Western Skylight
Exploring the charming, old-west, high desert town of Sisters in Central Oregon
by Josiah Roe, Felipe Silva, and Ethan Balnap
We crest the Cascade Range just after dusk, watching the silhouettes of the three Sisters volcanoes dark against the fading light. I grip the steering wheel tighter as we dip into Central Oregon’s high desert for the first time. Bella presses her forehead to the window, tracing the outlines of pines and starlit sky.
By mid‑evening we roll into Sisters, Oregon, tired but brimming with excitement. We make our way to The Ponderosa Lodge, checking in under a sky freckled with the first stars. As we unload, Bella lets out a little gasp: a small herd of alpacas grazes lazily on the lodge grounds, and we greet the Muklashy family who are visiting on vacation and are enthralled with the creatures from South America.
We bid them farewell as we’re ready to stretch our legs, so we walk the length of Sisters’ main streets, spotting art galleries, western storefronts, and the gentle hum of evening life. Our dinner destination: Sisters Saloon.
Inside, the smell of wood and whiskey is warm in the air. We settle in for dinner with live music. Bella orders a mocktail; I have a whiskey neat. The musicians play gentle country‑blues, and we let the evening drift around us.
Later that evening we drive out to Pole Creek Ranch, equal parts active ranch and event space, just outside of town. Central Oregon has recently achieved status as an International Dark Sky Sanctuary, and tonight the heavens seem to lean in close.
We park on an old ranch road and lay back on our blanket, watching the Milky Way rise over the barn, ranch house, and the peaks of the Cascades. The lights of the old ranch, dim lanterns illuminating the distant barn, are an incredible juxtaposition to the stars above.
The following morning we set out for breakfast at Angeline’s Bakery. The air, even in summer, is crisp, and Bella beams when she sees the gluten‑free section: muffins, scones, and decadent-looking cinnamon rolls sit behind glass. She points at one and says, “Fuel for the hike.” We split a cinnamon roll (or try to), accompanied by strong coffee and fresh juice.
We drive a few miles south and west of Sisters to the Whychus Creek Trailhead for a roughly 6.4 miles round‑trip hike with about 660 feet of elevation gain to view the Wychus Creek Falls.
We ascend through volcanic rock and ponderosa pines, light filtering through branches. At about 1.8 miles in, a spur leads to the Whychus Overlook, a 0.9‑mile accessible loop perched atop cliffs with sweeping views.
From that vantage we look down at the creek winding through canyon walls, and beyond, the Sisters peaks. The trail then leads us closer to the water, where we catch glimpses of small waterfalls and the rush of water through lava‑touched rock.
Sisters is nearly completely ringed by public lands: forest, high desert, and rivers that carve their way through cooled basalt lava flows. The Whychus Trail feels like one of those quiet arteries into a wilderness that remains.
We head east out of the mountains and back into town and settle on Frankie’s (formerly Sisters Depot) for lunch. The place is run by Eryn, who named it after her French bulldog “Frankie,” often found lounging in the courtyard or the event space upstairs.
The outdoor patio is tucked away from the main street’s bustle and is a perfect quiet spot for a group of friends. Bella orders a beautiful salad, I have a sandwich, and we both sample a mocktail and a craft cocktail. We linger, watching locals and travelers drift past.
In the afternoon, we stroll through the historic part of town. Sisters began as a supply hub for sheep‑grazing ranchers crossing the Cascades. The name “Sisters” was shortened from “Three Sisters” by postal authorities in the 1880s. We pass heritage buildings, murals, greenspaces, and the sweet hum of a town that values aesthetics. We duck into galleries, browse quilt shops, and pause in shaded courtyard nooks.
Later, we drive to FivePine Lodge for their late afternoon happy hour. The resort, which just won “Best of the Best” for lodges in the country on TripAdvisor, in a remarkable collection of log cabins and buildings, including a brewery and movie theatre.
We wander the pine‑forest grounds, listening to creeks and birds, exploring the various cabins and buildings, which are nestled among trees and streams, and feel idyllic. We sip drinks on a porch, watching golden light filter through branches.
We walk back into town for dinner is at Ski Inn Taphouse & Hotel, which is famous for its BBQ & local brews. The historic inn building itself, which dates back to 1910, now houses a bar, restaurant, and renovated boutique hotel that captures the town’s rustic charm.
We rise early and make our way to Sisters Bakery. Through the window, we watch Spencer and his team work with dough, ovens, and the rush of early orders. The bakery supplies many restaurants across Central Oregon. The hum of activity, flour‑dusted arms, trays sliding in and out, it feels like the vibrant heart of the town.
Next, we head toward Long Hollow Ranch, a working cattle ranch dating back more than a century, still running a few hundred head of cattle. We meet goats near the barn, wranglers at the corral, and horses saddled for the morning ride. Our trail ride lasts about 90 minutes, winding along ridgelines with sweeping views of the high desert canyon where the ranch resides.
Afterward, we relax in the ranch’s Saloon, swapping stories, and learning that the ranch because of its location on the Willamette Valley and Cascade Mountain Military Road was historically a popular stop for travelers to stay, or to rest and water their animals.
For lunch we drive to Faith Hope & Charity Vineyards, named for the Three Sisters peaks’ monikers. The 15‑acre vineyard grows cold‑hardy varietals like Marquette, Leon Millot, Frontenac, LaCrescent, and LaCrosse, ideal for the high desert climate.
We sit outside with a wood‑fired pizza and a flight of wine, watching the peaks glow in the distance.
We learn from the owners about The Big Ponderoo: Sisters’ summer music festival featuring Americana, bluegrass, and folk, and we decide to stay for another night.
It is a perfect end to our trip: for a weekend each June, the quiet town turns electric with sound: fiddles echo off the old storefronts, families dance in the grass, and the mountains frame every stage. It feels like the perfect reflection of Sisters itself: small-town charm under a big, open sky.
