Day 1
If you can swing it, mid-week trips have quite the list of appeals. Less traffic, shorter to no lines and lower prices! Start your trip off right with breakfast and a tour of Timberline Lodge, then hit the slopes that are home to North America's longest ski season. Then break for lunch at Beer Stube at Mt. Hood Skibowl while enjoying the slope-side view and the legendary “mountain of nachos.” Spend your afternoon playing at Skibowl’s Mt. Hood Adventure Park and opt for a guided tour by one of their professional guides or show your skills off at Mt. Hood Skibowl through one of the many winter snow activities. End your day at Mt. Hood Oregon Resort in Welches, which offers amazing mid-week deals on their overnight and golf packages and pamper yourself with a head-to-toe treatment at their full-service spa. Finish the night with a delicious dinner at Altitude Restaurant.
Day 2
Head down to Sandy for breakfast at Antfarm Café & Bakery to enjoy some classic biscuits and gravy while supporting a very current farm-to-table movement. Pop across the street into the Sandy Historical Society Museum and get a quick history lesson on this all-important 175th Anniversary year of the Oregon Trail. Next stop at Jonsrud Viewpoint for some amazing views of the valley and Mt. Hood and snag a couple photos. Continue on to lunch at the Happy Valley Station Food Carts which has 18 different carts to satisfy every taste bud and indoor seating. Once satiated you’ll be ready for a round of golf at the pristine Langdon Farms Golf Club in Canby which is a favorite for all skill-levels of golfers. After the sun has set you’ll love a twinkle-lit dinner at Allium Bistro in West Linn or one of their Field & Vine Dinners in the Field events if you’re in town during one of these farm-to-table experiences.
Day 3
Make your way to the award-winning micro-roaster Happyrock Coffee in downtown Gladstone before continuing south into Oregon City for brunch classics done right at The Hive Social. Test your history buff skills at the Official End of the Oregon Trail Interpretive Center with their fully interactive exhibits showcasing pioneer life. This year is an especially good time to visit as they are commemorating the 175th anniversary of the Oregon Trail. Then hit up Main Street for a boutique shopping experience and check out the Oregon City Municipal Elevator which continues to operate as the only “vertical street” in North America. Grab lunch at Mi Famiglia Wood Oven Pizzeria for a delicious scratch made pie or delicious panini, then head over to Lake Oswego to stroll among the Gallery Without Walls outdoor sculpture exhibit.