If you grew up guiding your wagon across The Oregon Trail, you already know the Beaver State is the stuff of legends. While you may not have to ford a river or hunt for pixelated buffalo, an easy getaway to Oregon’s Mt. Hood Territory will still give your family plenty of stories to tell.
So gas up the car, pick up some snacks, pack your favorite hiking boots, and bring the kids along for a real-life journey, no dysentery required. Oregon’s Mt. Hood Territory is the perfect fall escape, filled with pumpkin patches, scenic hikes, crisp mountain air, and cozy small towns that make you feel like you’ve stepped into a storybook.
Whether you’re chasing autumn leaves, sipping cider, or exploring farms and festivals, your family will discover that the trail to adventure is alive and well in Oregon’s Mt. Hood Territory.
Adventures by Day, Cozy Stays by Night
Why choose between thrills and downtime when you can have both? We’ve rounded up our favorite places to run wild and celebrate the season, as well as our go-to spots to unwind together as a family. It’s the perfect mix of adventure and comfort, giving parents peace of mind and kids a season full of memories.
5 Fall Gems to Discover as a Family in Oregon’s Mt. Hood Territory
With all there is to see, do, and eat, it’s hard to just pick five, but these really are the apple of our eye this season.
1. The Mt. Hood Territory Harvest Trail tops our list, and while it’s just one gem, it’s a multifaceted pick, full of farms, pumpkin patches, corn mazes, and of course, animals. Frog Pond Farm Pumpkin Patch, with their free-roaming llamas, is a perennial favorite for something you don’t see anywhere else. For older kiddos up for a challenge, check out the new corn maze at Yesteryear Farms, complete with 4 miles of trails. And all the gamers will happily drop their devices for the Minecraft-themed fall festival at Liepold Farms. In case of rain, stay dry in the barn at Kirchem Farm with loads of activities (and 35 types of pumpkins and gourds!).
Don’t forget to complete five Harvest Trail passport activities and earn a custom trucker hat. What’s more, for every passport redeemed, a Thanksgiving meal will be provided to a local family in need through the Sandy Community Action Center.
Looking for more farms? 6 Family-Friendly Farms to Visit has even more ideas.
2. If hiking is the name of your game, then run, don’t walk, to the newly reopened Trillium Lake Loop. This kid-friendly trail offers 2 miles of scenic flat terrain (great for strollers!) with scenic views of Mt. Hood as you make your way around Trillium Lake. The trail crosses wetlands that provide bird-watching opportunities. Plenty of benches make for easy snack and water breaks.
3. Looking for a little culture? Make your way over to Lake Oswego, where nature meets sculpture on the Gallery Without Walls art walk. Many of the sculptures interact with the environment, like moving in the wind or changing colors and moving with the sunlight. Plus, unlike traditional museums, little hands are encouraged to touch the artwork.
4. Do you believe in Bigfoot? Whether you do, don’t, or are unsure, the North American Bigfoot Center will help you make up your mind. Dozens of displays feature a wide array of Bigfoot evidence and historical artifacts, with a life-sized Sasquatch replica named “Murphy” acting as a centerpiece and a popular backdrop for family photos. Be sure to post them in your Tinybeans journal!
5. You may not have made it all the way west during elementary school, but as a grown-up, you can take your kids to the end of the Oregon Trail IRL. The End of the Oregon Trail Interpretive Center offers interactive films and exhibits that include authentic Oregon Trail era activities and games. Visitors can pack their own wagon, dress up, make butter, and dip their own candles!
5 Places to Stay After a Day of Play
After a day spent apple-picking, hiking past golden leaves, or chasing waterfalls near Mt. Hood, you’ll want a cozy, dependable place to land that feels like home. Oregon’s Mt. Hood Territory has tons of family-friendly options ready to be your home away from home this weekend.
1. If you’re looking to get a little bougie, the brand new AC Hotel Portland Lake Oswego is ready to welcome guests. The mix of European-style touches (sleek design, minimal clutter) plus practical services for families gives it a feel that’s upscale but not stuffy. Bank on a dependable, rejuvenating stay, with blissful mornings free from whining and stress-free evenings. You’ll be close to urban conveniences (shops, restaurants, services) but can easily escape into nature.
2. The Hilton Garden Inn Wilsonville is another great home base for orchard visits, small towns, forest hiking, and leaf-peeping. Once you check in, there’s no need to venture back out for dinner. Taste the seasons and Indulge in a glass of wine, locally crafted beer or cuisine inspired by Pacific Northwest traditions at the newly opened Parkway Grille. Tuck the kids in early and cozy up by the outdoor firepit before another action-packed day.
3. Want the beach without the mess? The saltwater pool at Residence Inn by Marriott Portland Clackamas is calling your name. Your kiddos will love not having their eyes burn from the chlorine—and adults be all about the fact that there’s not a grain of sand in sight. After swimming, don’t worry about everyone getting showered and dressed, because you can order in or prepare dinner in your room’s fully equipped kitchenette.
4. Newly renovated and a great value, the Best Western Lake Oswego is another convenient location offering access to both Portland and all the best farms, parks, and hiking trails. It’s also convenient for larger families with interconnecting rooms and suites so everyone can have the space and comfort they need. Have a four-legged explorer in your pack? No problem, well-behaved pets are welcome.
BONUS: All of these hotels have indoor pools! So your kiddos will burn off even more energy and fall asleep like it’s their job. And did we mention the free breakfast?
5. Sometimes the best family adventures start with a front porch and a set of house keys. From rustic cabins tucked in the forest to cozy chalets with fireplaces and hot tubs, renting a house in Oregon’s Mt. Hood Territory can make it easy to live like a local while keeping family routines intact (and not having to worry about your kids screaming down the hotel hallways). With an office conveniently located on Mt. Hood All Seasons Vacation Rentals can not only match you to the perfect retreat, but also has staff ready to help visitors with any phase of their stay. Prefer to book yourself? Check out Vacasa.
Don’t let the autumn leaves fall without you there. Whether you’re craving crisp hikes through golden forests, cuddly nights by the fire, pumpkin farms and cider tastings, or simply the joy of hearing your kids yell, “Look, a waterfall!”, Oregon’s Mt. Hood Territory has it all. Rooms and cabins are filling fast as the season shifts to russet and gold. So go ahead: pick your cozy stay, pack your suitcase, and press “Book.” Your next family story starts right here, under alpine skies, among orchards, and within moments of mountain trails waiting just for you.
TLDR: No matter what you choose to do or where you choose to stay, you can’t go wrong with a fall weekend getaway in Oregon’s Mt. Hood Territory.
