One of the best ways to kick COVID Cabin fever, is by hitting the road even after the weather has turned cold. Portland’s proximity to Oregon winter adventures makes it the perfect launching pad for epic winter road trips. Pack your family’s bags and load them in the SUV. We’ve rounded up the best destinations for your crew’s Oregon family vacation. Read on for our list of best winter road trips that start in Portland.

Sisters Oregon

About three hours southeast of Portland, or half an hour north of Bend, you’ll find quaint Sisters, Oregon in the shadow of Black Butte and the Three Sisters. This winter road trip will make you feel like you're a world away with the old-fashioned storefronts and natural beauty of the surrounding area. Your family can ride horses at Black Butte Ranch or hole up with movies at a Camp Sherman cabin, or both. Sisters is also a great launching pad for ski areas like Mt. Bachelor and Hoodoo!

Driving time from Portland: 3 hours

Sisters Oregon Guide



A mere hour South of Portland, Salem has a whole new world of winter fun for kids making it an awesome winter road trip for Portland families. Stay a few days to take advantage of nearby day trips like a hike in Silver Falls State Park,. In Salem, spend some time wandering around the Oregon Garden  (Check ahead of time for COVID closures and rules). The whole family will learn a lot about state history when they tour the capitol building, and the whole family will love the the beautiful Riverfront Park on the Willamette River. 

Silver Falls State Park
20024 Silver Falls Hwy SE
Sublimity, Or


Depoe Bay

Gray whales swim to the warmer waters of Baja California in December through mid-January. Like anyone headed on vacation, they’re in bit of a hurry to get where they’re going and don’t lollygag around too much, but about 30 whales pass by whale watching sites each hour during peak times. The week of December 27th is Whale Watching Week, with multiple spots from Brookings to Astoria to help you sight these fascinating travelers. Bring your binoculars, warm clothes, and a little patience, and you might catch a glimpse. If not, there’s always storm watching, snuggling, relaxing, and tidepooling.

Driving time from Portland: 2.5 hours

Depoe Bay Whale Center
119 Hwy 101
Depoe Bay



Hey you guuuys! Head to Astoria to re-trace the steps of The Goonies. Before you head out of town, grab a copy of the movie if your kids haven’t seen it a million times already. Once you arrive, do the Truffle Shuffle at the Goonies House or re-create the “jailbreak” at the Oregon Film Museum, a great cold-weather retreat for the whole family. Once you’re done exploring outside, try one of Astoria’s family-friendly breweries like Buoy Beer, which offers up a kids’ menu along with floor-to-ceiling windows for a fantastic view.

Driving time from Portland: 2 hours

Oregon Film Museum
732 Duane St.
Astoria, Or




Timberline Lodge

Timberline Lodge is an inviting home base for a short showshoeing adventure. Rent show shoes there, or back in Portland at your favorite outdoor store. Then try out the 3/4 mile trail above the lodge for stunning views. It's not exactly easy going, so your kids should be prepared for a hike. Come back to the lodge to warm up with a heated outdoor pool, game room, and lending library.

When you're ready to go back out to brave the snow again, ask for the snowman kit ($20). A black top hat, felt scarf, carrot nose, cookie eyes, and a licorice mouth are for your snowy friend, and the thermos of hot chocolate, coffee, tea, or hot apple cider is for your crew.

Driving time from Portland: 1.5 hours

Timberline Lodge
27500 W Leg Rd.
Timberline Lodge, Or


—Annette Benedetti


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