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Food & DrinkOctober 5A pulled pork sandwich, soup, and apple cider slushy at Sugarpine Drive-In.

The Best Fall Foods in Portland

A fall festival at Bauman's Farm apples at a Hood River orchard (Kiyokawa Family Orchards, ideally), and a Sauvie Island pumpkin patch (B...

The Weekly Wander by City Cast PortlandOctober 4A black and white goat stands elevated on a stone and wood tower outside of the Sellwood Goat House in Portland, Oregon.

Side Quest: A Smile That Can’t Be Bleat

Need a mood boost? Portland's goats deliver. Here's where to visit, feed, and hang out with the city's most charming herds, from St. John...

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The Weekly Wander by City Cast PortlandSeptember 20A pile of orange and green pumpkins at the entrance to The Pumpkin Patch on Sauvie Island. In the background, there’s a large red barn and farm store.

Side Quest: Go Big or Gourd Home

It’s almost pumpkin patch season on Sauvie Island, that time of year when caravans arrive in search of colorful squash to carve, and appl...

The Weekly Wander by City Cast PortlandSeptember 20A flock of geese descends toward the Multnomah Channel and Sauvie Island. Kayakers can be seen on the water and in the background, the Wapato Bridge rises above a floating home community.

Your Guide to Sauvie Island

Located about 10 miles northwest of downtown Portland, Sauvie Island is a slice of nature that draws city folks year-round.

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

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...

The Weekly Wander by City Cast PortlandSeptember 13Branches with green leaves frame a view of Portland’s Fremont Bridge with skyscrapers behind it.

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...

The Weekly Wander by City Cast PortlandSeptember 6Banners 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.

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...

The Weekly Wander by City Cast PortlandSeptember 6An 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.

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...

Portland's BestSeptember 1church with a purple blue sky and birds in the air above a domed church with swifts

What To Do in Portland in September 2026

September brings migrating swifts, Comic Con, Geek Week, and the start of apple-picking season, with plenty of ways to enjoy Portland’s f...

Portland Life HacksSeptember 1People in lawn chairs and on grass in front of a stage with the sign “Jazz Festival” visible.

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.

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

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...