The 6 Most Anticipated Fall Activities in Portland

As the air turns crisper and the colors warmer, fall’s arrival signals a magical season in Portland that beckons us outdoors. The promise of cozy sweaters, the subtle scent of fallen leaves, and the anticipation of pumpkin-spiced everything – it’s a time of year that stirs excitement in the hearts of all. So, without further ado, let’s dive headfirst into the cornucopia of fall activities that Portland has laid out for us.

#1 Have Fun at the West Coast Giant Pumpkin Regatta

When: October 22, 2023, 10:00 AM to 4:00 PM

Where: 8325 SW Nyberg St, Tualatin, OR 97062

Admission: free

Since 2004, the West Coast Giant Pumpkin Regatta, one of the state’s most unique fall festivals, is truly a spectacle that has been charming the crowds. This quirky event attracts folks from all corners of the country to witness an affair like no other: costumed characters paddling inside giant pumpkins in a series of races.

However, the fun doesn’t stop there as this action-packed event includes entertainment, foods that will satisfy your fall cravings, and activities like pumpkin golf, pumpkin bowling, and much more. The Pumpkin and Pints (on Saturday, Oct. 21) and the 5K Regatta Run/Walk (on Sunday, Oct. 22) are the additional events during the Regatta weekend.

Be sure to mark your calendars and witness giant pumpkins, supplied by the Pacific Giant Vegetable Growers, in action. It’s a day of pure pumpkin fun!

#2 Prost! To the Oaks Park Oktoberfest! 

When: September 22-24, 2023

Where: 7805 SE Oaks Park Way, Portland, OR 97202

Admission (Gate Only): $7 for 48” & taller; $4 for under 48” tall

Admission (Gate + Rides): $43.95 for 48” & taller; $22.95 for under 48” tall

Oaks Park Oktoberfest is more than just a celebration of beer; it’s a festivity of delicious cuisine, music, dancing, family fun, and a whole lot more. This festival is a must-visit for anyone looking to savor a day or a weekend of Oktoberfest in Portland.

Now let’s talk about the real stars of the show: the food and the beer. Quench your thirst and hunger with authentic German favorites featuring imported beers served alongside locally crafted wine and cider. Some of the entertainment during this event includes The Polkatones, Leikarringen of Portland, The Tirolean Dancers, and Red Shoe Rocktoberfest.

Additionally, there’s a chicken dance contest, buddy bar challenge, pretzel toss contest, cooking shows, wiener dog races, and more. With Oaks Park’s rides and attractions, you’ll get to experience a genuine Oktoberfest with a thrilling adventure. From the new AtmosFEAR to kiddie rides, everyone will surely find something fun on the midway.

#3 Enjoy the Pumpkin Patch and Hayrides at Sauvie Island’s The Pumpkin Patch

When: September 24 – October 31, 2023

Where: 16511 NW Gillihan Rd, Portland, OR 97231

Admission: free

Celebrate Halloween and the bountiful joys of October at The Pumpkin Patch on Sauvie Island. The family farm prides itself on growing 55 different crops annually, offering fresh produce, and practicing sustainable agriculture. This event promises a fun-filled, wholesome experience for the entire family.

Beyond pumpkins, there are numerous activities to indulge in. Enjoy the free pumpkin-picking hayrides and visit their iconic 1929 The Animal Barn. Apart from that, there are also paid activities like the Cow Train ($5/person) and The Maize which cost $8 for ages 13 and up, $6 for ages 6-12, and 5 and under are free. You can buy souvenirs, home decor, hats, and more at The Pumpkin Cottage Gift Shop and The Produce Market.

In October, Sauvie Island features Beer & Hard Cider on tap as well as other fall treats like Apple Cider Mini Donuts and The Pumpkin Patch – Pumpkin Spice at The Patio Cafe. Several specialty food booths like caramel apples, kettle corn, pronto pups, and pulled pork are also available.

#4 Go on a Halloween Boo Cruise 

When: October 28, 2023

Where: 1010 SW Naito Pkwy, Portland, OR 97204

Admission: starts at $50

Set sail on the spookiest cruise of the season with Portland Spirit’s Boo Cruise. This 2.5-hour affair offers a hauntingly good time, perfect for those aged 21 and older who are ready to costume up, dance, and bask in the spirit of the night.

As the moonlight dances on the Willamette River, the city’s top DJs will keep the tunes coming to ensure that the dance floor is alive with eerie energy. The cruise also features a tantalizing bistro menu and two full-service bars. Don’t forget to bring your A-game costume because prizes await for the most captivating and creative costumes.

Dress to impress in your Halloween best, and make sure to bring your ID—it’s required for this one-of-a-kind experience aboard the Portland Spirit.

#5 Celebrate Cheese at The Wedge

When: September 30, 2023, 12:00 PM to 5:00 PM

Where: 100 SE Alder St, Portland, OR 97214

Admission: $25; $75 (VIP)

The Wedge, a fromage fanatics’ paradise, is a farmers market-style festival where you can indulge in all things cheesy and delicious. It’s a family-friendly event that welcomes cheese lovers of all ages which makes it the perfect outing for everyone.

At this celebration, you can not only sample numerous local artisan cheeses but also take some home with you. And it’s not just about cheese; you can explore a variety of specialty foods, along with cider, beer, and wine, all designed to complement your cheese experience.

Tickets grant access to an array of cheese samples as well as non-alcoholic beverages and accompaniment. You’ll have to pay an additional $15 to sample adult beverages which will include a commemorative glass. Plus, every ticket comes with a $5 voucher to purchase your favorite or new cheese discovery.

#6 Indulge in Sweet Fall Delights

As fall sweeps across Portland, savor a delectable lineup of seasonal treats. The Pumpkin Spice Pecan Old-Fashioned at Blue Star Donuts is a cozy symphony of pumpkin spice, pumpkin purée, and a generous sprinkle of brown buttered-kissed salted pecan. On the other hand, Mikiko Mochi Donuts’ Caramel Apple Pie (filled) has fresh apple pie filling with koji caramel and gluten-free crumble topping.

For a taste of fall in a scoop, head to Salt and Straw Ice Cream for the Pumpkin Spiced Tiramisu, a harmonious blend of spiced coffee ice cream, maple syrup, cinnamon, clove, and ginger swirled with tiramisu cake and drizzled with chocolate stracciatella and coffee mascarpone. Grab a can of Portland Cider’s Pumpkin Spice Cider for a crisp breeze with a spicy aroma of pumpkin pie (without the pumpkin), accented with all the fresh flavors of the season.

Black Rock Coffee Bar’s Pumpkin Blondie is also a must-try which is a twist on their all-time favorite drink, The Caramel Blondie. It’s made with hints of pumpkin, caramel, and white chocolate then topped with nutmeg + cinnamon. With each treat bursting with seasonal flavors and autumnal bliss, embracing the fall spirit with these delights truly captures the essence of the season.

Now, it’s your turn to share your excitement. What’s your most anticipated fall activity or event in Portland? Drop a comment below, and let’s come together to revel in the beauty and joy of this bewitching season!

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