Great Getaway: Sisters, Oregon


When pulling into Sisters from the West you’re greeted by a main-street cowboy town filled with local shops, western storefronts and lots of charm. But as you reach the far end of that main street (it’s actually U.S. Hwy. 20,) something different emerges. There’s some upscale lodging, a brewpub, movie theater and spa that gives Sisters a whole new attitude. At the heart of that transformation – the Five Pine Lodge, which has quickly become a destination for families looking for something different and for couples looking for a enchanting romantic retreat.  The Five Pine campus is a perfect home base for your Central Oregon summer vacation.

And while yes, you could go your entire visit without leaving the campus – we’d advise against that.

Five Pines Lodge

Day One

You don’t have to go very far away from Sisters to experience everything that is Central Oregon. Day one starts off on a relaxing note at Aspen Lakes Golf Course. Don’t consider golf “relaxing?” Well, then you’ve never experienced Central Oregon golf. At Aspen Lakes, wayward shots are sometimes swallowed by unique red cinder bunkers that will make you forget you’re in a hazard. And from the tee box of many holes, your target will be a majestic, snow-capped mountain in the distance. The views, not your score, is what you’ll remember most about Aspen Lakes.

View of lake, greens and Cascades in Sisters, Oregon

After golf, its back to your cabin at Five Pine where you’ll fight over who gets the soaking tub first – or, better yet, you get romantic and compromise. Relax in your room with a game of chess before meeting up with other guests outside for the nightly beer and wine reception. It’s then just a short walk downtown for some window shopping and dinner.

Five Pine Lodge room interior near Bend, Oregon

Day Two

Today starts with a classic breakfast at the new Cottonwood Cafe. It’s all the fuel you’ll need if you’re heading out on two-wheels not to be bothered by cars on one of Oregon’s most scenic roads. The McKenzie Pass Scenic Bikeway starts in Sisters and takes cyclists up to a world all its own. For a month or so each spring, the road is only open to cyclists as road crews continue clearing the snow for car travel later in the summer. It’s a challenging 15 mile ride up the road to the Dee Wright Observatory, but the scenery is worth the effort. Beyond the giant snow banks winter left behind is a sea of lava rock creating a moonscape unique to Central Oregon. The road is currently open to cars and cyclists, so be alert regardless your mode of transportation.

Cyclist on the McKenzie Pass Scenic Bikeway near Bend, Oregon
Cyclist on the McKenzie Pass Scenic Bikeway – Photo Credit: Aaron Theisen

After the ride you make a bee line to the Shibui Spa just a few steps from your cabin. A dip in the hot tub and a massage is just what the doctor ordered on this stress-free getaway.

Soaking tub at Shibui Spa in Central Oregon

Tonight it’s just a six pack of Central Oregon craft beer and a pizza while you hang out in your room – a much deserved evening of relaxation after a full day of pedaling.

Day Three

As hip and happening as Sisters is these days, it (thankfully) hasn’t shed completely its small-town feel.  That’s never more evident every June during the Sisters Rodeo. Dubbed “The Biggest Little Show in the World,” the rodeo is five days of rip-roarin’ fun that includes professional Xtreme bull riding and several family focused events like the Buckaroo Breakfast on Sunday.  After a late breakfast downtown, you hit up the matinee rodeo performance under the sun at 1 p.m.

Sisters Rodeo

When the dust settles you head back to campus and Three Creeks Brewing Co. – which you’ve had your eye on since you arrived in town. You split an appetizer of spicy cheese and crawfish dip over a couple of pints of Knotty Blonde and Hoodoo Voodoo IPA while you wait for the main course.

3 creeks outside

One final night at your upscale cabin on campus and this Central Oregon vacation is a wrap. You head back West through the main-street cowboy town knowing the best of both worlds is there waiting for your return.

Visit Central Oregon
Visit Central Oregon
Visit Central Oregon is the "Official" Tourism Information Resource for Central Oregon, including the communities of Bend, Sunriver, Redmond, Sisters, La Pine, Madras, Prineville, Crooked River Ranch, Terrebonne, Culver, Warm Springs, and Black Butte Ranch.
Visit Central Oregon

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