Oregon's Best Road Trip for Eco-Lovers

Crater_Lake_OregonCrater Lake, in the Cascade Range
Asterixvs / Dreamstime.com

Crater Lake, in the Cascade Range

A land of towering firs, crystal-clear lakes, and farmers markets, southern Oregon has long been ahead of the eco-friendly curve.

When my boyfriend, Alex, and I want to escape New York, we head north to the Catskill Mountains—we love the free-spiritedness of the towns, the artists' retreats hidden in the woods, and the tiny restaurants and cafés serving fresh foods from local farms. So when we started planning a trip out west, I had a feeling we'd flip for Oregon, a place that has practically perfected this way of life.

Friends who used to live in the state recommended that we start in Bend—if you want to immerse yourself in Oregon's crunchiness, they said, this outdoorsy city in the central part of the state is the place to be. After a three-hour drive southeast from Portland over the snowcapped Cascade Range, we get our first taste of Bend's character at theDeschutes Brewery, where nearly every item on the menu is organic. The burgers? Made with locally raised, hormone- and antibiotic-free elk and beef. The buns? Baked with the brewery's leftover grain. Even the mustard is homemade.

After lunch, Alex and I wander over to the WednesdayFarmers Market, set up on a hillside next to the Deschutes River. The stalls are filled with the most beautiful array of seasonal produce—radishes, snap peas, mushrooms of every stripe (maitake, lion's beard, shiitake)—as well as grass-fed elk short ribs and buffalo patties, and artisanal cheeses. We buy a carton of strawberries and sit on the grass to listen to a folk singer and watch a trio of toddlers take turns somersaulting down the hill. I read that Bend has become a center for young families—transplants from cities like Portland and Seattle—and I can see why: If I were a kid, there's nothing I'd rather do than roll around in the grass here on a sunny afternoon.

The town has a quirky side, too, and it's on full display at our hotel,McMenamins Old St. Francis School. The 1930s Catholic schoolhouse was converted into an inn in 2004, and the 19 guest rooms, each named after a former priest, teacher, student, or town character, are decorated with old class photos. In the hallway, a varsity football jersey and pine lockers line the walls. A woman with a cluster of star tattoos on her upper arm and a name tag that reads FREE STAR checks us in and gives us a map of the property. Next to the inn is a movie theater (built in the old parish hall), a restaurant and bar, and a Turkish bath. Alex and I grab our bathing suits and make a beeline for the blue-tiled pool to take a soak beneath the open-air ceiling.

McMenamins Old St. Francis School
700 NW Bond St., Bend, 877/661-4228, mcmenamins.com, from $114

Deschutes Brewery & Public House
1044 Bond St., Bend, 541/382-9242, deschutesbrewery.com, elk burger $12

Bend Farmers Market
Mirror Pond in Drake Park, Bend, 541/408-4998, bendfarmersmarket.us, Wed. 3 p.m.–7 p.m., June to mid-Oct.

In the morning, Free Star callsCrater Lake National Park to check road conditions in the southern Cascades, where we're heading. "Nobody's picking up," she says. "You should probably assume that the northern entrance isn't open yet." The lake, which sits at the top of a 12,000-foot-tall dormant volcano, gets an average of 533 inches of snow each year; apparently, the snow up there doesn't start melting until mid-June.

With North Entrance Road closed, we'll have to loop around to the park's southern entrance, which adds an extra 50 miles to the trip. As we drive south from Bend, we catch glimpses of purple mountains through the deep-green blur of the Douglas firs along the road. Then we start to climb in elevation, and the temperature drops from 70 degrees to the mid-30s in the span of just 20 minutes. Snow is packed five feet high on the sides of the road. We round the last bend before the summit, and Crater Lake comes into view. I don't think I've ever seen colors so dazzling in my life. The lake isn't just blue—it's a saturated, magnificent blue, the kind that looks doctored in photos. The surface is so still that it perfectly reflects the brilliant white snow and green pine trees on the peaks around it; it's as if nature created the world's largest mirror.

I wanted to stay at the 71-room Crater Lake Lodge, which sits right on the water's edge, but it was already booked up when I called in mid-spring. Instead, I reserved a cabin at theUnion Creek Resortin Rogue River National Forest, about 20 miles to the southwest, resigning myself to the fact that it probably wouldn't match the drama of staying atop the mountain. When we arrive at the 1930s lodge, though, I'm pleasantly surprised: The 23 cabins are spread out beneath 100-foot-tall Douglas firs, and ours has a private fire pit out front. The interior of our cabin, on the other hand—faux-wood-paneled walls, chintzy carpeting, and a polyester blanket on the bed—leaves us a little cold.

There's only one place to eat this far into the forest: a restaurant dating from the 1920s calledBeckie's, directly across the road from our cabin. Beckie's is down-home all the way, with pine-wood walls, antique cast-iron bar stools, and, according to the menu, a former owner named Cecil who had a glass eye and was "quite the lady." Dinner—chicken-fried steak for Alex, pork chops for me—is tasty, but the huckleberry pie steals the show. The crust has a made-from-scratch flakiness, and the berries, plucked from bushes on the slopes of the Cascades, pop with flavor.

Union Creek Resort
56484 Hwy. 62, Prospect, 541/560-3565, unioncreekoregon.com, from $48

Beckie's Cafe
56484 Hwy. 62, Prospect, 541/560-3563, unioncreekoregon.com/beckies.htm, pork chops $12

Crater Lake National Park
Off Hwy. 62, Crater Lake, 541/594-3000 (road conditions), nps.gov/crla, $10 per car

As we head out of the foggy mountains and into the more arid Rogue Valley, we make a detour to Jacksonville for a cup of coffee. We love the town so much that our pit stop turns into a half-day excursion. Jacksonville is a modern take on an Old West town: The façades of the 1850s brick buildings are still intact, but the spaces behind them have been transformed into modern establishments such as a sleek sushi restaurant that doubles as a jazz bar.

AtGoodBean Coffee Company, an organic-coffee roaster in an 1850s billiard hall, we strike up a conversation with the barista, Michelle. When she moved here 10 years ago, she says, the town was recovering from its long post-Gold Rush downturn. Then a second wave of Californians came in—this time young professionals, artists, and restaurateurs. "But the small-town vibe hasn't gone away," she says. "I know how half the people here drink their coffee."

We buy a pound of Dark Mountain blend—one of 16 varieties the shop roasts—and stroll down the main drag, California Street, looking for a place to get lunch. We scan the menu in the window atMacLevin's Whole Foods Deliand are taken aback: It's a Jewish deli, in a former tin shop. "We have to eat here, if only for the randomness of it," I say. The place is a two-person operation: Owners Jeff and Penelope Levin—who fell in love with Jacksonville when they visited from California in the late 1990s—cook and work the front of the house, respectively. Alex opts for the open-faced whitefish sandwich and a potato latke, while I order matzo ball soup and a tuna salad sandwich.

We jump back in the car after lunch and drive about 15 minutes east to Ashland. The town is home to theOregon Shakespeare Festival, which takes place every year from February to November, and life here positively revolves around the Bard. Elizabethan flags hang from the lampposts, and Shakespeare's face is on everything, from the walls of hotels to restaurant menus. The effect is a little kitschy, typical of a tourist town. But I'm hopeful; if more than 100,000 people flock here every year, the performances must be worth it.

Our first order of business is to go to the box office to pick up our tickets forOthello, one of three plays being performed at different theaters tonight. (I ordered the tickets three months in advance; in the summer, it's tough to buy them at the door.) Then we check in at our hotel, theMorical House Garden Inn, a restored 1880s farmhouse set amid a two-acre garden of lilies, jasmine, lavender, and peonies. The owner, Alicia Hwang, relocated to Ashland in 1999 from Beijing, where she had taught English for five years, and eventually bought the inn. Hwang has filled the place with art she's collected over the years: antique sculptures from Japan and Taiwan, brass works by a Canadian artist, vases by a local ceramist. (Thankfully, there's not a Shakespeare head in sight.)

Tickets in hand, we rush up the hill just before dusk for the show. We choseOthellomore for the stage than the play itself—it's at the open-air Elizabethan Stage, which is modeled after London's 16th-century Fortune Theatre, complete with a three-story façade of a half-timbered Elizabethan home as a backdrop. Right before the show, a crew member opens a window on the top story and raises a flag up a pole—the way the beginning of every play was announced in Shakespeare's time. The cast does a fine job, particularly the actor playing Othello, but the real highlight of the show is watching the sun set slowly over the Cascades as the actors recite their lines in the twilight.

Morical House Garden Inn
668 N. Main St., Ashland, 541/482-2254, moricalhouse.com, from $96

GoodBean Coffee Company
165 S. Oregon St., Jacksonville, 800/480-4036, goodbean.com

MacLevin's Whole Foods Deli
150 W. California St., Jacksonville, 541/899-1251, whitefish sandwich $12, closed Tues. and Wed.

Oregon Shakespeare Festival
15 S. Pioneer St. (box office), Ashland, 541/482-4331, osfashland.org, tickets from $20

Eugene has Ken Kesey to thank for its ultraliberal spirit: The LSD-loving author grew up and died here and, though he spent a good chunk of his adulthood in California, he had a huge influence on the town. His legacy persists today—the city leans so far to the left, in fact, that it's sometimes referred to as the People's Republic of Eugene. When Alex and I get to theSaturday Market after the three-hour drive from Ashland, it makes the market in Bend look tame in comparison. There are hippies, all right—women wearing crowns made of tinsel and ribbon, and old men with beads in their gray beards. On a grassy patch in the shade, a band plays bluegrass music on guitars, banjos, washboards, and a kazoo. Across the street at the farmers market, vendors sell bouquets of flowers, bushels of mesclun, and orange beets.

We grab a bite to eat from an Afghan food vendor and sit on a wall next to some bongo players. All of a sudden, a wiry older man with his silver hair tied back and wearing a tie-dyed T-shirt and denim vest starts dancing alone in the square. Everyone cheers and claps—and I find myself smiling. I'd join in, too, if I had the proper attire.

Saturday Market
Eighth Ave. and Oak St., Eugene, 541/686-8885, eugenesaturdaymarket.org, open Apr. to mid-Nov.

Flying into Portland is the best option from most parts of the country; reaching Bend or Eugene by air usually requires at least one stop (two if you're coming from the East Coast). For the quickest—and most scenic—route to Bend from Portland, head southeast on Route 26 over the Cascade Range. The drive should take about two and a half hours.

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