: Painted Hills by Christian Heeb

Cool Season Adventures

Now is the time for a winter road trip.
November 20, 2017

Lindsey Murphy, Host | Jesse Larson, Videographer | Jon Shadel, Producer


“Sunbreaks” — this charitable word in the Pacific Northwest lexicon tells you something about the climate. Yes, Oregon sees its fair share of gray skies, no denying it. But here’s a local’s secret: The changing weather of fall and winter means even more opportunities for adventure.

Hit the road this time of year and you’ll find trails to gushing waterfalls, anglers casting lines in rushing rivers, winemakers stoking fireplaces in their tasting rooms, whales waving from the Pacific and ever-changing landscapes that leave you gobsmacked.

Ready to trade the humdrum for some fresh thrills? Take an ambitious tour through all seven regions of Oregon to see everything that makes the cooler months so cool. But you don’t have to do it all at once. Check out these highlights to start planning your own getaway.

Road rules: The weather can change in the course of a few hours in late fall, winter and early spring; pack layers, check road conditions at TripCheck.com, and call ahead to make sure parks and attractions will be open. No matter where you go in Oregon, lay off the horn, say a friendly word to everybody and leave no trace.


Play the game

OK, we admit it — nothing beats a real-life road trip. But “Travel Oregon: The Game” comes close. Inspired by the classic you played in elementary school, this mobile- and desktop-ready game serves up many of the seasonal adventures featured here, but in vintage 8-bit glory. Play it now.


Watch for Whales

If you had to pick a mascot for the Oregon Coast, you might choose the gray whale. Each winter some 20,000 great grays swim along the shore — south from Alaska’s Bering Sea to the warm-water lagoons of Mexico’s Baja California — then retracing their 12,000-mile migration north in spring. Spotting them spy-hop, breech and blow ranks high on Pacific Northwest bucket lists for a reason: Few wildlife encounters rival the moment you see the magnitude of these whales, which grow to 50 feet and weigh around 40 tons, rising from the Pacific.


Need to know

Going whale watching requires little more than binoculars and a prime vantage point. The town of Depoe Bay dubs itself the “Whale Watching Capital of the Oregon Coast,” and there you’ll find the Oregon State Parks’ Whale Watching Center, where experts can tell you anything about these gentle giants.

When to go: A population of whales lives along the Oregon Coast year-round, but visit during two Whale Watching Spoken Here weeks for the best chance of a sighting. In-the-know state park volunteers man two dozen designated sites in winter (Dec. 27-31, 2017) and spring (March 24-31, 2018).


Sip and Swirl


Glossy magazines typically depict oenophiles dressed in sport jackets and sundresses prancing through light-flooded vineyards. Lose the suit coats and you’ve got a picture of summer in the Willamette Valley, named Wine Enthusiast’s 2016 wine region of the year. But if you ask a winemaker, they might surprise you by suggesting a cooler-months visit. After they finish off fall harvest by plucking the last grapes from the vines, vintners kick off their muddy boots and pop open a prized bottle to celebrate a job well done. The slower pace means you can savor the whole wine-touring experience a little longer — linger in family-owned tasting rooms, chat up a relaxed winemaker and sneak a few extra sips.


Need to know

The valley consists of several distinct AVAs (American Viticultural Areas), which together contain nearly 600 wineries. The greatest concentration lies at the northern end. Head south for less-trafficked roads and generally quieter tasting rooms. Remember, go with a designated driver or join a guided tour.

When to go: Most tasting rooms stay open year-round, especially the state’s largest producers, such as King Estate. Some smaller wineries keep limited winter hours or may open only by appointment. No matter the wine loop you choose, call ahead to ensure the wineries will be open upon arrival.


Tour an Old West Town

Oregon’s small towns brim with relics of the Old West: vestiges of 19th-century pioneers and the new lives they built here. Few communities have preserved that history better than the teensy burg of Oakland, a twee town of just 900 tucked in Southern Oregon’s Umpqua Valley. Its handsome downtown retains the original brick structures built in the 1880s and 1890s, and it was the state’s first historic district recognized by the National Register of Historic Places. A self-guided Historic Walking Tour encompasses more than 80 sites — old-time storefronts, antique shops and Victorian-era homes. Pick up a copy of the map at the Oakland Museum, spend an afternoon strolling the town and don’t forget to pop into Tolly’s Grill & Soda Fountain for a thick milkshake.


Need to know

Just north of Roseburg, Oakland is a quick detour off I-5, but you’ll want to budget a few days to explore the surrounding area, including fly-fishing on the North Umpqua River, hiking trails in the Umpqua National Forest and touring award-winning Umpqua Valley wineries.

When to go: The holiday season is one of the best times to visit Oakland. The town lights up with Americana charm, and you can find plenty of vintage gifts in a handful of local shops. Timely fact: Your Thanksgiving bird might even trace its lineage here. The town, once nicknamed the “Turkey Capital of the West Coast,” is where the broad-breasted bronze turkey was first developed.


Cast a Line

Frank Sinatra didn’t sing it, but it’s true: If you can catch a fish here, you can catch a fish anywhere. Fishers shiver at the river’s name, dubbing the North Umpqua in Southern Oregon the “graduate school of steelhead fly-fishing.” And for good reason: Some 30 miles of fly-fishing-only water plus the legendary power of its native steelhead land it on many anglers’ bucket lists. Newbies also find reason to love the river, especially in winter, when it hosts one of the strongest steelhead runs in the state. Why not start at the top?


Need to know

First-timers should seek out the expertise of a local guide, who knows the river and can supply all the necessary gear. Pros can check out even more winter fishing in Southern Oregon. And grab grub, licenses and tackle at the historic Steamboat Inn, a riverside favorite among generations of anglers.

When to go: Southern Oregon lures fishers to its pristine waterways in every season. You can fish the North Umpqua year-round, though species vary. Plan on January through March for winter-run steelhead. For up-to-date fishing reports and regulations, consult the Oregon Department of Fish and Wildlife website. Check United States Forest Service alerts as recent forest fires may have caused closures to certain access points.


Hike to a Waterfall

Central Oregon sits in the middle of rugged territory primed for adventures — from rafting to skiing to snowshoeing to mountain biking, you name it. And through the center of it all flows the treasured Deschutes River. An ever-expanding, multimodal trail system, aptly named the Deschutes River Trail, winds for miles through ponderosa pines and along the banks of the rushing river. For a quick immersion, hit the 1.2-mile there-and-back trail to Benham Falls, which drops 25 feet in a fury of whitewater rapids. As with every hike in Oregon, you’ll want to end your day at the pub; pop into one of the dozen-plus craft breweries on the Bend Ale Trail.


Need to know

Find the trailhead at the end of Forest Service Road 9702; those of limited mobility can park at the Benham Falls West Day Use/Trailhead for immediate access to the falls.

When to go: The all-abilities-friendly trail sees a lot of traffic in the warmer months, especially on the weekends. Dress up in layers for a late-fall and winter trek, and visit on weekdays for more seclusion. Dog owners can unhook the pup’s leash from September 15 to May 15.


See a Prehistoric World

Big skies soar overhead in Eastern Oregon, where a short drive on winding highways sees the windswept landscape dramatically transform. It’s a world of ever-changing contrasts with snowcapped mountains rising in the distance. The gray clouds of winter make the rustic hues of the Painted Hills pop. The stratified colors — sunburned yellows, deep oranges and muddy reds — are fossilized soils representing millions of years of history. It’s one of three distinct units in the John Day Fossil Beds National Monument, a massive area bearing fossils from the Age of Mammals. Better understand this immense geological history by visiting the Thomas Condon Paleontology Center.


Need to know

Emphasize “sparsely populated.” The Painted Hills, one stop on the Journey Through Time Scenic Byway, sits in a remote area with limited cell service. Fill up your tank whenever possible, as services in this part of the state are limited. Find lodging in the surrounding communities.

When to go: You can visit year-round, though plan a fall, winter or early-spring trip to take advantage of the moisture, which brings to life the colors of the hills. Rise early to catch the morning light. Snowfall can make trails icy, so check the weather before you go.


Explore a Ghost Town

Hold your breath and you’ll hear only the hum of wind rustling through a sea of golden grass. It feels haunting — that eerie stillness of a place no longer animated by the drama of those forging a life in the American frontier. Oregon’s many ghost towns are like time capsules, and each one tells its own story. The demise of Hardman in Eastern Oregon is a tale of poor luck: It once was a lively stagecoach hub, home to 900 people at its peak and complete with a newspaper, post office, hotel and saloon. The town died fast when the railroad bypassed it. Today it has a dozen or so decaying structures to admire, including a lodge on the National Register of Historic Places.


Need to know

The rule of thumb when exploring ghost towns is to take photos and nothing else. Don’t assume the abandoned-looking buildings are actually abandoned. In Hardman, a handful of residents still live amidst the decaying town. They’re a friendly bunch and reportedly enjoy answering questions about the area’s history.

When to go: There’s no peak season for ghost-town exploring, but photographers love to visit in the cooler months of fall and winter. The overcast weather adds a forlorn sense of mystery to the images they capture.


Try Mountain Biking

Get ready to kick up some mud. The brisk air and ever-present drizzle of Cascade Locks makes the relatively new easyCLIMB Trail a little wet and sticky in the cooler months — just the way loads of bikers like it. The Columbia River Gorge ranks high in the minds of pro riders due to its expansive network of trails. But as its name implies, easyCLIMB targets new and moderately experienced riders. Built by the Northwest Trail Alliance on a mossy, forested headland, the 2-mile loop trail also welcomes hikers to take in the serene views here of the mighty Columbia River.


Need to know

A kiosk at the parking area gives first-time riders a sense of what the trail offers. Riders will find a cluster of cycling shops offering rentals in Hood River; half-day and full-day rentals include helmets. Call ahead to reserve a bike.

When to go: Mountain biking in Oregon is a year-round activity, though fall tends to be peak season in the Gorge and around Mt. Hood. Many trails close for the winter; easyCLIMB offers year-round riding, though consult weather reports before setting out. Local bike shops are an especially helpful resource.


Meet the Brewer

The best Oregon adventures conclude at a brewpub. And did you know Portland has more breweries than any other city on earth? More than 100 in the metro area have earned it the nickname “Beervana.” Today’s seemingly endless varieties of beer styles stem from the pioneering work of early ’80s upstarts such as McMenamins, which rescues historic structures like the Kennedy School and converts them into iconic pubs and theaters. McMenamins, and many other breweries, offers behind-the-scenes tours of its facilities. Don’t miss the opportunity to meet the beer-obsessed people — and not only bearded dudes — who tirelessly craft each pint you down.


Need to know

You don’t need a guide to tour the dense beer scene in Portland; set out on foot or map out your own bike-and-brew tour. Or join guided tours — on foot, by bike, by bus and more — to connect with other beer-obsessed travelers and share a few pints together.

When to go: It’s always beer o’clock in Portland. But the cooler months have perks: Late fall brings the celebrated Holiday Ale Festival to Pioneer Courthouse Square, where breweries pour beers brewed exclusively for the event. And all over the city, winter sees taps go dark with an enticing variety of stouts, porters and more.


About The

JD Shadel
JD Shadel is a queer writer, editor and producer whose work appears in The Washington Post, VICE, Fodor’s Travel, The Atlantic CityLab and many others. When not hunched over a keyboard in one of Portland’s many cocktail bars, they hit the road in search of Oregon’s emptiest trails.