This fall my wife and I took three weeks to drive from New York to Oregon. Upon arriving on the West Coast we decided to celebrate the completion of our transcontinental trek. But how to do it without breaking the bank? The solution was to spend our first night in Portland at the Kennedy School, an old elementary school that had been converted into a hotel, complete with a restaurant, brewery, bars, and even a movie theater. Its eccentric decor appealed to my artist wife and the tab ($94 a night) appealed to my frugal nature.

The Kennedy School is one of seven hotels in the quirky McMenamins chain, which includes more than 40 pubs and microbreweries in Oregon and Washington. (There are 14 McMenamins pubs in the Portland area alone.) The Brothers McMenamin, Mike and Brian, have been wildly successful at transforming old, sometimes improbable properties into popular eateries, taverns, and hotels. They do it with a combination of respect for each place’s history and a sense of humor, using a skilled and creative group of architects, artists, decorators, and historians for the renovations.

Under the McMenamins’ stewardship, a former poor farm, a shuttered Catholic school, and an immigrant meetinghouse in a warehouse district have all been remodeled into hotels or resorts.

The Kennedy School was named after J.D. Kennedy, a local builder who donated the land on which it was built. It opened its doors as a public school in 1915 and closed in 1980. It reopened in 1997 as a McMenamins hotel and brewery.

We stayed in the Math Room, one of 35 guest rooms in the school. Others are named after teachers or students. All the rooms still have the original blackboards and coat closets. The walls of our room were decorated with math equations. The ceilings were high and the windows were huge, providing a feeling of spaciousness and abundant light in the morning. Our one complaint was that our private bathroom lacked a tub.

The night we stayed at the Kennedy School we could have caught a film in the auditorium turned-movie theater. There’s no charge for guests, but it costs $3 if you’re not staying at the school. Films that have recently left first run theaters are screened and patrons are allowed to bring pizza and beer into the theater (only those 21 and over are admitted). A few times a year the Kennedy School hosts radio performances by the Willamette Radio Workshop, a Portland-area group. It happened that we were there on Halloween night, when the radio drama group performed “Frankenstein.”

That evening we opted instead to catch Portland’s premier old-timey ensemble, the Foghorn String Band, playing at a bar across town; the band also plays at the Kennedy School once a month as part of the free Thursday-night music series. Foghorn is accompanied by the veteran square-dance caller Bill Martin.

Drinking is now allowed at the Kennedy School. The smoke-free Honors Bar has classical music playing, while jazz is the soundtrack in the Detention Bar, where customers are not only permitted to smoke but can purchase an array of fine cigars.

We ordered McMenamins Terminator Stout (a rich, semisweet ale) and Hammerhead Ale (a copper-colored, medium-bodied brew) with our dinner at the school’s Courtyard Restaurant, a cavernous eatery housed in the old school cafeteria. Parked in a booth with a view of a fire roaring in a huge blue ceramic fireplace outdoors, we had a delicious meal of beef stew ($9.65) and salmon ($11). The following morning we ordered a tofu scramble and a smoked salmon scramble, both quite savory (each guest gets an $8 breakfast voucher).

Before heading off, we wandered around the Kennedy School halls admiring the eclectic decor. We saw a mural in the auditorium that depicted, among other aspects of the school’s history, Gus the Duck, who had apparently been a “neighborhood character.” In a nine-page brochure on the building’s art we learned that Gus intimidated dogs and followed children to school in the mid-1940s.

The Kennedy School, 5736 N.E. 33rd Ave., Portland, Ore., 888-249-3983,www.kennedyschool.com;$84 a night Sunday through Thursday; $94 a night Friday and Saturday.

Other McMenamins Hotels

EDGEFIELD, 2126 S.W. Halsey, Troutdale, Ore., 800-669-8610, www.mcmenamins.com; rooms $40 to $175.

Once the Multnomah County Poor Farm, this 38-acre spread in the town of Troutdale is about 15 miles east of Portland. The area is considered the gateway to the Columbia River Gorge, which has a series of waterfalls and parks for hiking. Edgefield has a winery, and reproductions of the poor-farm rules grace the walls of the resort.

OLD ST. FRANCIS SCHOOL, 720 N.W. Bond St., Bend, Ore., 877-661-4228, www.mcmenamins.com; rooms $94 to $125; hostel $30 a person a night.

The newest of the McMenamins hotels (it opened in November) was once a Catholic school in Bend, Ore., but now it offers rooms in the main building plus four cottages that sleep from two to 10 people, as well as a hostel with bunk beds. Bend is located in the high desert country in the middle of the state, where recreational opportunities, include skiing and rock climbing, abound.

OLYMPIC CLUB HOTEL, 112 N. Tower Ave., Centralia, Wash., 866-736-5164, www.mcmenamins.com; rooms $40 to $65; packages for two including lodging, dinner, beer and breakfast, $65 to $75.

This historic hotel originally opened in 1908 and was remodeled in 1913. Located halfway between Portland and Seattle in the town of Centralia, Wash., it has the usual McMenamins amenities (brewery, movie theater, restaurant, and bar) plus a billiard parlor. Every room commemorates a “significant character” from the place’s past, including Roy Gardner, the notorious train robber captured at the hotel in 1921. A train package with a two-for-one companion ticket is available on Amtrak’s Cascade Line.

HOTEL OREGON, 310 N.E. Evans St., McMinnville, Ore., 888-472-8427, www.mcmenamins.com; rooms $50 to $110.

An old four-story hotel in close proximity to Oregon’s wine country. Some 80 wineries in the Yamhill Valley are within striking distance and tours are organized by the hotel’s staff. A rooftop bar offers views of the lush wine country and coastal mountain range.

GRAND LODGE, 3505 Pacific Ave., Forest Grove, Ore., 877-992-9533, www.mcmenamins.com; rooms $40 to $185.

This former Masonic Lodge in Forest Grove, Ore., (west of Portland) has 77 rooms, multiple restaurants, and some small bars. The beaches of the Pacific are a little more than an hour away. Also nearby: a sake factory and 11 wineries.

THE WHITE EAGLE ROCK ‘N’ ROLL HOTEL, 836 N. Russel St., Portland, Ore., 866-271-3377, www.mcmenamins.com; rooms $30 to $50.

Housed in a building that was once a meetinghouse for Polish immigrants, this McMenamins has only 11 rooms. The hotel is situated in North Portland’s burgeoning industrial district and affords guests the opportunity to stay near the Portland Convention Center for trade shows and the Rose Garden, where the Portland Trailblazers play. The saloon on the ground floor has live bands most nights, and as one McMenamins staffer noted, “It can go pretty late there.”