The information below is from 2019. To find 2020 holiday events or activities, check our Kids Calendar or Holiday Fun Guide.

The holidays are the pinnacle of many kids’ year. (At least in our house, “how many days until Christmas?” started about three months ago.) Throw into the mix some trains rides and boats, and your kids will be just about over the moon. Below you’ll find a collection of some of the area’s best holiday train and ship experiences. On many, Santa himself makes an appearance. On even more, so does hot chocolate. Let the holidays begin!


Holiday Express. The holidays don’t officially begin until that old steam whistle bleats out from Oaks Bottom. The Holiday Express train ride has all the fixins’ for a sweet, family-friendly ride. The train starts at Oaks Park and travels down Springwater Corridor toward OMSI before turning around, making for about a 45 minute trip. The interior of the train is decorated with holiday lights, friendly volunteers give information about the train, and Santa and his elves make a visit to each car to hand out candy canes.
Weekends November 29 through December 15.
All trains load at Oaks Station, 7805 SE Oaks Park Way, Portland OR
Tickets available for purchase online and range from $12 to $22 per ticket.

The Polar Express & Santa Steam Trains. If you want Polar Express, then Polar Express you shall have—though you’ll have to drive a wee bit farther. The Chehalis-Centralia Railroad and Museum in Washington offers a Polar Express ride featuring the reading of the popular book plus a visit from Santa, cocoa and cookies.
Polar Express: Fridays, Saturdays and Sundays November 22 – December 22.
Trains load at 1101 SW Sylvenus St., Chehalis WA
Tickets available for purchase online. $38 per ticket.

Chelatchie Prairie Railroad Christmas Tree Runs. Take a scenic trip through southwest Washington on a 1941 diesel train, purchase your Christmas tree, and get a visit from Santa! Riders will also be treated to warm cider and cocoa, hot coffee and cookies.
Weekends, November 30 through December 17.
Train loads at 207 N. Railroad Ave., Yacolt WA
Tickets available for purchase online and vary depending on the type of tree purchased and number of riders.

Cinnamon Bear Cruise. Cruise down the Willamette with a host of characters from the classic Cinnamon Bear radio show and book. The cruise is filled with special treats, from photos to the Cinnamon Bear, to story time with Queen Melissa, to candy plundering, to a magic show. Hot chocolate and other tasty treats abound.
Select days November 30 through December 27.
Boat boards at the Salmon Street Springs Dock, 1000 SW Naito Pkwy, Portland OR
Tickets available for purchase online and range from $15 to $43.

Christmas Ships. Now in its 65th season, the light-filled Christmas ships parade is a must-see. Check out their 2019 schedule to see where the best spots are to watch. Dress warm, brings a thermos, and enjoy the sights!
Select days December 5 through December 22 with Meet and Greet events December 21 and 22.

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