Holiday Trains and Ships Near Portland, OR

The holidays are the pinnacle of many kids’ year. 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!

This post is generously sponsored by Bridgeport Village. Don’t miss their holiday happenings, including visits with Santa, Mrs. Claus story times, live music, celebrations, and more! Bridgeport Village is busy putting the finishing touches on an extensive refresh, leaving no detail to chance as the successful shopping and lifestyle center prepares for the busy holiday season. Radiating from a new, park-like Village Green, a well-curated assortment of retailers, family-friendly restaurants and entertainment options stand ready to impress guests of all ages. Bridgeport Village is a reimagined four-season destination, artfully blending shopping, dining, and discovery. Rediscover Bridgeport Village!

Cinnamon Bear Breakfast Cruise

For generations, families have been sharing breakfast and listening to magical character story time on board the Portland Spirit. Find out what all the fuss is about, if you haven’t experienced the magic yet.
When: Nov. 25-26 & Dec. 2-3, 9-10, 16-17, 22-24, 26-27, 2023
Where: Portland Spirit
Cost: $49/child, $66/adult, includes food, drink, performances, photo with Cinnamon Bear and more. Book here.

Holiday Express

The holidays don’t officially begin until that old steam whistle bleats out from the Oregon Rail Heritage Center. The Holiday Express train ride has all the fixins’ for a sweet, family-friendly ride. The train starts at the Oregon Rail Heritage Center and travels down the Springwater Corridor toward Oaks Park 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.
When: Weekends, November 24 through December 17, 2023.
Where: All trains load at the Oregon Rail Heritage Center, 2250 SE Water Ave., Portland OR
Cost: $25/child, $31/adult, $99/family. Book here.

Chelatchie Prairie Railroad Christmas Special Train

Take a scenic trip through southwest Washington on a 1941 diesel train, and get a visit and a gift from Santa. Plus an ugly sweater contest and hot beverages! Please note, no trees for purchase this year.
When: Weekends, November 25 through December 17, 2023.
Where: Train loads at 207 N. Railroad Ave., Yacolt ,WA
Cost: Tickets available for purchase online. $16-$22

Christmas Ships

Now in its 69th season, the light-filled Christmas ships parade is a must-see. Dress warm, brings a thermos, and enjoy the sights!
When: Select days, December 1-17, 2023.
Where: Check out their 2022 Willamette schedule and Columbia schedule to see where the best spots are to watch.
Cost: Free!

Candy Cane Express

Enjoy cookies and cocoa and views of the Oregon coastline! Plus write a letter to Santa while you’re at it.
When: Weekends, November 24-December 17, 2023.
Where: Garibaldi, OR
Cost: Infants free, $30/child, $40/adult

Santa’s Grinchy Christmas Train at Chehalis Depot

Chehalis-Centralia Railroad & Museum hosts a short and affordable holiday train ride. Bring the kids to this fun event and meet both Santa and the Grinch.
When: Weekends, 2023 dates TBA
Where: Chehalis, WA
Cost: TBA

Mount Hood Christmas Train

Enjoy festive music and meet Santa in this charming train experience.
When: Select days, November 24-December 27, 2023
Where: Mt. Hood Railroad Depot in Hood River
Cost: In November, $54/child, $64/adult. Prices may increase in December.

Sumpter Valley Railroad Holiday Train Rides

Visit with Santa at the station, warm up with a free hot beverage, and enjoy a holiday train ride. You’ll also have an opportunity to shop at the Sumpter Christmas Bazaar.
When: December 8-9, 2023
Where: McEwen Depot in Baker City
Cost: Children 2 and under ride free, $18/child, $27/adult, $24/seniors and military, $75 family pass for two adults and two children

The Polar Express & Santa Steam Trains

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. This extremely popular event always sells out quickly.
When: November 11-December 23, 2023, select days
Where: Trains load at 1101 SW Sylvenus St., Chehalis WA
Cost: $60/person