An Oregon Road Trip: Hiking, Camping, and Skateboarding Across the Beaver State

portland oregon
The best place to start your journey is in Portland. Courtesy of Elena Kuchko/Unsplash

As summer is coming to a close, the opportunity for sunny, warm out-of-town adventures is dwindling by the day. Whether you are interested in overnight trekking in the backcountry, floating rivers between campouts, or simply on the search for epic concrete skateparks to fill your days … Oregon offers opportunities to do it all.

However, planning a short, tail-end-of-summer trip to the beautiful Pacific Northwest might seem a bit overwhelming. The toughest part tends to be deciding where to start. Then comes the challenge of cramming in all the possible activities. Finally, figuring out where to finish your trip turns into a dilemma of its own.

Forget the pains of planning for this trip, we have worked out the kinks in advance and even left enough wiggle room to turn it into an adventure all your own. Here is our “How-To” guide for maxing out on the outdoors in Oregon in a single week.

portland oregon
Portland, in all its glory. Courtesy of Umit Aslan/Unsplash

Typical of a trip to Oregon, we start things off in Stumptown, a.k.a. Portland. We do not end there, though, so make the most of the infamous City of Roses as soon as you touch down. Check out the Rose Garden, taste the quality coffees, cross over the numerous structures that make up Bridge City and be sure to eat out for every meal – after all, since the rest of this trip will be spent mostly in the woods, we strongly recommend taking advantage of one of the United States’ foodie-est cities.

burnside skatepark
The legendary Burnside Skatepark. Courtesy of Bandita/Flickr

This is also your chance to check out Burnside, skateboarding’s most iconic D.I.Y. park. Even if the terrain at Burnside is not for you, it’s definitely worth a peek. From there you can skate any of the other recognizable skateparks such as Glen Haven, Ed Benedict or even Tigard (technically part of the Portland metropolitan area). The choice is yours, we’ve barely scratched the surface of possible places to skate in Portland.

Next stop is the Sandy River. Just outside of PDX heading east on Interstate 84 along the Columbia Gorge is one of Oregon’s laziest rivers for a float. Take two vehicles if you can, in order to shuttle your friends between starting at Dabney State Recreation Area and finishing at Lewis and Clark State Recreation Site, or stick out your thumb and show a smile for a ride back to the top once you’re done.

If you’re more interested in gazing at some water rather than jumping in, a stop at the famed Multnomah Falls is sure to boggle your brain with beauty. Beware, though, both the Sandy River and Multnomah Falls can become crowded in the summer due to their proximity to the city.

Lower Punch Bowl Falls
Lower Punch Bowl Falls. Courtesy of Jeff Hollett/Flickr

If you are looking for less of a crowd while checking out some waterfalls, try hiking the Eagle Creek Trailhead. This hike is easy to access – so we can’t promise you will have it all to yourself – and also offers amazing waterfalls to view (such as Punch Bowl Falls of Tunnel Falls) but only after you put in a little work on the trails. Regardless of what your choice is, if you can score some time at any location you won’t be disappointed and you will get your first taste of the outdoors to come for the rest of the week.

eagle creek trail
The colors you’ll see on Eagle Creek Trail are magnificent. Courtesy of Eli Duke/Flickr

Ultimately, after Portland, the next “major” city to stop at is Hood River. Located on the Oregon side of the Columbia River, Hood River is a must-visit stop while living it up outside in the Pacific Northwest. A world-famous location for kiteboarding (and only a 30-minute drive from Mount Hood) Hood River is a town full of fun-loving outdoors enthusiasts. Plus, it has one of the most unique skatepark designs incorporating gaps over a creek and winding paths between various sections.

Boneless by George Silver
Boneless by George Silver at Hood River Skatepark.

Perhaps before you reach Hood River (or after), camping along the Columbia Gorge is beautiful and plentiful. But beware, it can get crowded. If you don’t have any luck reserving a state-run campground then we recommend trying your luck on Bureau of Land Management (BLM) territory or a national forest for free camping in the forest. Be prepared to lock up your food at night from the small and large critters alike, as well as know how to responsibly dispose of all waste – please abide by the “Leave No Trace” Principles).

Depending on your prerogative, a short stint over to Washington’s side of the Columbia River can bring you to the town of White Salmon, next door to the Bingen Skatepark. This park is often empty and quiet but contains one of the most creative flows for a park of its size. However, if you are willing to wait on skating, the number of day-hikes and amount of terrain to explore around Mount Hood is guaranteed to gift you some beautiful silence as you wallow in nature.

Courtesy of Jimmy Beebe
Scenic portion of Bingen Skatepark.

The final “major” city on our recommended trip is Bend. If there was any other town in Oregon that rivals Hood River in the amount of outdoor enthusiasts that call it home, Bend might actually beat it.

If you want to hike or climb something, you have to hit the world famous Smith Rock. If it’s a small lake you are in search of, take a trip off the Cascade Lakes National Scenic Byway where you can find 14 different alpine lakes to enjoy along the 66-mile roadway. Camping out at these lakes is typically available, too. Be sure to check-in with campground officials unless you plan to take your overnight adventure off the beaten path.

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The majestic Smith Rock. Courtesy of Unsettler/Flickr

Or, maybe you’re feeling another skate session again after taking the day prior off the board. In that case, there are three skateparks in Bend – two of which (Ponderosa and Rockridge) are rather new and are easily capable of facilitating an all-day session.

At this point it is time to start packing all of your gear back into the luggage that you brought it in. But instead of driving all the way back to Portland for your departure home, utilize the Redmond Airport when booking your return travel. Only 20 minutes out of Bend, this airport allows you and your friends to float the Deschutes River right through the heart of town before flying home in the evening.

NOTE: Readers should plan ahead for their campground bookings as well as locating BLM territory or national forest areas that are suitable for camping. Don’t worry, though, there are a ton.

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