Oregon is like an outdoor playground, where every turn of the road brings a new surprise: towering waterfalls, rainbow-colored hills, secret hot springs, volcanic lakes, and a rugged coastline dotted with lighthouses. Families looking for an adventure that’s both fun and easy will find this journey unforgettable : Here’s the ultimate loop to experience Oregon’s beauty.

Travel to Oregon with HomeExchange

Oregon Road Trip Highlights at a Glance

Day Destination Family Highlights
1–2 Portland Powell's Books, Rose Test Garden, food trucks
3 Columbia River Gorge & Mt. Hood Multnomah Falls, alpine lakes, scenic drives
4 Painted Hills & Smith Rock Colorful landscapes, easy hikes
5–6 Crater Lake & Southern Oregon Rim drive, Rogue River rafting
7 Hot Springs & Waterfalls Umpqua Hot Springs, Toketee Falls
8 Oregon Coast Samuel H. Boardman, Heceta Head Lighthouse, Cannon Beach
9 Willamette Valley Silver Falls State Park, vineyards, scenic cycling

Portland: A City That Feels Like a Garden

Start your trip in Portland, where creativity meets greenery. Wander through the Lan Su Chinese Garden, shop at Powell’s Books, or grab donuts and coffee before hitting the road. If you’re here in summer, the International Rose Test Garden is in bloom with over 10,000 roses.

Columbia River Gorge & Mount Hood: Land of Waterfalls

Just 30 minutes from Portland, the Columbia River Gorge showcases waterfalls like Multnomah Falls and sweeping viewpoints such as Rowena Crest. Families who enjoy the outdoors will love hiking or simply pausing at scenic lookouts. A short drive south brings you to Mount Hood, where alpine lakes reflect the snow-capped peak year-round.

Painted Hills & Smith Rock: Nature’s Masterpieces

Central Oregon feels almost otherworldly. At the Painted Hills, layers of gold, red, and black change with the light – perfect for sunrise or sunset photos. Nearby, Smith Rock State Park rises dramatically from the flat desert, a haven for hikers and a jaw-dropping sight for kids and adults alike.

Crater Lake: The Deepest Lake in America

Formed by a collapsed volcano, Crater Lake is the centerpiece of Southern Oregon. Its waters are the deepest, bluest you’ll ever see. Families can drive the rim road, stop at overlooks, or join a boat tour in summer.

Hot Springs & Secret Waterfalls

Southern Oregon hides magical spots like Umpqua Hot Springs, where steaming pools overlook the forest, and Toketee Falls, framed by basalt cliffs. These short hikes are perfect for families wanting a break from long drives.

Oregon Coast: Where Land Meets Legend

Head west to the Pacific and prepare for jaw-dropping views. The Samuel H. Boardman Scenic Corridor features hidden beaches, while Face Rock and Cannon Beach’s Haystack Rock bring drama to the shoreline. Don’t miss Heceta Head Lighthouse, rumored to be haunted. Kids will love tidepooling, while parents savor the coastal sunsets.

Willamette Valley: Waterfalls & Vineyards

On the way back north, stop in the Willamette Valley. Families can walk the Trail of Ten Falls in Silver Falls State Park, where you actually pass behind waterfalls. Parents may also enjoy a wine tasting, while kids can picnic among the vines.

Immerse yourself in Oregon culture with HomeExchange

Oregon is a state where each day has is lot of surprises. From volcanic peaks to misty coasts, every stop brings families closer together through shared adventures. Forget crowded attractions—this journey blends relaxation and discovery.

And to make a road trip like this even more special, imagine staying in real homes through HomeExchange instead of hotels. Swapping homes with locals means you’ll have more space, a kitchen for family meals, and insider tips about hidden gems off the tourist track. It’s a way to travel Oregon authentically, while feeling at home every step of the way.

Discover our homes in Oregon