

book online or call 503-224-3900


Cinnamon Bear History

The “Cinnamon Bear” began his life in 1937 as a holiday radio program written by Glanville and Elizabeth Heisch. This 26 chapter series ran from Thanksgiving through Christmas and still airs today on K103FM from 7:00-7:15pm.
The story follows Jimmy and Judy Barton as they search for the Silver Star for the top of their Christmas tree. The Cinnamon Bear takes them to Maybeland for their search. It seems the Crazy Quilt Dragon stole the star and ran off with it. On their journey they encounter a roster of enchanting characters.

The Cinnamon Bear made live appearances at Lipman Wolfe depart- ment stores from the 1940’s-1980’s just like Santa Claus. In fact, many children of Portland wrote their letters to Cinnamon Bear. The biggest prize in meeting the Cinnamon Bear in person was the cinnamon cookie. In the 1950’s, Lipman’s presented Cinnamon Bear Breakfasts that were aimed at children and were musical performances.

Today the Cinnamon Bear makes appearances on the Portland Spirit along with his entire cast of friends that runs throughout the month of December. The Portland Spirit has even put together a picture book depicting the adventure along with a line of products that children can take home to make this tradition a part of their family!

Cinnamon Bear History
cinnamon bear historical patch