As you know, I’m an avid all-weather hiker—not afraid to get wet or muddy—and I love finding the perfect trails that keep me moving despite the forecast. Winter in the Pacific Northwest isn’t something to hide from—it’s something to embrace. Moss glows brighter, waterfalls roar louder, and fewer people mean more quiet time. Cooler temps mean less sweat and no bugs!

If you’re craving fresh air, movement, and a little winter pick-me-up, these are some of the best winter hikes near Portland that stay accessible, scenic, and magical during the colder months.

1. Lower Macleay to Pittock Mansion

Distance: ~5 miles round trip
Location: Forest Park

This is a regular for a reason—and it’s especially beautiful in winter. Starting at Lower Macleay Park, the trail winds along Balch Creek, through ferny forest, passes the stone Witch’s Castle, and climbs toward Pittock Mansion for sweeping views of Portland (and sometimes Mt. Hood on a clear day).

Why it’s great in winter:

• Well‑maintained and accessible year‑round
• Magical mossy forest scenery
• Perfect after‑rain atmosphere

2. Multnomah Falls to Wahkeena Falls Loop

Distance: ~5 miles loop
Location: Columbia River Gorge

This stunning loop links two of the Gorge’s most famous waterfalls. Start at Multnomah Falls and wind past towering cliffs and lush forest before descending alongside Wahkeena Falls. Stop at Wahkeena Springs for a serene pause. For fewer crowds and free parking, consider starting at Wahkeena Falls and hiking up to Multnomah.

Why it’s great in winter:

• Waterfalls are powerful and dramatic
• Fewer crowds than summer months
• A classic Oregon experience with moody winter beauty

3. Tryon Creek State Natural Area

Distance: Multiple loop options
Location: Southwest Portland

Lucky me—I can walk to Tryon Creek right from my doorstep! This little patch of forest feels like a hidden gem tucked into the city. Gentle boardwalks, soft elevation changes, and towering old-growth trees make it a peaceful winter escape—especially after a light rain. Weekends can get busy, but if you go on a weekday afternoon, you might have the trails all to yourself!

Why it’s great in winter:

• Lower elevation = usually snow‑free
• Ideal for mindful walks or casual hikes
• Dog‑friendly trails

4. Herman Creek Trail

Distance: ~5 miles round trip
Location: Columbia River Gorge

Herman Creek Trail is a scenic winter hike that winds through lush forests and follows the sparkling Herman Creek. With gentle elevation and peaceful forest vibes, it’s a perfect trail for anyone getting back into hiking and finding their hiking legs this winter. You will need a Northwest Forest Pass to park in the lot (available on-site).

Why it’s great in winter:

• Quiet and less crowded than summer months
• Gorgeous forest scenery
• Ideal for a relaxed winter adventure

5. Silver Falls State Park (Trail of Ten Falls)

Distance: Up to 7.5 miles loop (shorter options available)
Location: ~1.5 hours from Portland

If you’re up for a day trip, Silver Falls in winter is next‑level. Waterfalls thunder, crowds thin out, and the forest feels alive. Due to December rains, some of this trail may still be closed, so check before heading out. It’s worth the drive! We like to stop for lunch in Silverton after the hike. An Oregon State Parks annual pass or day pass is required to park (available at the kiosk).

Why it’s great in winter:

• Iconic Oregon scenery
• Multiple route options depending on conditions
• Cooler temps make longer hikes more comfortable

Winter Hiking Tips for Portland‑Area Trails

“There is no such thing as bad weather, just bad clothing.”

Before you head out, keep these winter hiking essentials in mind:

• Wear waterproof shoes and layers
• Check weather and trail conditions
• Bring traction (microspikes or crampons and hiking poles) if heading toward higher elevations
• Start earlier—shorter daylight hours matter

And always let someone know where you’re going.

Embrace the Season

Getting outside in the winter isn’t optional for me—it’s a necessity. No matter the weather or trail conditions, I always come back feeling inspired, reset, and showing up better for my family and clients as a result. I know it can be tough if you’re more of a fair-weather hiker, but trust me—you won’t regret taking the plunge. We’re so lucky to be surrounded by this kind of beauty year-round; sometimes it’s just about shifting our perspective on what a winter hike can be.

If you’re craving more Pacific Northwest adventures, local gems, and lifestyle inspiration, be sure to subscribe to my YouTube channel  or follow me on Instagram!  

With love and presence,
Pam
Licensed in Oregon & Washington

503-347-8551 | yogabugrealestate.com