Let’s face it: having an impressive mountain as the background to your vacation (and in subsequent photos) is never a bad idea. At 11,250 feet above sea level, Mt. Hood is Oregon’s tallest mountain. Surrounding this magnificent peak is Mt. Hood Territory, a tightknit group of 14 communities with tons of local offerings to explore.   

Summertime brings wildflowers blooming, u-pick farms bursting with fresh produce and amazing views for maxing out your camera roll. Covering 1,870 square miles (bigger than the state of Rhode Island), Mt. Hood Territory’s outdoor adventure options encompass everything from farm loops and hiking trails to kayaking and mountain biking. 

It can be daunting to know where to start, so here’s our 3-day guide to road-tripping around this area to see the best of it. Plus, you can even play road trip bingo on your phone as you go along. 

Day 1 

About 6 miles southeast of Portland, Milwaukie is a riverfront community full of independent shops and restaurants, plus dogwood trees that flower in spring. Grab some breakfast sandwiches (and some snacks for the road) at Good Measure, a café/grocery store which uses locally sourced, seasonal ingredients, or sit and eat Thai specials like pineapple curry, pra ram or cashew nut noodle at Giving Café & Bistro. For more options in one spot, head to 1847 Food Park, where up to 17 food carts are ready to serve. Before leaving Milwaukie, stop at The Milwaukie Beer Store’s craft bottle shop or pick up a six pack at pFriem Family Brewers for you and your designated driver to enjoy later that evening. 

Properly fueled, get back in the car and head east for about 15 miles via OR-224 and OR-212. The town might be called Boring, but that’s hardly the case at the North American Bigfoot Center. Here, you’ll meet “Murphy,” a life-sized Sasquatch replica in the center of the exhibit hall that just begs to be photographed. Get your fill of Bigfoot evidence and historical artifacts, then head to the gift shop for unique souvenirs like footprint casts. Kids aged five and under are admitted for free.

Take Highway 26 east 23 miles to Welches, one of the Villages of Mount Hood. For the traditional hotel experience, drop your stuff off at Mt. Hood Oregon Resort, a 147-room hotel at the base of the mountain. For a quirkier stay, choose Mt. Hood Tiny House Village, where seven unique tiny homes give new meaning to the phrase "full of character." (Click on their website to read the ‘bio’ of each home.) 

If you’ve got time before dinner, check out the Wildwood Recreation Site for a bit. Located along a bend of the Salmon River and surrounded by the Mount Hood National Forest, this 550-acre land is bursting with old-growth Douglas fir, western hemlock and western red cedar trees. You can look for wildlife (like birds, beavers and muskrats) on the 3/4-mile-long Wetlands Trail. There's also an underwater viewing window for spotting salmon and steelhead trout. 

After you’ve finished exploring, head into town in Welches, where dinner choices include Chicali Cantina for fresh Mexican food and seasonal cuisine at The Rendezvous Grill, a local favorite for three decades.  

Day 2 

Wake up early and head to family-owned and operated Mt. Hood Roasters Coffee Company in Rhododendron, only four miles east along US-26. They air-roast small batches of beans to bring out the full range of natural flavors and also sell pastries and breakfast sandwiches. 

Continue east on US-26 to Government Camp, where you can team up with Mt. Hood Outfitters for a guided tour of the mountain's rugged terrain. Summer tours include hiking and whitewater rafting. On these excursions, knowledgeable guides can teach you about the area’s history, culture, wildlife and plant life. Alternatively, you can head to Timberline Bike Park at Timberline Lodge for some serious downhill mountain biking; there is a mix of beginner and advanced trails, as well as bike rentals and lessons. Another summer-only activity in this area is Mt. Hood Adventure Park at Skibowl; set in Mt. Hood National Forest, here you can experience a half-mile dual alpine slide, scenic sky chair ride, freefall bungee jumping, ziplines, go-karts and bungee trampolines.   

For lunch, stick around in Government Camp to dine at one of its many alpine options serving burgers, pizza and sandwiches, like The Ratskeller or Glacier Public House. Don’t miss out on sampling beer from Mt. Hood Brewing Company while you’re here as they literally brew ale with glacial water from Mt. Hood. 

Once your belly is full, head west on US-26 for about 40 miles to Estacada, located along the Clackamas River. Stroll around the town to see the mural art and visit shops like Wade Creek Vintage Marketplace, where more than 25 vendors offer vintage and local goods, and Mossy Rock Gifts/Nature Shop, where you can pick up crystals, natural history books and locally made jewelry. Stop by Granny’s Drive-Thru (on foot) for a milkshake.

From Estacada, you have a few options for the afternoon. Go Class III-IV whitewater rafting on the Clackamas River, if you didn’t go in the morning. Head to Milo McIver State Park for hiking or kayaking (rentals are available); there’s even a world-class, 27-hole disc golf course if you want to try your hand at that. Soothe your muscles for hours at Bagby Hot Springs, accessible via OR-224 E (skip the local roads and check weather conditions for safety). You can even rent a pontoon boat at Promontory Park Marina to explore the 350-acre reservoir on your way to or from the springs.  

Stay overnight at Camp Colton, about 13 miles south of Estacada, where you can choose from a yurt (with a wooden stove), cabin or campsite. Nearby dinner choices include historic Colton Café, known for its hand-dipped fish and chips as well as its chicken-fried steak, or Fir Valley Pour House, which has a seasonal menu that uses fresh, local ingredients.    

Day 3

Make the most of your travel day by heading around 8 miles west on OR-211 to Molalla to Alpacas at Marquam Hill Ranch. Home to more than 55 alpacas, this working ranch is not a petting zoo, but more of an educational, hands-on tour to learn more about the livestock. (Appointments are required in advance.) At nearby Out in the Garden Nursery, you can bring a picnic, stroll the garden grounds and meet friendly animals (think goats, dogs, chickens and cats). 

On your way back north to the airport via OR-213, make time to visit historic Willamette Falls, the second-largest waterfall by volume in the United States and known as the “Niagara of the Northwest”. If the weather is nice, you can kayak to the falls near Oregon City (and also see the historic Oregon Trail). You can also get a bird’s-eye view of the falls at the Museum of the Oregon Territory, which overlooks the water.

Just 6 miles north of Oregon City is Lake Oswego, a culinary destination where you can grab a bite downtown while enjoying the views. Sourcing its meat, seafood and vegetables from local vendors and farmers, Mann’s on the Lake is a New American style restaurant with a patio for outdoor dining. As the name implies, Lake View Taphouse overlooks the water, offering everything from white cheddar and Swiss fondue share boards to seafood entrees. If you have time, you can stroll downtown to pick up any last-minute souvenirs before boarding your flight and planning your next trip back.    

Ready to go? Start planning your road trip to Mt. Hood Territory now.