City Cast Portland logo

Best Rainy Day Hikes Near Portland

Posted on November 7, 2023   |   Updated on September 30, 2025
City Cast Portland staff

City Cast Portland staff

path through mossy wet branches

Take a walk in the rain. (Norther Emily)

Get yourself some waterproof socks — yes, that’s a real thing, apparently — and get outside in this weather.

Here’s the list of the best hikes for the rainy season, from Norther Emily of Wild Solitude Guiding.

Solo Hikes, Possibly Earbuds In

Speaking of introversion, it’s a good time of year to hike alone. “It's kind of nice and meditative to put your hood up and enjoy the sounds of the rain,” says Emily. “It's not a good time to hike with a friend and try and have a conversation because your jacket's gonna be too loud.”

Where do you go with earbuds in, when you’re a little distracted? “I would steer clear of anything that doesn't have a lot of space for passing and includes mountain bikes.”

These are hikes that are even better with musical or podcast accompaniment:

Waterfalls

Some waterfalls dry up in summer; some get smaller. But now’s the time to see them in full force. “There's just a ton more water moving through,” says Emily. “Any of the waterfall hikes in the Gorge would be really excellent this time of year, and you're also going to deal with less crowds.”

Waterfall Alley:

A Coast Range option:

River Rambles

“Rambles” are a leisurely sort of hike, without a bunch of elevation gain. The first especially is family-friendly, says Emily.

Foggy Hikes

Sometimes, it’s about the journey, not the destination. “It’s pretty fun to be in a cloud,” says Emily. “It’s nice to be in this bubble in the trees.”

These hikes offer a payoff even if there’s not a view:

What should you do if you get soaked? Norther Emily offers health precautions and other rainy-weather hiking advice on a recent City Cast Portland podcast.

When It’s Time to Jog

Share article

Hey Portland

Stay connected to City Cast Portland and get ready to join the local conversation.

Can't subscribe? Turn off your ad blocker and try again.

Portland's Best

See All

The latest in Portland

The Weekly Wander by City Cast PortlandSeptember 13

Side Quest: Charting History’s Course

While most of the Overlook neighborhood sits above the bluffs, the industrial area of Swan Island down below does actually fall within it...

An aerial photo from 1935 shows the Swan Island airstrip, built on a peninsula that juts out into Portland’s Willamette River.
The Weekly Wander by City Cast PortlandSeptember 13

Your Guide to Overlook

Beyond the views, the North Portland neighborhood has plenty of perks: access to the MAX Yellow Line, cocktail lounges, and residents who...

Branches with green leaves frame a view of Portland’s Fremont Bridge with skyscrapers behind it.
The Weekly Wander by City Cast PortlandSeptember 6

Side Quest: Pre-Game Routine

We don’t want to throw you off your game, but we do have some fun suggestions to spice up your traditions on the way to the Rose Quarter...

Banners and window art on the Moda Center show Portland Trail Blazers figures and history. In front of the arena, a person rides a bike by a sign that spells out Rip City.
The Weekly Wander by City Cast PortlandSeptember 6

Your Guide to the Lloyd District

For 66 years, the Lloyd Center was a place where Portlanders made memories, went shopping and ice skating, and even put in the miles mall...

An aerial shot shows the roof and twin glass spires of the Oregon Convention Center, with high-rise office buildings of the Lloyd District in the background.
Portland Life HacksSeptember 1

Tips for a Better September 2026 in Portland

September is still summer in Portland, with outdoor events, farmers markets, and a major traffic disruption to plan around.

People in lawn chairs and on grass in front of a stage with the sign “Jazz Festival” visible.
The Weekly Wander by City Cast PortlandAugust 30

Your Guide to the Pearl District

Portland’s largest outdoor art fair is celebrating its 30th anniversary Saturday, Sept. 5 through Monday, Sept. 7 under the trees in the...

People browse artist booths under the trees at Art in the Pearl. In the foreground, colorful glass sculptures sit on pedestals.
The Weekly Wander by City Cast PortlandAugust 30

Side Quest: Art in the Heart

Born from Portland’s creative warehouse scene, the Pearl District remains an arts hub, with galleries, museums, public art, and vibrant c...

A colorful abstract painting of a person hangs on a wall to the left. In the background, two figures observe different paintings at the Froelick Gallery in Portland, Oregon.
Portland, ExplainedAugust 27

How Well Do You Know Our Local Mascots?

Portland Fire, the city’s WNBA team, revealed their new mascot this week after much fanfare.

Pink dragon in a Fire jersey.