The highest destination on the Mount Hood map is Timberline Lodge, located six curved miles up to its timberline—the altitude above which few trees grow. Here, history and winter recreation live together.

Built in 1937, the lodge has stood as a National Historic Landmark since 1977 and continues to host visitors from around the globe who come to enjoy the views from its 6,000-foot perch.

Timberline has bragging rights of operating the first chairlift in Oregon (the second in the United States), the Magic Mile which began in 1939. Since then, it has achieved two other firsts: It’s the only ski area in the United States to operate 10 months a year and it’s the only ski area with 4,540 vertical feet of skiable terrain, with its runs found at Government Camp’s Summit Pass.

Its high-alpine sister, Mt. Hood Meadows, is known for its snowfall and learning environment. With one of the largest ski schools in the Pacific Northwest, Mt. Hood Meadows offers accessible terrain on lower-lying and tree-protected runs, for all levels—beginners and powder hounds alike. Since opening in 1969, Mt. Hood Meadows boasts 87 trails, more than 2,000 skiable acres, an average snowfall of 35 feet and the area’s longest run of three miles. Down the hill, Mt. Hood Skibowl has night skiing under lights on 36 runs, making it the largest night-skiing operation in the United States with three chair lifts to access its Upper Bowl after dark.

For more advanced athletes, Palmer snowcat service runs up to three trips per day and can take 12 riders to the top of Palmer summit at 8,540 feet. Skiers and riders begin at Summit Pass of Government Camp, take a shuttle up to Timberline Lodge and then to the Magic Mile lift to meet the pickup cat at the top of Palmer. The cat ride is first come, first served.

Teacup Nordic paves the way for cross-country skiing. Volunteer-powered, the nonprofit cares for and grooms. Fifteen miles of snow track from flat and easy to challenging hills and turns. Classic and skate skiers of all ages are welcome. Founded in 1979, Teacup is just “below” Bennett Pass across from Mt. Hood Meadows Ski Area and is often skiable November through May.

Timberline Lodge is a classic ski-and-stay destination. Architecturally built with a roofline to mimic the iconic peaks and ridgelines of Oregon’s tallest mountain, the lodge pays homage to history and art, welcoming guests to ski-in or ski-out from suites to bunk-style spaces.

Down the mountain road, the incorporated communities of Mount Hood Village include Brightwood, Welches, Zigzag and Rhododendron—convenient and unique basecamps to the upper reaches of Mount Hood. For 30 years, Mt. Hood Vacation Rentals has connected homeowners to visitors in the Mount Hood corridor with cabin and cottage stays, riverfront or creekside abodes and pet-friendly places.

Cloud Cap Inn was built in 1889 near the time of the first documented mountain excursions on Mount Hood. Today, you can tour the historic Inn or visit Cooper Spur Mountain Resort, located on the mountain’s north side. Harkening to the early days of skiing, one double chair lift operates nine runs on 50 acres of beginner and intermediate terrain with 400 vertical feet. The ski area is located steps from log cabin resort accommodations, and Pacific Northwest farm-to-table meals are on the menu at Crooked Tree Tavern & Grill.

Mount Hood winter sports aren’t only about lift-served skiing. Try tubing, sledding or tobogganing. Mt. Hood Skibowl provides the tubing tracks and a conveyor belt to reach the hilltop. Reservations are required, and the sled area does sell out. Riders must be 36 inches tall.

Summit Pass offers a single-chair lift to serve a tubing hill, doubling as learning grounds for beginner and intermediate skiers and riders. Summit is the second oldest, continuously operating ski area in the United States in the heart of Government Camp.

Another mile-and-a-half higher, the Snow Bunny Sno-Park presents sledding and tubing offerings with opportunities on small or large hills. Snow Bunny is a BYOS (Bring Your Own Sled) operation that provides plenty of snow. 

An Oregon native and Portland-based writer, Kara Tatone also calls Colorado home. For more than two decades she wrote for regional newspapers and magazines while living in its small mountains towns.

A hotel in a well-located landmarked building makes an appropriate base for soaking up Philadelphia’s rich history. Loews Philadelphia sits in one of the country’s first skyscrapers, built in Art Deco style, sporting spacious rooms and a spa with a hammam. Neighboring Canopy by Hilton Philadelphia Center City has its home in the 1897 Stephen Girard building with an eclectic historic-meets-hip-hop vibe. The hotel lends complimentary bikes to guests tired of walking. For history with a twist, Guild House Hotel is an intimate boutique housed in the former headquarters of the New Century Guild, one of America’s first clubs for working women. The hotel, a National Historic Landmark, continues to honor a tradition of inclusivity while providing luxury amenities and service.