Start working your way south, but take a detour to Silver Falls State Park. Stretch your legs on the Trail of Ten Falls, a seven-mile loop that packs in (you guessed it) 10 waterfalls, including the 177-foot-tall Silver Falls. If you plan on making more of this beloved state park than a day hike, take in the view from atop an old-growth tree, or even spend the night up there. Tree Climbing at Silver Falls provides the gear and expertise for tree climbing, ensuring a safe and fun outing. 

Post-hike, grab a bite at the Little Leaf Cafe or the Noble Fox in the historic town of Silverton. Logging put the town on the map, though now it’s known more for its historic architecture, restaurants, and boutique shops. 

Silverton makes for a good stopping point, but if you’d like to put in some more miles, Albany and Corvallis make for good mid-valley stops as well. If you decide to push on, rest up and refuel with the Mid-Willamette Valley Food Trail as your guide to the best culinary experiences in the area. 

Travel tip: If you have time for a stop between Newberg and Silver Falls State Park, make a stop at the Flying Bee Ranch in Salem. Load up on local bee products, or even book an experience to meet the bees themselves. 

Overnight: Spend the evening at a cabin in Smith Creek Village at Silver Falls State Park or The Oregon Garden in Silverton. There are also a number of hotels and bed and breakfasts in Albany or Corvallis.

Continuing south, head towards Eugene and Cottage Grove. For some of the best views in the area, take a hike to the top of Spencer Butte, just outside of Eugene. Short and sweet, this moderate (and occasionally strenuous) 1.7-mile loop leads hikers through lush forests before topping out at the highest point in the surrounding valley. 

As you’d expect from a college town (go Ducks!), beer reigns supreme in Eugene, though breweries like Ninkasi and Hop Valley have refined the process into an art. Start there, but don’t overlook the smaller breweries. For a comprehensive guide, look no further than the Eugene Ale Trail. Brewery hopping is also a great way to explore Eugene’s funky neighborhoods and downtown, including a tour on the Mural Trail or a visit to the Museum of Natural & Cultural History. Pro tip: cover more ground by renting a bike share ride from PeaceHealth Rides.

Further south, Cottage Grove offers another excellent opportunity to trade four wheels in for two. One of the more unique features of this region is the abundance of covered bridges. These historic wooden structures were built to withstand the infamously wet winters of the Pacific Northwest, and many still stand today. The 36-mile Covered Bridge Scenic Bikeway begins in historic downtown Cottage Grove and loops around Dorena Lake. This includes sections of shared roadways, but part of it can be done as an out-and-back trip along the Row River Trail, a bike/pedestrian-only path along the north side of the lake. Back in town, treat yourself to a hearty meal at the Axe and Fiddle Public House or a burger and ice cream at the throwback Bonanza Drive-Up.

Travel tip: If you’d rather take a scenic drive than go for a bike ride, take a cruise along the McKenzie River Scenic Byway instead. 

Overnight: There are plenty of hotels in Cottage Grove, or check out a local bed & breakfast, such as the Sweet Springs Family Farm just south of town. 

From Cottage Grove you’ll leave the Willamette Valley and enter the Umpqua Valley wine region, home to over 37 unique wineries. You’ll be in close proximity to the charming, historic towns of Oakland and Sutherland, and also at the beginning of the Great Umpqua Food Trail. 

Here is where you’re also entering southern Oregon, and there’s no better way to get acquainted with it than to pay your respects to its raging rivers. You’ve probably heard the term “Wild and Scenic,” but here’s your chance to really learn its meaning. More than just a description, the term refers to the Wild and Scenic Rivers Act of 1968, a law that protects certain rivers that have significant natural, cultural, or recreational value. Three such rivers are found in southern Oregon–the Rogue, North Umpqua, and Upper Klamath. 

Take a drive from Roseburg along the Rogue-Umpqua Scenic Byway (Highway 138), also known as the Highway of Waterfalls. This 172-mile stretch of highway winds along the Wild and Scenic Rogue and Umpqua rivers, passing by more than a dozen waterfalls. Opportunities for rafting and hiking abound on this stretch–whether it’s a river trip expertly navigated by the guides from Orange Torpedo Trips or a waterfall tour led by Umpqua’s Last Resort. 

Allow yourself to spend as little or as much time on this route as you wish, but we’d recommend at least making a stop at the 294-foot-tall Watson Falls–the third tallest in the state–or the Gorge of the scenic Rogue River as it cascades down from Crater Lake to the Pacific Ocean. 

Tip back a glass at Meadow Estate Vineyard & Winery for sweeping vineyard views, or visit Reustle-Prayer Rock Vineyard to sample award-winning wines, including their famous Grüner Veltliner. For more spectacular sights, Cooper Ridge Vineyard serves handcrafted wines perched above the Umpqua River. If you’re craving an alternative to wine, Backside Brewing has locations in both Sutherlin and Roseburg. For an entirely different agricultural experience, visit River Ranch Oregon Olive Oil, where you can learn about and taste locally-produced olive oils. This family owned ranch showcases the art of sustainable farming while offering visitors a chance to sample high quality, handcrafted olive oils.

Travel tip: When it’s time for a meal (or a good night’s sleep) head to Steamboat Inn, a charming riverside restaurant along Highway 138. 

Overnight: Book a stay on the banks of the Rogue River at the historic Weasku Inn or Riverside Inn.

Situated at the southern terminus of this route, Ashland and the surrounding area offer more opportunities for outdoor and culinary adventures. The Pacific Crest Trail–the West Coast’s famous thru-hike trail, stretching 2,650 miles between Canada and Mexico–makes its debut in Oregon here as it winds its way through the Cascades. This is where hikers can find some of the best bang-for-your-buck access, where Mt. Ashland and the Cascade-Siskiyou National Monument offer easy access. 

Between Grants Pass, Medford and Ashland, the Rogue Valley Food Trail highlights over 40 local businesses, where visitors can sample everything from cocktails made with local spirits to small-batch chocolates. One must-stop is the Rogue Creamery, which holds the distinction of producing the “World’s Best Cheese,” for its flagship Rogue River River Blue. The trail also encompasses the scenic Applegate Valley, where visitors can experience the annual lavender bloom at Applegate River Lavender Farm and The English Lavender Farm.

There’s plenty to explore on your own, but if you’re looking for a local touch, book a wine tasting experience with Rogue Trotter Tours as they transport you through the Rogue and Applegate Valley AVAs–Oregon’s oldest wine growing region. 

Travel tip: Catch a performance during the Oregon Shakespeare Festival in Ashland, which runs from March through October. 

Overnight: Relax at Lithia Springs Resort– Oregon’s Mineral Waters Retreat, or a number of cozy bed and breakfasts and boutique hotels.

From Ashland, head northeast towards the Volcanic Legacy Scenic Byway-All American Road to Crater Lake National Park, the state’s only national park. 1,943 feet of crystal clear water fills the caldera of this ancient volcano, making it the deepest lake in the United States and the seventh deepest in the world. Along the way stop for a thrilling zipline adventure or calm water paddle with Crater Lake Zipline, or opt for a guided experience around the 33-mile Scenic Rim Drive in the park. Outfitters such as Explore Southern Oregon Tours offer tours with ample opportunities for hiking, picnicking, and sightseeing within the park. 

The Pinnacles and Plaikni Falls trails offer easy on-your-own strolls above the lake, but if you’re really itching to stretch your legs, the strenuous Cleetwood Cove trail leads hikers down to the only legal access to swimming and boating in the lake. There are two options for staying inside the park–Crater Lake Lodge and The Cabins at Mazama Village–but we recommend making reservations well in advance.  

Travel tip: Check road and weather conditions and park closures before you go—especially if visiting outside of summer. Snow can linger into late June, and the Rim Drive is typically only fully open from July to October.

Overnight: Crater Lake National Park, Crater Lake Resort in Fort Klamath, or Running Y Resort.

Take the scenic route to Bend from Crater Lake along the Cascade Lakes Scenic Byway, where you’ll encounter more volcanic views and crystal-clear lakes. The byway begins near Crescent Lake Junction, about 50 miles north of Crater Lake National Park’s northern entrance. This 66-mile route winds through the Deschutes National Forest, offering breathtaking views of snow-capped volcanoes like Mt. Bachelor, the South Sister, and Broken Top. Popular stops include Sparks Lake, Devil’s Lake, and Elk Lake, each offering opportunities for paddling, fishing, and hiking.

Midway along the Byway, make a stop at Mt. Bachelor to experience the thawed-out ski resort in its warm weather glory. Here visitors can enjoy stunning scenic chairlift rides,  “Ask a Ranger” US Forest Service interpretive talks (check availability first) or a high alpine hike. For the more adventurous, Mt. Bachelor is also a destination for downhill mountain biking and ziplining. 

Nestled in the high desert of Central Oregon, Bend is renowned for wide-open spaces and a thriving craft beer and culinary scene. The city offers a wealth of activities, with Historic Downtown Bend featuring over 325 diverse businesses and hosting a variety of events throughout the year. A visit to the picturesque Mirror Pond in Drake Park is a must, offering a peaceful escape in the heart of town. Pay your respects to Bend’s logging history with a trip to the Old Mill District–once home to two of the largest pine lumber mills in the world, the area has been transformed into a vibrant hub for shopping, dining, entertainment, and outdoor recreation. 

Central Oregon is also known for its craft breweries–over 30 in the area around Bend. Let the Bend Ale Trail be your guide to the locals’ favorite watering holes. 

Travel tip: The Cascade Lakes Scenic Byway is open during the summer and fall, typically from mid-May or June until late October or November, depending on annual snowfall. 

Overnight: Whatever your style, Central Oregon has the perfect stay—from cozy, budget-friendly motels to sprawling resorts. 

Educate yourself about central Oregon’s volcanic past at the Newberry National Volcanic Monument. This 54,000-acre monument features some of the area’s most unique geological features, such as the Lava River Cave, the Big Obsidian Flow, and the Lava Cast Forest. Tucked within the caldera are East Lake and Paulina Lake, twin alpine lakes that attract hikers, paddlers, and anglers alike. East Lake is renowned for its trophy-sized brown trout, while Paulina Lake boasts natural hot springs along its shore. Just beyond the lake, Paulina Creek Falls drops 80 feet over striking volcanic columns, offering a breathtaking sight.

Dive deeper into Central Oregon’s landscapes and heritage by visiting the award-winning High Desert Museum, Central Oregon’s natural living museum just 10 miles (16 kilometers) north of Sunriver and six miles (10 kilometers) south of Bend. The museum presents the region’s natural and cultural history with live animals, including an astounding birds of prey exhibit, as well as dioramas and breathtaking western exhibits and Native American art. 

Travel tip: Book a cave or volcano tour in Newberry National Volcanic Monument through Wanderlust Tours.

Overnight: Bend or Sunriver

The remnants of an extinct volcano, Smith Rock State Park rises dramatically from the sagebrush flats to greet travelers from far and wide. Juxtaposed with the Crooked River running beneath the cliffs, this beloved state park is a popular destination for hikers, climbers, and wildlife enthusiasts. Golden eagles, mule deer, and river otters frequent the park, which can be spotted on the family-friendly River Trail, a 2.5-mile stroll along the water. 

For your last night, stay in the charming small town of Sisters. Due to the community’s efforts to reduce light pollution, the town is an officially designated International Dark Sky Community. So don’t forget to look up and enjoy a clear, unobstructed view of the Milky Way. 

Travel tip: If you’re looking for an alternative to beer, sample small-batch spirits and cocktails at Cascade Spirits Tasting Room & Bottle Shop in downtown Sisters. For a wide variety of food offerings, head a few blocks over to the food carts at The Barn.

Overnight: Five Pine Lodge near downtown Sisters or Black Butte Ranch Resort just outside of town.