Once a sleepy little town that most people wouldn’t be able to pinpoint on a map, Bend, Oregon, is now a mecca for those chasing their outdoor pursuits. Hugging the Deschutes River, and home to the last Blockbuster in the world (no, really look it up), Bend is a place full of great places to eat and drink, friendly faces, and a culture that will leave you wanting more. While skiing, hiking, camping, and trail running are plentiful, the mountain bike community comes alive every summer season.
Bend has an extensive singletrack trail network right out the front door, nestled in the Deschutes National Forest. Over 570 miles of trails hold terrain for beginners and experts alike. A local favorite is Whoops to Lower Whoops, which involves a four-mile climb rewarded with a blissful downhill full of flow, speed, berms, and playful jumps. It’s a must!
Unlike a lot of the other riding in Oregon, the trails in Bend have a tendency to get a bit dusty. Because of its dry climate, Bend is an awesome early season bike destination for people looking to escape the snow or rain. If it’s too hot to ride, you can float, fish, or surf the Deschutes River, hit a local brewery, or enjoy some fresh local eats.
If you decide to visit Bend, rent a small Airbnb downtown or camp in the Deschutes National Forest and enjoy quick access to local culture, good vibes, and memorable trails.
Tiddlywinks and Funner
Upper and Lower Whoops
Mt. Bachelor Bike Park
Oregon has 362 miles of rugged Pacific Ocean coastline, which means plenty of options for surfing. It’s also closer to the North Pacific Ocean, where storms begin in the winter months and produce waves across the entire west coast. These storms bring along all the wind and rain that keep Oregon’s forests happy and the trails muddy, so patience and a good pair of boots always come in handy when you’re exploring Oregon’s surf spots.
If you’ve never surfed before or want to brush up on your skills, Oregon Surf Adventures offers amazing programs to get people in the water and stoked on surfing, like kids’ camps all summer and adult private lessons. They’ve been based out of Seaside, Oregon for the past 10 years, and we know from experience that you can’t beat local knowledge.
If you opt to go explore Oregon’s surfing on your own, Highway 101 runs the length of the coast, and there are many state parks and beaches with year-round camping available. Many of the best places to surf—like Indian Beach, Short Sands, and Pacific City—are in or around these parks.
If the waves don’t cooperate, take a walk down Cannon Beach or head to the Tillamook Cheese Factory, a local dairy co-op that makes some of the best cheese and ice cream on the West Coast. Kelly’s Marina offers great crabbing and fishing off the dock or via a boat rental from the marina. Even if you don’t catch much, Kelly’s serves beer and great seafood lunches right on the bay.
The coastal town of Seaside, Oregon is home to one of two trailheads that access the Tillamook Head Trail. This astounding coastal hike, named the Tillamook Head Traverse, brings you six miles (each way) from Seaside to Indian Beach and features all the classic Oregon coast views of rock cliffs, ocean waves, spruce forests, and even an old lighthouse with a remarkable story.
The Tillamook Head Traverse is popular as both a day hike and quick overnight backpacking trip. The maximum elevation of the trail is 1,248 feet, with markers along the way to indicate the changes in elevation. Be prepared for cool, rain showers that are common here by bringing along a good rain jacket and wearing mid-ankle hiking boots.Starting from the Seaside, it’s four miles to Hiker’s Camp, which has three WWII-era bunkhouses, a fire pit, an outhouse, and a covered picnic table, making it a well-equipped place to spend the night. If the bunkers are full, there is plenty of space for tents as well. If you plan to spend the night, you must also haul in your own water.
Indian Beach is another two miles past Hiker’s Camp. Once you hit the beach, you’ve completed the six-mile hike from the Seaside trailhead. You can either choose to head back to Seaside the way you came or continue walking the beach for as long as you please.