Rainy Boots, Big Vibes, Zero Regrets

Winter in Portland gets a bad rap. “Too wet.” “Too gray.” “I’ll stay inside.”

Counterpoint: winter hiking here absolutely slaps. Fewer people, louder waterfalls, moss turned up to neon, and that smug feeling of knowing you didn’t bail just because it sprinkled (okay, poured).

Grab your rain jacket—let’s go.

Why Winter Hiking in Portland Is Weirdly Awesome

• Trails go introvert-mode: Summer crowds? Gone. It’s just you, the trees, and maybe a very confident banana slug.
• Waterfalls = main character energy: Everything is flowing like it’s showing off.
• Moss everywhere: If green had a personality, this would be it.
• Cool but not cold: You’ll warm up once you’re moving—promise.

Where to Hike (When You Don’t Feel Like Freezing)

Forest Park: The “I Can Do This After Work” Hike

Rain? No problem. Forest Park’s got big trees doing umbrella duty.

• Go for: Wildwood Trail, Maple Trail Loop
• Why it rules: Close, cozy, and smells like wet earth in the best way
• Heads up: Mud happens. Embrace it. You’re outdoorsy now.

Columbia River Gorge: Waterfall Season Goes Hard

Winter is when the Gorge flexes.

• Go for: Latourell Falls, Wahclella Falls, Multnomah–Wahkeena Loop (conditions permitting)
• Why it rules: Fewer tourists, more drama (the good kind)
• Heads up: If it’s icy, don’t be a hero—turn around.

Mount Hood Foothills: Snow, But Make It Chill

You don’t need mountaineering skills to enjoy Hood in winter.

• Go for: Salmon River Trail, Trillium Lake
• Why it’s dreamy: Snow-dusted trees, peaceful vibes
• Heads up: Bring microspikes just in case—future you will be grateful.

What to Wear So You Don’t Hate It

Quick Safety Stuff

• Check the forecast and trail conditions
• Start earlier than you think (winter daylight is rude)
• Tell someone where you’re going
• Turning around = wisdom, not weakness

Final thoughts

Winter hiking in Portland isn’t about pretending it’s summer. It’s about leaning into the drizzle, laughing at the mud, and discovering that gray skies make the greens pop harder.

Put on the jacket. Go get a little soggy. You’ll come back smiling.