Southern Oregon is an underrated road trip destination during the fall when the weather begins to cool off and the summer’s forest fires start dwindling. The roads through this area are often winding, remote, and incredibly scenic, and you’ll often have areas all to yourself.
In this area, you’ll find Oregon’s only national park, towering redwood forests, and some of the most beautiful stretches of coastline on the entire west coast. The scenery isn’t the only reason to make this trip, as you will also be treated to some of the region’s best cheese, fresh seafood on the coast, and criminally underrated wineries scattered.
So, let’s pack the car and head out to explore this beautiful corner of Oregon.
Crater Lake
Oregon’s only National Park, Crater Lake, is a must-visit destination. Its impossibly blue waters, stunning mountain scenery, and opportunities to explore the unique natural landscapes of this area make this worthy of stop any time you’re in the area.
If you want the ultimate national park experience, try booking a room at the historic Crater Lake Lodge. Here, you can spend the night in one of their cozy rooms, wake up to one of the best views in the entire region, while enjoying your morning coffee.
Summer Lake Hot Springs

From Crater Lake we’ll head east to the remote town of Summer Lake and Summer Lake Hot Springs. These natural hot springs rise up from the ground next to Summer Lake which, depending on the season, can be a lake or a dried up playa.
The rustic hot springs feature both camping areas and cabins for rent and renting one or the other is required to soak in the springs as they are available to overnight guests only.
If you’re looking for a unique dinner opportunity in the area, check out the nearby Cowboy Dinner Tree, which offers a ranch-style dining experience.
Ashland, Oregon
After a rejuvenating night at the hot springs, it’s time to head back west to the I-5 corridor and the southern Oregon town of Ashland. This oasis in the mountains is best known for its annual Shakespeare Festival, which attracts hundreds of attendees each year.
That isn’t the only reason to visit this southern Oregon gem, though. The city’s downtown is as nice as they come, and the trails leading up into the hills around town make for splendid hiking.
If you’re looking for some outdoor adventure during the summer, head to nearby Mt. Ashalnd, which is open on the weekends for mountain biking, disc golf, and hiking.
Rogue Creamery
For most visitors to Oregon (and even locals, too!), the cheese that comes to mind when they think of Oregon is Tillamook. And how couldn’t they? This cheese is everywhere!
But did you know that a small cheesemaker in southern Oregon took home the gold in a worldwide cheese competition for the best cheese in the world?
That cheese was Rogue River Blue, and it came from Rogue Creamery, which is located just outside of Medford in Central Point. We can attest that all of the blue cheeses from Rogue are out of this world.
At their cheese shop, you can taste the different cheeses they produce, buy a picnic pack, or grab a sandwich for lunch.
If you want to see more of their operation, you can also visit their dairy farm in Grants Pass, which has a cheese stand where you can pick out some of their award-winning offerings.
Jacksonville, Oregon
Just outside of Medford sits one of Oregon’s most underrated towns – Jacksonville. As soon as you arrive in this historic town you’ll feel like you’ve been transported back in time with its well maintained 19th-century architecture lining the downtown core.
We recommend spending an afternoon wandering through downtown and visiting its numerous boutiques, cafes, and wine-tasting rooms.
If you’re looking for a more in-depth tour of the town, then check out the trolley tours, which run on the hour from late spring through mid-fall.
Southern Valley Wineries
Oregon is famous for the Willamette Valley and its stunning Pinot Noirs. But did you know that southern Oregon is also home to an impressive wine scene that is quickly gaining national notoriety?
This region is hotter and drier than the valley to the north, which means it specializes in Cabernet Sauvignon, Syrahs, Tempranillo, and other bold red wines.
A visit to the southern Oregon wine country means fewer crowds, lower prices, and a more enjoyable wine-tasting experience where you can sit down and relax rather than hustle through a pre-booked appointment.
Rogue River Jetboat Excursion
Experience the beauty of the wild and scenic Rogue River on a thrilling ride aboard a jet boat.
For those who don’t know, these boats have a shallow draft and can quickly accelerate, bank, spin, and power through whitewater that will leave guests aboard the boat soaked (that’s all part of the fun!)
There are a number of different tours out of Grants Pass, ranging from a couple of hours to all-day excursions that will take you through narrow canyons and to a backcountry lodge for lunch or dinner.
There are plenty of ways to see this incredible river, including hiking or rafting, but a jet boat tour is the fastest option for those on a time crunch. Either way, this beautiful area is not to be missed!
Oregon Caves National Monument
Found deep in the Siskyou Mountains, the Oregon Caves National Monument is home to a cave system that is unlike any others found in the state.
While Central Oregon is known for its huge number of caves these caves are all empty lava tubes with minimal cave formations.
Oregon Caves National Monument, on the other hand, is a more “traditional” cave system where you can expect to see impressive mineral formations, an impressive network of caves, and, hopefully again one day, the Chateau, where you can sit down for a meal inside a rustic lodge.
Jedediah Smith Redwoods State Park
As you make your way down Highway 199, you have no choice but to enter California before making your way back up the coast and into Oregon.
We might as well capitalize on this detour though and make a visit to the stunning coastal redwoods that tower over this area.
Jedediah Smith Redwoods State Park sits at the confluence of Highway 199 and the turnoff to get back onto Highway 101. This makes it a great place to stop and head out into the forest for a hike.
Head to the Grove of Titans trail, where you can walk amongst some of the largest trees in the park along an elevated boardwalk. The boardwalk makes the trail both ADA accessible and protects the tree’s root systems from being damaged by the thousands of visitors who come to this area every year.
Brookings, Oregon
Just up the coast into Oregon, you’ll find what is locally known as the Oregon Coast Banana Belt. Here, the temperatures remain far warmer than anywhere else along the coast, which makes this area a popular retirement destination.
The incredible coastline and views certainly don’t hurt this town’s popularity either.
Because Brookings is so far from major population centers, this area sees far less tourist traffic than the northern sections of the Oregon Coast. This means you’ll have plenty of room to spread out in town and take in the views rather than sitting in traffic jams and fighting for a parking spot.
Don’t miss Harris Beach State Park on the north side of town for its beautiful beaches and sea stacks.
Samuel H. Boardman State Scenic Corridor
Located along a 12-mile stretch of coast between Brookings and Gold Beach, Samuel H. Boardman State Scenic Corridor is one the prettiest and wildest sections of the entire coast.
Along the drive, you’ll find numerous turnouts that lead to secluded beaches, natural arches, and trailheads that will take you off the highway and into nature.
Plan for at least half a day, but preferably more, to make this 12-mile drive.