Oregon is the perfect venue for a relaxing six-day road trip for parents and their adult children. This itinerary starts in Ashland at the Oregon Shakespeare Festival, continues to the wine country and ends in Portland.
Taste Oregon’s unique terroir in the wines produced in the little-known Umpqua Valley and in Willamette Valley, home of the state’s legendary reds. Willamette Valley lived up to promotors’ claims as a “promised land, flowing with milk and honey,” for emigrants in the 1840s seeking their fortunes as well as winemakers in the 1980s.
The author enjoyed a week in Oregon with her engaged daughter, taking a breather from wedding planning to enjoy great theater, food, wine and hotels. Read about their celebration trip in Oregon: Classy and Sassy.
Plan Your Trip. Stay two nights in Ashland, one night in McMinnville and two nights in Portland. Buy tickets to the Oregon Shakespeare Festival. The evenings are generally warm and the skies clear around Ashland, so book a performance in the outdoor theater.
Plot your route through the wine country. Willamette Valley attracts serious wine collectors. David Adelsheim is one of best-known Oregon wine pioneers and his wine has won multiple awards. “Bergström has incredibly good wine,” said Linea Gagliano with Travel Oregon. “I’ve seen grown men cry when they taste their wine, particularly the Sigrid Chardonnay.”
Book lodging close to the sights and activities you want to visit. Reserve rooms at the Ashland Springs Hotel when you buy your tickets. Reserve at the Hotel Oregon in McMinnville ahead of time. McMenamins’ historic, homey hotels are an Oregon institution and often sell out.
Fair weather is the rule, but perhaps not all day, everyday. If the weather app reports an 84 percent chance of precipitation, prepare for a downpour. The sun returns and the puddles dry up.
Learn More. Scan the Oregon Tourism website for summer attractions. This award-winning website lists suggestions for scenic, historic, natural and cultural experiences. Get a copy of Explorer’s Guide Oregon Wine Country: A Great Destination by Sherry Moore to read about the wineries with the best tasting rooms in Umpqua and Willamette valleys.
DAY 1 Portland Airport. Medford Airport. Ashland.
Fly to Ashland, Oregon.
Fly to Portland Airport (PDX) then to Medford Airport (MFR). United is the major carrier flying into Portland Airport from major North American gateways. Alaska Airlines has six daily flights to Medford.
Check into Ashland Springs Hotel two nights.
When travelers came from far and wide to the Oregon Shakespeare Festival, they stay at the Ashland Springs Hotel. Built in 1925 and carefully restored, this downtown landmark is reminiscent of small European hotels. The lobby exudes gentility and elegance. Ask for a room on the top floor for a view of the rolling hills of the Rogue River Valley.
Ashland Springs Hotel
212 East Main St., Ashland
See a Shakespeare play in the outdoor Elizabethan theatre.
The Oregon Shakespeare Festival is among America’s oldest and largest professional non-profit theaters.
It opened in 1935 with a performance of Twelfth Night. This version of the Elizabethan Theatre was built in 1959 and was patterned after London’s 1599 Fortune Theatre. Check the seating chart on the website when buying tickets. Performances run from June to mid-October.
Oregon Shakespeare Festival
Allen Elizabethan Theatre
15 S Pioneer St., Ashland
DAY 2 Ashland.
Have lunch at the hotel’s Larks Restaurant.
The team at Larks kitchen are food artists. Chef Damon Jones uses local ingredients from Oregon’s farms, orchards, dairies and wineries. The grilled Northwest steelhead, pork chop and Dungeness crab fondue are the most requested dishes. Popular desserts are the chocolate cake with salted caramel ice cream, and the cranberry-pumpkin bread pudding.
Ashland Springs Hotel
See a matinee performance in the Angus Bowmer Theatre or Thomas Theatre.
The festival grounds has two indoor theaters. The Angus Bowmer Theatre, seats 600 and is among the top four or five theaters in the nation due to its design. Stadium-type seating with a steep rake, wrapped around a fore-stage achieves an intimacy that is unusual for a 600-seat house. The Thomas Theatre seats 270 to 360, providing a flexible space. Performances run from February to November. Check the online seating charts when booking tickets.
Angus Bowmer Theatre
15 S Pioneer St., Ashland
Browse wine shops and pubs on the plaza.
Liquid Assets offers 20 wines by the glass, focusing on handcrafted wines from Oregon, California and France. At Oberon’s Three-Penny Tavern, sit back with a pint of Shakespeare Stout from Rogue Brewing Co. and enjoy the entertainment, intended for the culturally adventurous. Located upstairs on the Plaza, The Black Sheep has traditional English Bangers on the ploughman’s sausage plate, an excellent fish pie and dishes you’d expect at a British Public House.
Liquid Assets Wine Bar
96 North Main St., Ashland
45 North Main St, Ashland
Black Sheep Pub
51 North Main St, Ashland
DAY 3 Roseburg. McMinnville.
Drive to Umpqua Valley and stop at Reustle winery.
Reustle Vineyards (pronounced “rus’el”) offers an exceptional tasting experience as well as an outdoor concert space. Chickens roam the property and a paved path winds down from the raised-bed gardens through the fruit trees, to a patio overlooking the pond and vineyards. You’ll enjoy the wine and food pairings in the cave. The Estate Grüner Veltliner and Dry Riesling show the remarkable terroir of the cool, hidden Umpqua Valley.
Reustle Vineyards & Winery
960 Cal Henry Road, Roseburg
Check into McMenemin’s Hotel Oregon one night. Have dinner at Hotel Oregon’s Rooftop Bar.
Drive to historic McMinnville in the heart of Willamette Valley, a 2.5- hour drive on Interstate Hwy. 5. The handsome red brick 1905 hotel has rooms with queen- and king-size beds. Enjoy dinner on the Rooftop Bar with its unobstructed views of the Willamette wine country and distant coastal range. The entree salads are perfect on a summer evening. Try the steak and kale caesar.
310 N.E. Evans St., McMinnville
Hotel Oregon Rooftop Bar
310 NE Evans Street, McMinnville
DAY 4 Carlton. Newberg. Portland.
Visit Willamette Valley wineries.
It’s only 9 miles to Carlton, then 7 miles to Newberg. Eric Lemelson chose this farmland setting to make exceptional wines. In 1997, he built a Pinot noir production facility that uses gravity to move wine through the process. Each vineyard block is fermented separately.The Chestnut Hill Pinot Noir is a classic: aromatic with a long balanced finish. Adelsheim is one of Oregon’s founding wineries planting the first vineyard in the 1970s. The best of the estate vineyards goes into the Elizabeth Reserve. Also taste single-vineyard Ribbon Springs Pinot Noir.
12020 NE Stag Hollow Road, Carlton
16800 NE Calkins Lane, Newberg
Check into Hotel Monaco one night.
The hotel’s 221 spacious rooms could have walked off the pages of Architectural Digest. The smart, savvy, fun; eco-chic decor is instantly appealing. Our 550-square-foot suite had two queen beds with Frette bedsheets and a cozy parlour with mirrored cabinets. The hosted evening wine hour and the location, steps from the Willamette Riverfront, are also pluses.
506 SW Washington St., Portland
DAY 5 Columbia River Gorge. Portland.
Drive to Columbia River Gorge. Hike Multnomah Falls.
Hiking to the viewing platform is the best way to appreciate the 620-foot-high Multnomah Falls and the bird’s-eye view of the Columbia Gorge. The trail begins at the 1925 historic lodge. The first part of the trail takes you to Benson Bridge, the most photographed structure in Oregon.
Multnomah Falls Visitor Center
Hwy. 84, exit 31 503.695.2372
Check into The Heathman Hotel one night.
The Heathman Hotel has a dash of style that’s hard to replicate. It lives up to its star awards with programs like the Art of Sleep, a menu of mattress toppers: TempurPedic, pillow-top and feather-top. Another plus: they stock the mini-bar with Smith Tea, best in the U.S. The Lord Bergamot blend is scented with bergomot essence from Reggio Calabria, Italy. If you really want to feel like royalty, consider staying in a signature suite. The Center Stage suite has handmade costumes; the Symphony suite a cello sculpture with ginkgo-leafed branches. The Tea Court exudes civility with wood-paneling, a marble fireplace, crystal chandelier and, in the afternoon, a jazz pianist. The elegance extends to the restaurant and bar with a menu of Pacific Northwest haute cuisine.
The Heathman Hotel
1001 SW Broadway Portland, 97205
Have dinner at Veritable Quandary.
Quality ingredients, well-prepared is the core attraction at Veritable Quandary. The charming brick building is also a slice of old Portland. Book a table in the glass-walled dining room or on the patio surrounded by greenery in a park-like setting.
1220 SW 1st Ave., Portland
DAY 6 Portland. Portland Airport.
Bike to Portland’s attractions.
Stumptown and Powell’s bookstore are Portland icons. After a cappuccino, browse the shelves at the world’s largest bookstore. The Waterfront loop is the premier short bike ride in Portland, along the Willamette River, mainly on paths with a few sections on streets.
128 SW 3rd Ave., Portland
Powell’s City of Books
1005 W Burnside St., Portland
Sports & Recreation
Waterfront bike loop
Waterfront Park, Naito Parkway, Portland.
Fly or drive home.
Have the front desk arrange for a taxi or airport shuttle to Portland Airport. United, Air Canada, American, Alaska Airlines, Delta, U.S. Airways, Virgin America are the major carriers. Oregon has no sales tax so check out Pendleton, Columbia Sportswear and other stores in the terminal.
Portland International Airport
7000 NE Airport Way, Portland
—Text and photography by Donna Peck. Cover photo courtesy of Oregon Shakespeare Festival.