If you’re looking for some quirky, educational, and rejuvenating adventures close to Portland this summer, our family of five with kids ages 5, 7, and 9 tested out two home bases that check all these boxes. Pack your hiking clothes, swimsuits, and curiosity for an Oregon road trip loaded with family-friendly escapades.
Day 1 Home Base: Hilton Garden Inn Clackamas Portland
The newly renovated Hilton Garden Inn in Clackamas is just 20 minutes from Portland and lands you central to walkable amenities like Target, Starbucks, restaurants, and a large shopping mall—Clackamas Town Center, home to over 200 stores, many restaurants, a 20-screen movie theatre, and Dave and Busters.
Also key for families: Seasonal outdoor pool (open Memorial Day to Labor Day), coin laundry, on-site restaurant with in-room dining available, spacious updated rooms with coffee makers and mini-fridges.
How We Spent a Day Near Clackamas
Just 7 minutes down the road, we hit up The Brew, a family-friendly coffee shop in the heart of Gladstone. This charming café has a small-town feel, family-roasted beans, and good breakfast sandwiches. Bonus: the café welcomes kids with stashes of toys and games inside and on their outdoor patio. We gladly took the invitation to play a game of Monopoly Deal while our breakfast sandwiches were being made.
Right next door, Cookie Pot Children’s Resale Boutique caught our eyes, so we stopped to peruse. My kids convinced me to buy them all “adventure bracelets” made by a local boy about their age (go, young entrepreneur!). The bracelets are loaded with a compass, whistle, and components that can make sparks for fire starting (you’ve been warned!). My kids also filled a bag of high-quality clothing in some of our favorite brands for under $100. I highly recommend browsing here—you never know what you’ll find!
End of the Oregon Trail Visitor & Interpretive Information Center, Oregon City
After the quaint Gladstone stops, we drove just 6 minutes across the river to the End of the Oregon Trail Visitor & Interpretive Information Center in Oregon City—a museum so engaging that it’ll trick your kids into learning history! We took over an hour to go through the interactive exhibits and an additional 30 minutes to watch the Bound for Oregon documentary. This stop was unexpectedly one of my kids’ most memorable stops of our road trip.
My kids were engrossed in their Oregon Trail role-playing, which gave us parents a chance to actually read all the signs we wanted to. If you have boys or young kids, you’ll resonate with my 7-year-old son’s review of this museum: “It’s cool because it has real poop—big and small bison chips that you can touch!” (Don’t worry, we were told the dried poop is sanitized for safe handling.)
The dreaded souvenir shop? Not here! The souvenir situation at the End of the Oregon Trail Museum is a win-win. Included with paid entry, everyone gets to dip their own candles and make their own rag dolls—my son got creative and made a “drone.”
My five-year-old daughter didn’t want to leave the schoolhouse where you can dress up as pioneers, sit in a replica classroom, and use real chalk. My active boys spent their energy lugging and packing sacks of supplies into their model wagon. A scavenger hunt with a sweet prize (honey stick) also motivated them to thoroughly check out each exhibit. All in all, my kids rated this museum 10/10 for the poop, candle making, and playing school.
Eats and Oregon City Stops
For lunch, we stopped at The Hive Social in historic Oregon City. This vibey spot supports local farmers and ranchers with their farm-to-table menu. From a veggie-forward bowl with herby tahini to a not-so-boring “Boring Burger” with chutney, aioli, house pickles, and caramelized onion, to benedicts, to hearty biscuits and gravy, everyone will find something to savor.
Even the kids’ menu has farm-to-table ingredients like a locally sourced beef patty in their cheeseburger. If your kids are more sophisticated in their tastes, they might like the kids’ avocado toast or Caesar salad with pecorino and capers.
Don’t miss the aebleskivers (AKA Danish pancakes) served with lemon curd, seasonal preserves, and vanilla whipped cream. My kids devoured these almost before my camera could eat them first. We also treated our kids to their homemade sodas while I sipped on a Lavender Lemon Mimosa.
After a satisfying brunch, we explored Oregon City on foot, walking just a few blocks to the iconic Oregon City Elevator. I explained to my kids that this elevator is the only outdoor municipal elevator of its kind in the United States, which is just a fancy way of saying it’s a vertical street elevator that drops you from one street, down to another without stairs. Because kids are literal, I then had to explain that this elevator was not going to drop us like the Tower of Terror.
The elevator’s panoramic views highlighted different landmarks and gave us a bird’s-eye view of the city. At the bottom, we stumbled upon a family-owned hobby, antique, and collectibles store, Coin Corner and Hobbies, which was established in 1962. My boys flipped through some Pokémon cards, and we walked out with a 90’s Polly Pocket for my daughter.
Before driving off to our hike, we stopped to swing at a park near where we parked, because why not? The Oregon City Library has an old-school tall metal slide and a row of four high swings that are on top of soft rubber surfacing. All three kids competed for how high they could swing. The attached spray park is open in the summer months and would be perfect for cooling off on hot days.
Easy Hikes in Happy Valley
Back in the car, we made a quick pit stop at the Oregon City 7-11 to load up on some cold drinks to motivate our walkers on a hot day. Hidden Falls Nature Park in Happy Valley, an unexpected nature trail in the middle of a suburb, is a hidden gem.
As you walk the zig-zagging 1.2-mile paved path, you’ll trade rooflines for treetops within minutes. Don’t let this short mileage fool you—this path is steep and there was some complaining on behalf of my children. In fact, one of them said it was “the worst day of their life”. Who can relate to this hiking drama? Truthfully, it was nothing that a little bribery couldn’t remedy. The stunning timber bridge over Rock Creek and the falls just beyond it were worth the whining.
By the end of this very full but fun day, we all needed some downtime (and A/C!), so we drove back to Clackamas Town Center to catch an early movie. Because we were in full vacay-mode, we decided popcorn was dinner and topped it off with some Jamba Juice smoothie bowls at the food court before calling it a night.
Day 2: Adventuring From Clackamas to Our New Home Base at Mt. Hood Oregon Resort
After a quick breakfast and caffeine fix, we packed up and made our way to Boring, OR, where the not-so-boring North American Bigfoot Center is located. Our kids were anticipating this stop for our entire trip.
North American Bigfoot Center
Going into this trip, 2 of the 5 of us believed Bigfoot was real. After a thorough investigation at the North American Bigfoot Center 3 of the 5 of us walked out as big fans, and the rest of us held our skepticism more loosely.
Upon entering, you’ll find convincing evidence of Bigfoot encounters, a small theatre that plays documentaries and films, and displays of artifacts and evidence. We spent about an hour here exploring the kid-friendly exhibits. A word of warning: Bigfoot became a little too real, and at bedtime, I had to help reassure them that Bigfoot was not coming into our room that night. My kids woke up the next day with less fear and on a quest to find signs of Bigfoot in the Mt. Hood Territory.
Sandy Eats
Following the quirky yet convincing Bigfoot museum, we drove to Sandy for lunch and treats. Anyone going through Sandy should stop at the renowned donut shop, Joe’s Donuts, where they still make their donuts the same way they did when they opened back in 1974. It’s a popular stop for locals and tourists alike, and they do sell out—when we arrived around 1 p.m., half of the pastry case was empty, but we still got to try one of their most popular fritters and maple bars. You can’t go wrong here.
After we secured our treats, we stopped for lunch at AntFarm Café & Bakery, where you can feel good about eating fresh, locally sourced food and supporting the community. Ant Farm Café is a part of AntFarm Youth & Family Services, so your purchase supports their work with youth, families, and the community.
Not only is this spot warm and welcoming, but my daughter found some coloring sheets and toys to play with while we waited for our food. We enjoyed the Reuben sandwich, homemade granola and yogurt, breakfast burrito, and “Old Fashioned Plate” breakfasts.
Following brunch, we drove just under 20 minutes to Highland Farms. Driving through the forested gravel road to its entrance was like stumbling upon a haven in the woods. Once there, Highland Farms greets you with a giant intricately carved wooden sign, beautifully landscaped grounds, and of course, the pastures where the beloved Highland cows await your visit.
Highland Farms
Book your hour-long private tour, don your closed-toe shoes, and be ready for your heart to melt as you get up close with these gentle giants. My kids adored brushing and petting the mama cows and their calves. Fun fact: their horns are warm to the touch because of the blood vessels in them.
While it was hard to leave the charming and oh so photogenic cows, we had to spread the love to the other animals, like the White Peacocks, which we had never seen before. Fanning their feathers, they are a captivating sight to see! Highland Farms is home to several White Peacocks, Icelandic Sheep with their guard dogs (Great Pyrenees Anatolian Shepards), Guineafowl, and chickens.
While we didn’t stay overnight, my kids wanted to! The farm has three options for overnight guests to choose your own adventure. The Bonnie Lass Cottage with prime highland cow views is beautifully curated for a comfortable and relaxing retreat with a private cedar hot tub, BBQ, and ability to open the garage door for a breezy living room space. The Camp offers a cozy Airstream and a Glamping Tent. Both are tucked on the edge of the wooded trails with horseshoe and fire pits. Lastly, “The Whole Farm” books you the 7-bedroom house that can accommodate up to 16 guests. The house overlooks the Scottish Highland Cows, gives you full farm access, and two cedar hot tubs.
Highland Farms Nordic Spa
When our farm tour ended, I sent my kids with my husband to our next hotel stay at Mt. Hood Oregon Resort. I got to soak up a bit more of the serene forest setting at the Highland Farms Nordic Spa. All you need to bring is a swimsuit and sandals.
For 90 minutes, you can cycle through a wood-burning sauna, soothing steam room, and outdoor cold plunge at your own pace. Take a break to relax on the deck surrounded by old-growth forest or indoor lounge area. Everything about this experience was peaceful, rejuvenating and gave me the best night of sleep!
Mt. Hood Oregon Resort
Just 10 minutes away from Highland Farms, the Mt. Hood Oregon Resort was our next home base. While a prime location for many of the region’s popular destinations, there’s plenty to do if you want to ditch your car, stay on property, and have a slower-paced vacation.
The hotel’s rooms are remodeled with lots of space for kids to spread out. Our room had a wood-burning fireplace and robes for the entire family, for ultimate cozy vibes. All rooms have a Keurig coffee maker, mini refrigerator and freezer, and microwave. And while we stuck to swimming and hiking, the resort also offers a playground, basketball, tennis, sand volleyball, horseshoes, croquet, and lawn bowling.
What kids don’t love a hotel pool? At 85 degrees and open year-round, your kids can swim till they need to get out because their lips certainly won’t turn blue in this pool! My kids worked up an appetite and we headed to the nearby Koya Kitchen for dinner, an Asian food truck restaurant, with an expansive menu featuring homemade curries, noodles, sushi, and other Japanese and Indian dishes. We ordered a variety of things from the menu—all of it was fresh and delicious. My kids recommend that each person order their own Musubis.
If you’ve never had one of these popular Hawaiian snacks, Koya Kitchen makes these grilled Spam delicacies to order. Spam is layered on a block of sticky rice, wrapped in seaweed, and drizzled in a sweet and salty sauce. We all would rate Koya Kitchen 10/10 for food, ambiance and per the kids, “you get to eat in a real school bus!” The meal is a memorable experience we’d all like to repeat.
After dinner, we ended our evening playing games in the hotel lobby—a lobby you’ll actually want to spend time in for the cozy atmosphere, kids’ coloring table, and lots of tables to spread out on and connect over playing games.
Day 3: Play at Mt. Hood Oregon Resort and Hiking
Our kids grabbed a few items from Mt. Hood Oregon Resort’s free continental breakfast before getting some wiggles out at the playground and putting on the designated golf green. We didn’t travel with clubs but we were able to borrow a few putters and bought some golf balls. If you’re golfers, you won’t want to miss this picturesque and affordable golf course. Bring your own gear or pack light and rent theirs.
After check-out, we stopped at Coffeehouse 26 for espresso drinks and hot breakfast sandwiches. With an extensive syrup menu, I chose an iced lavender latte. My kids flipped through some of the used books for sale while waiting for our order.
Wildwood Recreation Site
Before venturing home, we took advantage of another hike in Mt. Hood Territory’s over 1,000 miles of trails. We bought a $5 daily pass (by credit card machine) and hit the trails at the Wildwood Recreation Site.
Though you could spend all day here, we had time to trek the Cascade Streamwatch Trail (3/4 loop) and the Wetlands Trail (3/4 mile loop). Both are suitable for all-terrain strollers. My kids will never admit to liking “hikes” but being in nature where they can discover creatures is their happy place.
The Cascade Streamwatch Trail is dotted with informational signs with flaps you can flip to uncover facts, spots to get down to the Salmon River, and a unique opportunity to go under the stream by looking through the underwater fish viewing chamber. My kids enthusiastically spotted crayfish, sculpin, chinook salmon and cutthroat trout fries.
Moving into a different ecosystem, the Wetlands Trails takes you through multiple stations along the boardwalk with a kid-friendly guide book at each one. Cattail Marsh, Beaver Dam, Ghost Forest, Skunk Cabbage Corner, and the Wetland Stream each provide different windows into this mountain marsh.
If you walk quietly under the trees dripping in moss, you’ll hear trickling streams, tree branches rustling overhead, and the music of birdsong. We spotted salamanders, a baby bat, and many salmon fry on our short visit. If you have more time, pack a picnic, some sand toys, swimsuits, and stay a while.
We crammed it in on our 3-night Mt. Hood Territory stay and barely touched all that this region has to offer. It is jam-packed with family-friendly destinations that are easy on the wallet and sure to make lasting memories. I already have a list of places I want to visit (and re-visit) next time! Copy our itinerary or adapt it to make it your own with endless ideas on mthoodterritory.com.
*Note: The author was given complimentary accommodations at the Hilton Garden Inn Clackamas Portland and Mt. Hood Oregon Resort, but the opinions expressed in this article are her own.
