City Cast Portland logo

Side Quest: From Beyond the Grape

Posted on October 11
Ben McBee

Ben McBee

Fog sits low among the fields and trees of Willamette Valley wine country. In the foreground, green grape plants show signs of fall as leaves begin to turn yellow.

Willamette Valley wineries are putting the terror in terroir this Halloween. (Photo courtesy of Willamette Valley Wineries Association / Benton-Lane Winery)

Eerie mist hovers over unending rows. Hordes gather and slowly make their way out of the suburbs. Figures bring cups of red liquid to their lips. It’s harvest time in Willamette Valley wine country — and that chill in the air just ran down your spine, didn’t it?

Sure, pumpkin patches are a great way to get into the spooky season, but so is wine tasting — and many of the local vineyards host hair-raising (and glass-raising) happenings in October. Check them out, if you dare.

🍷 What’s more unnerving than a pour you weren’t prepared for? That’s the energy at Saffron Fields Vineyard’s White Pinot Fest (Saturday, Oct. 17), a showcase of producers who take Oregon’s signature grape and turn it into something unrecognizable.

🎃 Highlights of Brooks Wine’s Halloweek festivities include a live pumpkin carving demonstration where you can chat with local artist Joey Edwards (Tuesday, Oct. 27), as well as “A Killer Vintage,” an interactive mystery dinner where guests work together to crack the case (Wednesday, Oct. 28).

🎥 Take in “The Rocky Horror Picture Show” on the big screen at Knudsen Vineyards’ Halloween Movie Night (Saturday, Oct. 31), where costumes are encouraged, and each ticket comes with a bag of Miss Hannah’s Gourmet Popcorn.

see more:things to do

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.

The Weekly Wander by City Cast Portland

See All
The Weekly Wander by City Cast PortlandOctober 11

Your Guide to Tualatin

Don’t rock the gourd or you’ll miss Tualatin’s West Coast Giant Pumpkin Regatta when it returns Oct. 18. Join the fun and see what else t...

Two costumed people — one dressed as an aviator and the other in a squirrel suit — paddle their giant pumpkins toward the finish line at the West Coast Giant Pumpkin Regatta in Tualatin. Crowds of people cheer them on in the background.
The Weekly Wander by City Cast PortlandOctober 4

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...

A black and white goat stands elevated on a stone and wood tower outside of the Sellwood Goat House in Portland, Oregon.
The Weekly Wander by City Cast PortlandSeptember 20

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...

A 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.
The Weekly Wander by City Cast PortlandSeptember 20

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.

A 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.
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.

The latest in Portland

Food & DrinkOctober 5

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...

A pulled pork sandwich, soup, and apple cider slushy at Sugarpine Drive-In.
Neighborhood GuidesOctober 4

Your Guide to Parkrose

Petting zoo, line dancing, and live music: Portland Fall Fest hits Rossi Farms on Oct. 4. Here’s how to make a day of it in Parkrose, plu...

A mural at 10721 NE Sandy Blvd. in Portland’s Parkrose neighborhood depicts farmers working in fields colored orange, red, and green. The blue-hued figures load yellow crates onto a blue truck.
Portland Life HacksOctober 2

Tips for a Better October 2026 in Portland

You know what’s coming: The next six months in Portland involve a lot of rain and colder weather, so let's get ready for it.

River with the steal bridge in the background, I-5 on the right side, downtown showing on right
Portland's BestOctober 1

What To Do in Portland in October 2026

Check out these classic October outings in Portland, including corn mazes, fall foliage viewing, and Halloween celebrations.

Tree leaves turning red.
Neighborhood GuidesSeptember 27

Your Guide to Kerns

When members of the Holy Trinity Greek Orthodox Cathedral moved into the large church at the corner of Northeast Glisan Street and 32nd A...

A street view from the corner of Northeast Glisan Street and Northeast 28th Avenue of the Apambichao Building, a cream and white colored Victorian apartment building that sits above Pambiche, a Cuban restaurant painted a deep blue.
Food & DrinkSeptember 27

Take a Tour of Franz Bakery in Portland

There are some things you knead to dough (sorry, seasonal allergies are the worst) about Franz Bakery, a fifth-generation, family-owned b...

Loaves of Franz bread tumble off of a conveyor belt at Franz Bakery in Portland, Oregon.
Portland's BestSeptember 1

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...

church with a purple blue sky and birds in the air above a domed church with swifts
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.