Trains, Giant Pumpkins, And Haunted Fun – 5 Oregon Fall Adventures For Families

Sure, the forecast calls for temps in the 80s this week, but that’s what the start of Autumn has become in the NW. It’s not really fall until about mid-October now, which is odd but strangely consistent over the last several years. I remember a time back in the late 1900s when fall still started in September, but in this century it seems to start later every year. 

Fall really only gets about six real weeks, as the holidays creep up into late November around the same time the weather turns bitter cold. That means you get about a month and a half from mid-October through the end of November before people start calling it winter. By the time winter actually starts in late December, most people have had the seasonal calendar page turned in their head for weeks. Which makes sense since most people think winter is the longest season of the four. If you start in the last week of November or the first week of December and run through the third week of March, you easily get the longest season of the year. Which makes fall the shortest. Most people cling to summer weather before fall hits, then get the holiday season on the brain shortly after Halloween, which makes for an extremely short season. It’s tough not to fall into that trap, but that’s the way it is. 

So with only about six to eight weeks of fall left to go (if you can even call the weirdly warm weather right now fall, I certainly can’t), how can you get the most out of it, especially while you are treated to mostly dry weather for the time being? 

First, don’t wait until late October to start enjoying fall. It’s easy to celebrate the harvest season when the world turns its attention to Halloween and the circus of events that comes with it, but there are plenty of things to do in the weeks leading up to it. If you want a taste of Halloween a bit early, you have options for that too.

Fall Train Rides

If you like the concept of a train ride paired with seeing foliage on an autumnal Saturday, look no further. You have at least two options near Portland, and both offer unique experiences. Mount Hood Railroad in Hood River offers a special Oktoberfest-themed train ride the first weekend in October, running Friday and Saturday only. It wouldn’t be Oktoberfest without adult beverages along with Bavarian food to enjoy, and they offer those for the appropriate age groups. There are also costumes, dancing, and singing, so it’s fun for the whole family. If that sounds a little more chaotic than you would prefer, they also offer traditional fall train rides; be sure to book one on any other weekend in October, since they are only doing the Oktoberfest edition this weekend.

If you want to take a train ride this weekend and don’t want the added cost and sensory overload that could be Oktoberfest, you can stay closer to Portland and visit the Oregon Rail Heritage Museum. They are offering fall train rides for the first two weekends in October, then taking a well-deserved break until the Holiday Express starts running in late November. The Hood River train does not run on Sundays, but this one does. They’ll offer 4 train rides on Saturdays and Sundays this weekend and next weekend, then close up shop, so if you want an autumn train ride closer to town, make sure you get tickets soon. You can still venture to Hood River for a train ride through the end of October if you can’t get to the local one soon enough. The main difference between the two is the type of train. The Hood River train is a decommissioned but still modern Amtrak train, while the Oregon City train is a 1928 steam engine. So if you want your kids to hear every clickety-clack and choo-choo as the train goes down the track, probably go with the Oregon City version. But if you want a train ride and are fine with a smoother and quieter experience, the Hood River one might be the way to go. 

Hood River Harvest Festival

If you decide to go to Hood River for a train ride, you might as well go next weekend when you can also experience their Harvest Festival, which runs just one weekend a year. Kids 12 and under are free; everyone else needs a $10 ticket, which gives you admission all weekend. The festival features unique food options, live music, giant pumpkin carving, games, and inflatable activities. If you run out of things to do at the festival, downtown Hood River and the waterfront offer plenty for all ages. In good weather or not, it’s tough to have a bad day in Hood River. If you somehow run out of things to do or see, you can always jump back in the car and take the family on an adventure through the fruit loop. 

West Coast Giant Pumpkin Regatta

Giant pumpkins, a lake, a costume party, a festival, and a boat race all mixed into one. What more could you ask for? I don’t know where else you can find an event in the fall where you dress up in your favorite costume, carve a hole in a giant pumpkin, then sit in said pumpkin and use a kayak paddle to race to the finish line. On Sunday, October 18th, if you are in the Tualatin area, you can do just that. If you are competing, your friends and family can cheer you on from the shore, or if you are just there as a spectator, you can take in the scene and enjoy food and beverages from on-site vendors. The pumpkin theme doesn’t end with the races; you can also participate in pumpkin-themed bowling and golf. Live entertainers and a kids’ costume contest will also be on hand. It’s a really neat event that is just weird in the best ways. 

Scaregrounds PDX

What better way to test your mettle than to try and terrify your kids at the same place you made so many memories at the roller rink in your youth? If you’re itching for Halloween-specific outings and can’t wait until closer to the date, Oaks Park has you covered. Starting October 1st, Oaks Park transforms into a haunted theme park in the evening, Thursdays through Sundays, giving the bravest folks a chance to prove how much heart they have in a land of terrors. The first couple of weekends, the event runs from 7 p.m.-10 p.m., but for the last two weeks of the month, it’s open until 11 p.m. on Friday and Saturday evenings. If you’ve ever had the chance to experience “horror nights” at a Universal theme park, this is the closest you’ll get in Oregon. While they have haunted houses, the whole event is Halloween-themed, so you can’t just wander in and enjoy yourself while you stroll through the park outside of the haunted houses. You will encounter terrors along the way, so make sure you come prepared! 

If you have younger kids, please note that their website recommends this event is for ages 13 and up. 

Random Pumpkin Patch Adventures

Looking for fall-specific outings but not sure where you want to go? Maybe you need a little random in your life. Print out this map and put it on the wall. Draw a name from a hat and give that person a dart. Wherever the dart lands will decide the next farm you are visiting. Bonus points if you find a way to see them all!