October brings a different energy to the Willamette Valley. Harvest is in full swing, with vineyards buzzing as grapes make their way from vine to winery and the region settles into one of its most active seasons. Cooler days, changing leaves, and the sights and sounds of harvest make this a particularly memorable time to explore wine country.

There’s plenty to experience beyond the vineyards, too. October brings harvest celebrations, wine dinners, live music, fall markets, and seasonal food and wine experiences, along with plenty of opportunities to enjoy the changing landscape. Explore the full calendar of events and start planning your visit!

Here’s your guide to October events in Willamette Valley wine country.

SEASONAL HIGHLIGHTS

As summer transitions into fall, September is a great month to linger over a meal, enjoy a special pairing, or make an afternoon of wine tasting.

• Harvest Fest & Pumpkin Patch at The Ground | Oct. 10
• Oktoberfest at Abbey Road Farm | Oct. 10 & 11
• The Great Portland Grape Stomp at Portland Wine Company | Oct. 10
• Live Pumpkin Carving at Brooks | Oct. 27
• A Killer Vintage: A Halloweek Mystery Dinner at Brooks | Oct. 28
• Halloweekend at Dobbes Family Estate | Oct. 31
• Halloween Costume Party at Brooks | Oct. 31
• Halloween Movie Night at Knudsen Vineyards | Oct. 31

GIVE BACK FOR BREAST CANCER AWARENESS MONTH

Raise a glass for a cause this October at Duck Pond Cellars! All month long, enjoy a special rosé flight featuring their new sparkling Rosé. Half of the proceeds from each flight will be donated to Breast Friends.

Dobbes Family Winery is partnering with Fighting Pretty and is hosting an event on October 10 from 12:00 – 3:00 PM to pack Strength and Beauty kits that will go directly to women in active treatment. Your $20 donation gets you a kit to pack and a complimentary glass of wine. Plus, all weekend long, enjoy a curated flight, a special Pretty Rosé on tap, and pink tumblers, with 10% of proceeds from the weekend going straight to Fighting Pretty.

FOOD & WINE EVENTS

As summer transitions into fall, September is a great month to linger over a meal, enjoy a special pairing, or make an afternoon of wine tasting.

• Ravioli Making Class & Dinner at Balsall Creek | Oct. 3
• Lucidwild + Hiyaku PDX Dinner at Lucidwild Estate | Oct. 3 & 4
• Bennies & Bubbles: Sunday Brunch at Ponzi | Weekly on Sundays
• Harvest Dinner at St. Innocent Winery | Oct. 10
• Wood-Fired Pizza Pairings at Rain Dance Vineyards | Oct. 10
• Epicurean Experience: Harvest Dinner at Archery Summit | Oct. 17
• Harvest Brunch at REX HILL | Oct. 17
• Our Vineyard Table at Ambar Estate
• Winemakers Dinner at Namaste Vineyard | Oct. 17
• Farm & Forage Dinner at big table farm | Oct. 24
• Portuguese Appetizers Cooking Class at Natalie's Estate Winery | Oct. 25
• Winemaker Dinner at Tributary Hotel | Oct. 25
• Bonfire & S'mores at Rain Dance Vineyards | Oct. 30

>>> BROWSE ALL FOOD & WINE EVENTS HERE

LIVE MUSIC & PERFORMANCES

• Weekly Live Music at Celestial Hill | Thursdays
• Friday Night Music on the Estate at J. Christopher Wines | Fridays
• Live Music Friday at Willamette Valley Vineyards - McMinnville | Fridays
• Sunday Encore at Archery Summit | Sundays
• Live Music at Chemeketa Cellars | Oct. 8 & 22
• Music in the Hills at Résonance Dundee Hills Tasting Room | Oct. 11
• Jazz in the City at Balsall Creek | Oct. 21

>>> BROWSE ALL MUSIC EVENTS HERE

MORE TO EXPLORE

• Spa After Hours at The Allison Inn & Spa | Oct. 2
  • $55 includes steam room and sauna access, s'mores, popcorn and snack bar, happy hour-priced wine and cocktails, raffle, and discounts on services and retail.
• Sips & Sights Tasting Cruise with Love & Squalor | Oct. 4
  • Two-hour cruise on the Willamette River with wine and light bites
• White Pinot Fest at Saffron Fields Vineyard | Oct. 17
  • Features 12+ wineries. Tickets are $45
• Silent Book Club at Argyle Winery | Oct. 14
  • Bring a book, grab a glass of bubbles, and find a comfy seat. No admission fee. 
• Trivia Night at Battle Creek | Oct. 21
  • Groups of 6 max, free to play, prizes, and wine – heck ya!

PEARL DISTRICT FARMERS MARKET

The Culinary Farmers' Market in Portland’s Pearl District has been extended through October! That means more complimentary wine tastings each Sunday from two different wineries, rotating each week. 

• October 4: Nysa Vineyard & Jachter Family Wines
• October 11: Dobbes Family Winery & Ricochet
• October 18: Abbey Road Farm & Furioso
• October 25: Trisaetum & Saffron Fields

📅 Every Sunday through October 25
⏰ 10:00 am–2:00 pm
📍 NW 13th Avenue between Everett & Glisan

OCTOBER IN WINE COUNTRY

Whether you’re looking to take in the changing colors, catch a glimpse of harvest, or spend a crisp fall day in wine country, there’s plenty to explore throughout the Willamette Valley.

>>> Explore all upcoming events in the Willamette Valley