Mountains, desert and waterfalls: A points-fueled autumn road trip through Oregon’s natural wonders

Come leaf-peeping season, East Coast destinations like Vermont and New Hampshire tend to steal the spotlight. But if you’re looking for a stunning combination of mountains and foliage — not to mention cascading waterfalls, craggy canyons and high desert vistas — there’s a destination across the country that deserves your attention: Oregon.

While the Pacific Northwest has a reputation for rain, it’s unfounded throughout much of the state. Bend, for example, is part of a desert microclimate that on average sees less than an inch of rainfall each October. Even the substantially wetter Portland tends to see some perfectly sunny days in October, and when precipitation does arrive, it’s typically nothing to be afraid of, presenting as mist or drizzle rather than a plans-scuttling downpour.

If that sounds manageable, read on for an itinerary that will take you past several of Oregon’s natural wonders set against a backdrop of vibrant autumn hues — and if not, file it away until you’re ready to plan for spring and summer adventures.

Oregon road-trip planning

This itinerary starts and ends in Portland and passes through the cities of Hood River and Bend. All these cities have everything you’ll need, including supplies, internet access and gas or electric vehicle charging.

In between, though, you’ll cross over mountain passes and through some more remote areas where cell service is scarce, meaning it’s a good idea to download any maps, music and other information you might need ahead of time.

If you want to really lean into the Pacific Northwest ethos, this road trip is very doable in an electric vehicle. A single full charge can get many EVs through each driving day, and should you need to top up, charging stations are plentiful throughout the region. To save time and make things more convenient, opt for overnight accommodations that offer EV charging.

Related: The ultimate guide to road-tripping with an electric car

Budgeting your time

While the drive times are less than four hours between each set of overnight accommodations, if you want to make stops along the way, I recommend allotting a good part of each driving day to the journey.

Between drives, there’s plenty to do in each city and its environs, particularly for outdoor lovers. A full week for this itinerary will give you time to explore each destination at a comfortable pace.

Getting to Oregon

Portland International Airport (PDX) is an accessible (and beautiful) international airport with abundant rental car options and nonstop flights to several major U.S. cities, thanks, in part, to its status as an Alaska Airlines hub.

Because cross-country airfare can be costly, particularly during the summer, an Oregon trip may be a good occasion to use your points and miles. If you’re eyeing Alaska flights and don’t have Atmos Rewards points on hand, remember that you can often book Alaska awards through Oneworld partners American Airlines and British Airways.

The best months to visit Oregon

The state gets most of its precipitation in the winter months, making spring through fall the best time to visit.

October offers a gorgeous display of fall colors, typically accompanied by pleasant temperatures. July and August, on the other hand, are the most reliably sunny months, and they provide opportunities for swimming in Oregon’s rivers and lakes.

The one caveat is that the state — particularly drier areas like Bend — sees some wildfire smoke every year that’s impossible to predict and can show up as early as July. If avoiding air quality issues is your main concern, plan to complete your trip by the beginning of that month.

Portland to Hood River

After landing in Portland and picking up your rental car, the journey begins with a drive through the ultrascenic Columbia River Gorge on Interstate 84. Stretching 80 miles between the Portland metro area and The Dalles, this spectacular river canyon delivers vista after vista of dramatic cliffs and rushing waterfalls.

The first day’s drive will take you as far east as Hood River, a city of 8,000-plus that’s best known for its world-class windsurfing conditions. But there are a couple of stops you may want to make on your way to Hood River.

Troutdale

Just over 15 minutes into the drive, you’ll hit Troutdale, home to a couple of food-and-drink options worth pulling off the highway for. If you’re in need of a pick-me-up, head straight to Good Coffee in Troutdale’s historic downtown. Good has locations all over Portland and neighboring Beaverton, but this one doubles as a roastery. It’s a perfect stop for a drink and a pastry.

Nearby, Sugarpine Drive-In serves up vintage vibes on the banks of the Sandy River. Originally built as a gas station in the 1920s, it’s now a destination restaurant that draws massive crowds on summer days thanks to its soft serve and barbecue. Fortunately, the line moves quickly — and the food is worth the wait.

Multnomah Falls

Located right off I-84, the towering Multnomah Falls is a must-see Columbia River Gorge attraction. At 620 feet, it’s Oregon’s tallest waterfall and most-visited site. Take it in from the viewing platform, or walk up to the footbridge for a different vantage point. If you’re feeling adventurous, cross the bridge and continue up the 11 switchbacks to the top, where you can look down at the falls from above.

Note that summer visits (typically from late May to early September) between 9 a.m. and 6 p.m. require a timed-use permit that covers one vehicle and its passengers. It costs $2 to reserve on Recreation.gov, and you show it on your phone to an attendant between the parking lot and the falls. These do tend to sell out for popular slots, especially on weekends, so reserve in advance if you can.

Exploring Hood River

From kayaking to kiteboarding, opportunities to get out onto the Columbia River are nearly endless in Hood River. While the river itself can be rough thanks to the area’s famous winds, there are plenty of protected inlets perfect for boating, swimming and wildlife watching.

If you’d rather stay on land, check out the city’s charming downtown, grab food at a food truck by the river or, in the spring, view a carpet of wildflowers in Mosier, just a few minutes’ drive to the east. Hiking trails abound in the Columbia River Gorge area for something a little more active.

Beer and wine are big in this corner of the world. Hood River and White Salmon — just across the river on the Washington side — have several breweries between them, including the standout pFriem Family Brewers. Meanwhile, the Gorge is an up-and-coming wine destination, with Loop de Loop Wines, AntiChe Cellars and others within easy driving range.

Dozens of fruit stands and pick-your-own farms in the Hood River Valley make up the nearby Hood River Fruit Loop, which makes for a fun drive in the summer and fall.

Where to stay near Hood River

Until recently, the entire Columbia River Gorge area lacked an overnight option for points travelers, but that all changed with the addition of Under Canvas Columbia River Gorge. Located just across the Columbia River on the Washington side, Under Canvas, as a part of Mr & Mrs Smith, offers a glamping experience bookable with World of Hyatt points.

If you’re new to glamping with Under Canvas, expect stylish tented accommodations with luxurious touches like in-room showers, gas fireplaces and comfortable bedding. Amenities like a communal fire pit, nightly s’mores, board games and live music make it a cozy, family-friendly place to spend your evenings. Rates start at $274 or 20,000 World of Hyatt points per night through this October, and the property closes for the season Oct. 27.

Hood River to Bend

On this leg of the trip, you’ll witness the spectrum of Oregon’s microclimates, first driving through the dense, green Mount Hood National Forest and then past its glacier-covered namesake before emerging into the high desert of central Oregon.

As you leave Mount Hood in the rearview mirror, you’ll come upon Mount Jefferson and, finally, the Bend-area landmarks of The Three Sisters, Mount Bachelor and Broken Top. If mountain views are your thing, you’re in for a treat.

Little Crater Lake

Little Crater Lake is a bit of a misnomer. Geologically, it has little in common with the much larger lake it’s named for, which was formed by the collapse of an ancient volcano. But this crystal-clear, 45-foot-deep pond — formed by dissolving limestone and fed by an aquifer that keeps it 34 degrees year-round — is still worth a stop; you have to see it in person to believe how blue it really is.

Little Crater Lake is a short detour off of U.S. Route 26, the highway that will take you all the way to Bend. Park at Little Crater Lake Campground and follow the flat, barrier-free trail through a meadow for about 800 feet until you reach the viewing deck.

Smith Rock State Park

As Smith Rock State Park comes into view out your driver’s side window, you may for a moment think you’ve landed on the moon. Covering 650 acres, it’s characterized by striking red rocks made from compressed volcanic ash. One of Oregon’s seven natural wonders, it’s a landscape unlike any other you’ll find throughout the state.

The park gets beautiful foliage in the fall, and the combination of autumn leaves and high desert makes it a unique place to view fall colors. October and November temperatures are also much better suited to taking advantage of the many hiking and rock climbing opportunities inside the park, which can reach 100 degrees in the summer.

Exploring Bend

Bend’s proximity to spectacular nature and four-season outdoor activity makes it an attractive place to visit, and you’ll easily find enough to keep you busy here for a few days.

Opportunities for outdoor recreation are everywhere you look, including the center of town; the Deschutes River runs right through Bend’s Old Mill District, a shopping and entertainment hub. Depending on the season, you’ll see locals floating the river on inner tubes or walking along the adjacent Deschutes River Trail.

Further afield, Cascade Lakes Scenic Byway is a gorgeous drive through the mountains, and its many lakes provide places to swim or boat.

But Bend isn’t just for nature lovers. There’s plenty to enjoy in the way of shopping, dining and, in the warmer months, live music at the riverside Hayden Homes Amphitheater. Beer enthusiasts, in particular, are in for a treat, with more than 30 breweries to explore along the Bend Ale Trail.

If you have extra time in the area, consider a day trip to Crater Lake National Park, which might be the most beautiful place in the Lower 48. The trip takes an hour and a half each way.

Where to stay in Bend

Bend has a handful of hotels throughout its major areas that you can book with points. The Newberry Hotel Bend, a member of Hilton’s Tapestry Collection, is within easy walking distance of downtown Bend’s shopping and dining options. October rates start at $184 or 57,000 Hilton Honors points per night.

My personal go-to in the area, though, is the Residence Inn by Marriott Bend for its easy proximity to Hayden Homes Amphitheater and riverside recreation. It’s on the nicer side for a Residence Inn, and I find it’s a great place to use Marriott’s 35,000-point free night certificates. October rates start at $158 or 31,000 Marriott Bonvoy points per night.

Bend to Portland

It takes about three and a half hours to drive nonstop from Bend to Portland via Santiam Pass, a route that starts with unmatched views of the Three Sisters mountains and cuts through Santiam State Forest before eventually joining up with Interstate 5 near Salem. But if you’re up for more hiking or waterfall viewing, there are some worthwhile stops along the way.

Sisters

About half an hour into the drive, you’ll hit the city of Sisters, a historic mountain town with an Old West feel that you’ll likely find either fun or a bit hokey. Either way, it’s worth a stop for breakfast at Sisters Coffee Company’s flagship location and roastery. The lodgelike cafe serves a variety of pastries, breakfast burritos and sandwiches, and, of course, coffee drinks. The bourbon caramel latte, made with barrel-aged bourbon syrup, is a personal favorite.

Koosah and Sahalie falls

For a short detour that packs a big punch, hop on Oregon Route 126 at Santiam Junction for nine minutes until you reach the trailhead for Koosah and Sahalie falls. This easy 2.4-mile loop trail will take you past two waterfall vistas and a deep blue McKenzie River churning with white water rapids.

If you don’t have time for the entire loop, you can go out and back as far as you’d like. Sahalie Falls is just steps from the parking lot, and you can reach Koosah Falls after about 15 minutes down the trail.

Silver Falls State Park

If you’re ready to stretch your legs again, just before hitting Salem, make your way to Silver Falls State Park. This crown jewel of Oregon’s state park system is best known for the Trail of Ten Falls, a hiking trail studded with yellow foliage during the autumn months.

The trail, which traces a canyon through the forest, is just what it sounds like: A tour of waterfalls, including the 177-foot South Falls, which you can walk behind for a unique vantage point.

Related: Giant sequoias and red rock canyons: 7 state parks with national park-worthy wonders and smaller crowds

Exploring Portland

This road trip terminates in Oregon’s largest city, Portland. Despite the urban setting, Portland doesn’t lack for outdoor opportunities. Head to Washington Park in northwest Portland to explore the Portland Japanese Garden and Hoyt Arboretum, both spectacular in the fall. If you need even more time outside, Forest Park is one of the largest urban parks in the U.S., with 80 miles of trails.

Meanwhile, nearby, the Pearl District — distinct for its converted brick warehouse architecture — is a great place to try some of the coffee and beer that Portland is famous for. On the brewery side, Backwoods Brewing Company, Deschutes Brewery and 10 Barrel Brewing Company are all within a few blocks of one another; coffee-wise, you can’t go wrong with Barista, Good Coffee (which you may remember from the Columbia River Gorge) or Stumptown, which has a nearby location in neighboring downtown. The Pearl is also home to Powell’s City of Books, the world’s largest independent bookstore.

Portland is well known for its stellar dining scene, but great food in the city doesn’t always mean fancy digs. You can eat some of the best dinners the city has to offer at casual picnic tables, as you’ll find at Montelupo Italian Market (house-made pasta) and Eem (Thai barbecue). You also can’t leave Portland without eating at a food cart pod. There are dozens across the city, but Prost! Portland has a great selection for fall, with its namesake German restaurant lending Oktoberfest vibes.

Like Bend, Portland has a lot of great day trip potential. If you didn’t get your fill of wineries in the Gorge, you can reach Oregon’s world-famous Willamette Valley wineries in under an hour. Cannon Beach on the Oregon coast — with cooler temperatures and stunning rock formations rather than swimmable beaches, plus all the nostalgia and kitsch you expect from a proper beach town — is another top destination. Whatever you do, don’t miss the views from the nearby Ecola State Park parking lot.

Where to stay in Portland

The city is home to several hotels across the Hilton, Hyatt and Marriott portfolios, giving travelers numerous options to book with points. Marriott takes the cake for luxury in the city, with The Ritz-Carlton, Portland and The Nines, a Luxury Collection Hotel, Portland taking the top two spots on the city’s list of upscale properties. Woodlark Hotel Portland, part of Marriott’s Tribute Portfolio, will appeal to design lovers and houses a beautiful coffee shop (Roseline Coffee) and a cocktail bar (Abigail Hall) on its ground floor.

On the Hilton side, The Porter Portland, Curio Collection by Hilton is a solid mid-tier option with some design flair, and Hotel Lucia recently came under the Hilton umbrella as part of Small Luxury Hotels of the World.

Meanwhile, the Hyatt Centric Downtown Portland punches above its weight with a perfect location bordering Portland’s trendy Pearl District.

When booking, consider paying cash to earn points instead of redeeming points, as many of Portland’s downtown hotels are very affordable, at under $200 a night.

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