The holidays are the highlight of many children’s year, and combining them with festive train rides and enchanting boat trips will have your kids over the moon! In this guide, we’ve compiled some of the best holiday train and ship experiences in the area. Many of these magical journeys feature a special appearance by Santa Claus, and most include the warmth of delicious hot chocolate. Get ready to create unforgettable memories this holiday season—let the festivities begin!
MAKE MAGIC AND MEMORIES AT BRIDGEPORT VILLAGE. This post is generously sponsored by Bridgeport Village. Don’t miss their holiday happenings, including visits with Santa, Mrs. Claus story times, musical performances, a whimsical holiday parade, and more! Discover the magic of the holidays with an exclusive family-friendly event calendar at Oregon’s premier shopping destination — the most festive place for holiday ambiance, gift giving, and everything else on your list.
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: Select dates, November 30-December 27
Where: Portland Spirit
Cost: $60/child, $80/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 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. This ride always sells out, so don’t wait!
When: Weekends, November 29-January 4
Where: All trains load at the Oregon Rail Heritage Center, 2250 SE Water Ave., Portland OR
Cost: $25/child, $34/adult, $105/family of four. Children ages 2 and under are free on lap. 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 enter an ugly sweater contest and enjoy hot beverages! Please note, no trees for purchase this year.
When: Weekends, November 30 through December 22
Where: Train loads at 207 N. Railroad Ave., Yacolt ,WA
Cost: Tickets available for purchase online. $16-$22
Christmas Ships
Now in its 70th season, the light-filled Christmas ships parade is a must-see. Dress warm, brings a thermos, and enjoy the sights!
When: Select days, December 5-22
Where: Choose a spot along one of the routes.
Cost: Free!
Candy Cane Express
Enjoy cookies and cocoa and views of the Oregon coastline! Plus write a letter while you wait for a visit from Santa.
When: Weekends and select weekdays, November 29-December 23
Where: Garibaldi, OR
Cost: For indoor cars, infants are free, $33/child, $44/adult. For covered outdoor cars, infants are free, $27/child, $35/adult.
The Polar Express Train Ride at Mount Hood Railroad
Enjoy festive music and meet Santa in this charming train experience. Everyone receives a cookie and hot cocoa, and you may also bring your own snacks and drinks.
When: Weekends and select weekdays, November 22-January 4
Where: Mt. Hood Railroad Depot in Hood River
Cost: $49-$109
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 9-December 22, weekends and select weekdays
Where: Trains load at 1101 SW Sylvenus St., Chehalis WA
Cost: $64/person
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