I thought I knew Oregon. Growing up here, I was never far from the ocean or a mountain. I was always a short walk or ride to trickling streams or fast-moving rivers. But it wasn’t until I dipped my paddle into the dark waters of Hosmer Lake outside of Bend one September night that I realized my knowledge of this place merely scratched the surface. It was on a moonlit canoe tour of the high Cascade Lakes with a naturalist guide from Wanderlust Tours that an entirely different side of Oregon opened up for me.
Bats whizzed by, saving us from mosquitos and other flying insects. A heavy tail slap from a beaver warned us that their lodge was nearby. A deep, rich, earthy smell permeated the air as we quietly cut through the water. It’s an experience that has stuck with me, and — imagining myself navigating boats, life jackets and directions in the dark — one that I was happy to leave in the hands of our local expert.
As our guide skillfully led us through the dark, her knowledge of the flora, fauna and interdependencies of the plants and creatures in this ecosystem brought me closer and more connected to a place that had long been my family’s summer playground. When the tip of our canoe made the soft scratchy landing back at the launch, I felt like I was leaving a friend. The lake, our guide and others on the tour felt different to me — almost as if we had all changed just a little bit.
Maybe it’s your first time in Oregon. Maybe you were lucky enough to grow up here as well. Either way, I feel confident that experiencing the many different sides of Oregon with a local guide who lives and loves it here will change your connection to this special place.
Ready to add that experience to your plans now? Here are 14 guided (and self-guided) tours to consider.
1. Oregon River Experiences
Statewide – Whitewater rafting
Oregon River Experiences offers guided rafting trips on 10 different rivers, to suit every need and experience level. Favorite daylong and half-day trips include the forested hillside canyon of the Clackamas River just outside of Portland, the perpetually sunny Deschutes River in Central Oregon, and the crystal-clear water of the McKenzie River in the Willamette Valley. For a multi-day trip, choose between the steep and sloping canyon walls of the Owyhee River or the mighty Rogue, a river so special it was designated as Wild and Scenic to protect it forever. These trips are offered spring through fall.
2. Willamette Tides
Willamette Valley – Paddling
Bring the whole family – including well-trained dogs who are comfortable around water – to a peaceful river paddle in the Willamette Valley. Willamette Tides launches tours from the riverbank in downtown Corvallis, a vibrant city about 90 minutes south of Portland bustling with boutique shops and eateries. A 2-hour or 4-hour guided journey takes paddlers on a peaceful float down the river with a chance to see wildlife like deer, osprey, blue heron, bald eagles and more, all gear included.
3. Pendleton Underground Tours
Eastern Oregon – History, culture and heritage
Pendleton, a charming Old West town in Eastern Oregon, was home to a large population of Chinese laborers who came to work on the railroad in the late 19th century. Visitors can hear fascinating stories of these times on a guided tour through the Pendleton underground, which includes re-creations of Prohibition-era spaces like the Shamrock Card Room, an old Chinese laundry, a jail and an opium den. Tours are offered year-round and must be booked by phone in advance.
4. Hells Canyon Adventures
Eastern Oregon – Jet boating, whitewater rafting, fishing
Experiencing the wild, untamed Snake River in Oregon’s Hells Canyon – America’s deepest river gorge — is a must-do experience. Travelers can book a half-day, daylong or overnight trip with Hells Canyon Adventures through the deepest portion of the canyon, with an opportunity to see historical sites and even swim in July and August. Add another layer to the experience and try your hand at fishing for sturgeon or steelhead with a guide – if you’re lucky you could land a tasty catch. Tours are offered spring through fall.
5. Black-History Walking Tour of Eugene (Free)
Willamette Valley – History and culture
Fascinated by Oregon’s history and culture? Download Strides for Social Justice (free for Apple and Android users), a mobile app designed to accompany a self-guided walking tour of Black-history sites in Eugene. The narrated tour shares stories of local historical sites and monuments honoring the achievements of Eugene’s Black residents. As listeners walk or bike the routes through five neighborhoods, they are invited to reflect and participate in fitness activities, like circuit exercises in Westmoreland Park or leg stretches on Skinner Butte.
6. Ranger-Led Stargazing at Prineville Reservoir State Park (Free)
Central Oregon – Stargazing, camping and family activities
This state park, Oregon’s first state park to earn certification as an International Dark Sky Park, is one of fewer than 200 such places around the world. During summer 2023, the park kicks off its free ranger-led stargazing programs Friday through Sunday nights. Programs vary from lectures in the park’s amphitheater about space and nocturnal creatures to stories about the constellations. Rangers will use lasers to point out the lights of Orion’s Belt or the three stars of the Summer Triangle. Other activities might include taking a peek through “Big Doug,” a 16-inch-diameter telescope, to look at the moon’s craters or even some of Jupiter’s moons. Guest astronomers will give talks throughout the season; kids may participate in free guided art projects like painting their own constellations or building a model nest for night-loving owls. You can also catch free stargazing programs at Cottonwood Canyon State Park just north in Eastern Oregon.
7. Wine de Roads
Willamette Valley – Cycling, wine tasting
Love wine tasting, hate driving? Wine de Roads offers a unique spin on wine touring, helping travelers cycle at a leisurely pace between tasting rooms in the world-famous Willamette Valley. Groups typically stop in for a tasting at three wineries, tour the vineyards, learn about Oregon’s wine culture and soak up the idyllic views between stops. Tours are offered spring through fall.
8. Envi Adventures
Portland, Oregon Coast, Central Oregon, Mt. Hood and Columbia River Gorge – Aerial tours, charters
Take in the vast beauty of Oregon from above with an aerial tour or charter flight with Envi Adventures. The expertly guided tours offer a rare chance to glimpse these iconic sights from above – from a romantic sunset flight above Portland to an hourlong tour of Mt. Hood and Mount St. Helens, a 2-hour trip to the Oregon Coast or a day trip to Sunriver for a sun-soaked day in the high desert. The most popular tour is Wonderful Waterfalls, which showcases the Columbia River Gorge and its jaw-dropping cascades. Tours are wheelchair accessible and offered year-round.
9. Adventures Without Limits
Statewide – Kayaking, canoeing, whitewater rafting, paddleboarding, hiking, wildlife touring, camping, rock climbing, snowshoeing, cross-country skiing
This nonprofit outfitter aims to support outdoor recreation in Oregon regardless of ability or access. Groups or individuals can sign up for a guided adventure with no equipment or experience required. Visitors seeking adaptive options can choose from a sunset paddle tour or a multi-day rafting trip, a rock-climbing excursion at local crags or backpacking or snowshoeing in the wilderness for a multi-sensory experience.
10. Ossies Surf Shop
Oregon Coast – Surfing, kayaking
For regulars or absolute beginners, this full-service surf shop specializes in year-round surf lessons and kayak tours around Newport, on Oregon’s Central Coast. Surf lessons (including women’s-only lessons) take place in beginner-friendly spots, and kayak tours are peaceful floats along Beaver Creek, including special tours for sunrise and sunset. Both tours include all equipment and instruction. Ossies’ ethos include promoting Leave No Trace principles, and a portion of their proceeds go to support activities for at-risk youth and local trail maintenance.
11. Kayak Tillamook
Oregon Coast – Kayaking, canoeing, photography, birding
The pros at Kayak Tillamook match guests’ level of fitness and experience with their paddling tours for the perfect guided experience on the water. Launches happen at several different areas along Oregon’s North Coast and take paddlers through crystal-clear estuaries, secluded old-growth Sitka spruce forests and along wildlife-filled salt marshes. Moonlight and moonrise sunset tours are available, and the most popular excursion is a tour of Netarts Bay – home to some of the Coast’s tastiest clams and oysters. Paddle on your own or share a tandem.
12. Word is Bond Black History Walking Tours (Free)
In the Portland area, community members are invited to take part in the free, guided “In My Shoes” walking tour (check website for next event dates). The event features nine walking tours in neighborhoods across Portland, led by the community ambassadors of Word is Bond, a nonprofit that serves Black men ages 16-21 with leadership and internship programs. The tours are designed to highlight the voices, dreams and experiences of rising Black men as well as the neighborhoods in which they live. Ambassadors highlight important places in their community, share personal experiences and read original works of poetry. Neighborhoods include Lents, Mt. Scott, Cully, Kenton, Parkrose, North Portland, Southwest Portland and Beaverton.
13. Throw Snakes Tours
Portland – Nightlife, culinary, culture
Sometimes travelers are looking to hang out with locals, hear cool stories and experience off-the-beaten-path sites that aren’t in most guidebooks. Owned and operated by a fun-loving local, Throw Snakes Tours specializes in just that, with two unique guided tours in Portland that cater to guests ages 21 and older. A day tour explores local oddities; an evening tour explores unusual bars in town. Both are designed for travelers looking to “throw snakes,” or do something memorable or unexpected.
14. Oregon Food Trails (Free)
Statewide – Culinary, agritourism
Eating your way through a new place is a great way to travel — and Oregon has plenty of bounties to enjoy. Oregon Food Trails showcase the freshest local offerings of farmers, fishers, brewers and chefs. Each trail features the signature flavors of the region, from wine and beer to fresh fruit and produce and more. Before you go, make sure to confirm business hours since many vary by season. Support local businesses and make sure to bring back treats for yourself and friends to enjoy.