15 Best Portland Fall Festivals and Events (Oregon) 2026

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Portland’s best fall festivals include everything from pumpkin patches and harvest celebrations to cultural festivals, Halloween events, and wonderfully unusual traditions like racing giant pumpkins across a lake.

Our family-friendly favorites include Mt. Angel Oktoberfest for all-day entertainment, the Sauvie Island Pumpkin Patch for classic fall activities, Spirit of Halloweentown for spooky fun, and the West Coast Giant Pumpkin Regatta for an unforgettable FREE family outing.

In this guide, you’ll find 15 of the best fall festivals in Portland and the surrounding areas, including Hood River, Tualatin, St. Helens, Canby, and Mt. Angel. We’ve included current dates, admission prices, event highlights, and practical details to help you choose the best festival for your family.

Whether you’re looking for cider pressing, pumpkin picking, live music, cultural food, cosplay, or a festive day trip from Portland, there’s something here for nearly every age and interest.

Portland area fall events at a glance

Event details were last verified in August 2026. Festival schedules, prices, and activities may change, so always confirm the latest information with the event organizer before you go.

This blog post provides information for general informational purposes only. While we strive for accuracy, we are not responsible for any errors or omissions, or for any actions taken based on the information provided. Readers should independently verify all event details with the official event website or organizers before making any plans or commitments.

1. Portland Dragon Boat Festival

The Portland Dragon Boat Festival is an annual event that celebrates the Chinese Dragon Boat Festival. It is held on the Willamette River in Portland, Oregon at the Tom McCall Riverfront Park. 

The dragon boat races are the main event of the festival. Teams of 20 paddlers race each other in long, narrow boats that are decorated with dragon heads and tails. The races are exciting and competitive, and they are a great way to see the Chinese culture celebrated in Portland.

In addition to the dragon boat races, the festival also features a variety of other activities. There are food vendors selling traditional Chinese food, a beer garden with local beers, and a live entertainment stage with music and lion dances. There is also a children’s area with games and activities.

Information for the 2026 Dragon Boat Races: https://portlanddragonboats.com

• Dates: September 12-13
• Time: 9 am-4:30 pm
• Location: Tom McCall Waterfront Park, Portland
• Admission: Free to watch. Some activities may require fees. There is a fee for teams to participate in the races.
• Parking: several options, all paid. See this handy graphic.

2. Rose City Comic Con – Best for fandoms

Rose City Comic Con is Portland’s premier pop culture event, offering an eclectic celebration of comics, gaming, sci-fi, cosplay, anime, and fantasy. Nearly any fandom niche you can think of will be represented, from Harry Potter, to My Hero Academia, to Marvel and DC comics, to Goonies.

What makes RCCC truly stand out is its strong focus on the creative process. The Artist Alley showcases local and independent artists, allowing attendees to interact with creators and discover new works.

In addition to celebrity guests and panels, RCCC fosters a family-friendly atmosphere, emphasizing community and artistic expression rather than massive announcements. Attendees can compete in costume contests, enjoy a dedicated Star Wars Fan Experience and participate in tabletop and video gaming.

Information for the 2026 Rose City Comic Con: https://rosecitycomiccon.com

• Dates: September 11-13
• Time: Fri 1-8 pm; Sat 10 am-7 pm; Sun 10 am-5 pm
• Location: Oregon Convention Center, Portland
• Admission: Varies based on age, purchase date, and type of experience. Anywhere from $20 (kids) to $700+ (front row seating and other perks)
• Parking: limited parking at the Convention Center and local street parking, all paid. Recommend using public transportation when possible.

3. Oktoberfest at Mt. Angel – Best all-day family fun

If you didn’t grow up in the Salem area, you might think that Oktoberfest is simply another “beer holiday”. That’s what I thought too. But Mt. Angel’s Oktoberfest is designed to be family friendly, with tons of activities, performances and lots of fun for adults and kids of all ages!

Mt Angel Oktoberfest is a four-day festival held in the town of Mt. Angel, Oregon. The festival celebrates Bavarian culture and heritage, and features traditional German food, beer, music, and dance.

We live only 10 minutes from Mt Angel, and our kids, teens and adult daughters all look forward to O’fest (as the locals call it) every year. We nearly always spend an afternoon there watching performances, eating delicious food and letting the younger kids ride the carnival rides at the Kindergarten.

The annual Oktoberfest is held the second Thursday after Labor Day each year. The festival runs from noon to midnight each day. The earliest performances start around 11 am, but some activities, like the Weiner dog run and the car show, start as early as 8 am.

Food and Drink

Mt Angel Oktoberfest features a variety of traditional German food, including bratwurst, sauerkraut, pretzels, strudel, and more. There’s even more than just traditional Bavarian foods- we saw Russian food booths, fish tacos, nachos, soft-serve ice cream, and all kinds of sweets!

Best of all, every food booth supports a local non-profit, so you can eat to your heart’s content, knowing that you’re also supporting good causes. Don’t miss the Doughboys or the dinner-plate sized Elephant ears!

Of course it wouldn’t be Oktoberfest without a variety of German beers, including ales, lagers, and wheat beers. Visit the Biergarten, Hopfengarten, Alpinegarten, Weingarten or Prostgarten and sample some new brews, both local Oregon favorites and Bavarian classics! Some of these locations require an entry fee for adults.

Mt Angel Oktoberfest is a great way to celebrate Bavarian culture and heritage. During the weekend, enjoy live music from various bands and musical ensembles throughout the day. You can also watch traditional German dance performances by local children, or join in the street dance yourself! 

Information for the 2026 Mt. Angel Oktoberfest: https://oktoberfest.org

• Dates: September 17-20
• Time: 9 am-12 am
• Location: various throughout the town of Mt. Angel
• Admission: FREE. Some venues and some activities may have additional fees.
• Parking: lots of free street parking around town. Two main parking lots for a fee. There are shuttles from Portland, Salem, Silverton and Woodburn as well if you don’t want to drive in.

Read our full post for tips on how to enjoy Oktoberfest with your kids.

4. Oaks Park Oktoberfest – Best for carnival-style fun

Oaks Park Oktoberfest, held annually at the historic Oaks Amusement Park in Portland, is one of several beloved fall events celebrating German culture in the Pacific Northwest. It’s a unique combination of authentic Bavarian festivities with amusement park family fun.

You can enjoy traditional German food like bratwurst, schnitzel, and strudel, alongside imported German beers and local craft brews.

Other family-friendly fun includes live polka music and dancing on two stages, entertaining cooking shows, and the wildly popular wiener dog races. There’s even a dedicated “Kinderplatz” that provides hands-on activities for children.

Information for the 2026 Oaks Park Oktoberfest: https://www.oakspark.com/oktoberfest

• Dates: September 25-27
• Time: TBD 2026
• Location: Oaks Park, Portland
• Admission: TBD 2026. Varies from $4.50 (for under 48″ tall, gate only) to $44.45 (for 48″ and taller, includes rides)
• Parking: Limited, available onsite for $4

5. The Cider Squeeze – Best for living history and educational experience

Head over to the Philip Foster Farm for a different type of festival experience at “The Cider Squeeze.”

This daylong event allows visitors to take part in the traditional process of pressing fresh apples into cider using an authentic cider press. The hands-on experience is enjoyable for all ages and provides a glimpse into the rich agricultural history of the Pacific Northwest.

The Philip Foster Farm is significant historically as one of the final stops on the Oregon Trail. Philip Foster and Sam Barlow built the Barlow Road, which allowed emigrants on the Oregon Trail to cross Mt. Hood into the Willamette Valley with their wagons (previously impossible).

The Philip Foster Farm hosts living history events and farm tours year-round.

“The Cider Squeeze” at Philip Foster Farm is an annual fall festival that visitors won’t want to miss.

You can bring your own apples, or buy apples at the Farm to press your own cider (up to 2 gallons per family)! Taking part in the cider pressing process will leave visitors with a sense of satisfaction in having contributed to creating something delicious and authentic.

Besides the cider press event, there’s also live music, folk dancing, kids games, blacksmithing and a variety of other historic activities to watch and participate in. 

Information for the 2026 Cider Squeeze: https://philipfosterfarm.com/farm-events/cider-squeeze/

• Date: Saturday September 19
• Time: 10 am – 4 pm
• Location: Phili Foster Farm, Estacada
• Admission: $5 per individual, $20 per family
• Parking: onsite, included with admission.

6. St. Josef’s Grapestomping Festival – Best for wine lovers

The St. Josef’s Grapestomping Festival is an annual event held at St. Josef’s Winery in Canby, Oregon. The annual celebration has been running for over 40 years and is the perfect place to celebrate the harvest season and the start of the busy crush season.

The festival features live entertainment, great food, and local wine tasting, but the main event is, of course, the grape stomping. Participants are invited to stomp on grapes in a large oak barrel, and the best stomper wins a prize. There is also a silent auction with a variety of wine-related items up for bid.

Information for the 2026 Grapestomping Festival (not available yet): https://stjosefswinery.com/st-josefs-grapestomping-2025/

• Dates: TBD 2026
• Time: TBD 2026
• Location: St Josefs Winery, Canby
• Admission: TBD 2026. $30 per couple; $100 for VIP grape stomping per couple.
• Parking: onsite, included.

7. Sauvie Island Pumpkin Patch – Best for traditional pumpkin patch fun

Embrace a classic autumn tradition at the Sauvie Island Pumpkin Patch. Located just a short drive from Portland, this pumpkin patch offers everything you could want in a fall festival.

From navigating through the corn maze to a hay ride through the fields, this patch is one of the best places to get that classic autumn experience. 

We visited The Pumpkin Patch with a high school tour last fall, and it was so much fun! We spent over an hour trying to find our way out of The Corn Maize, and that was even with the help of the navigational riddles provided. 

We also enjoyed meeting the farm animals in the barn, and exploring the well-stocked gift shop full of amazing themed Halloween and fall things. Every student and adult could find something they liked in that gift shop!

But the highlight of the visit was taking a hayride out to the field to select the perfect pumpkin to decorate or carve at home. The foggy weather gave that perfectly spooky vibe to help find our own pumpkins. 

And if you love traditional pumpkin patches like this one, check out our list of over a dozen pumpkin patches near Salem, and 9 other pumpkin patches near Vancouver Washington.

Information for 2026 Suavie Island Pumpkin Patch: https://www.thepumpkinpatch.com

• Dates: Daily September-October
• Time: 9 am-5 pm September, 9 am-6 pm October.
• Location: Sauvie Island Pumpkin Patch, near Portland.
• Admission: Free admission. Some activities require a fee.
• Parking: free onsite

8. The Wedge (cheese festival) – Best for foodies

The Wedge is a cheese festival in Portland, Oregon that celebrates all things cheese. The festival features over 60 creameries and artisan food producers, offering samples of their delicious cheeses, as well as accompaniments like crackers, fruit, and wine. 

There are also classes and demonstrations on cheesemaking, as well as a cheesemaker dinner. The Wedge is a family-friendly event, and tickets include all cheese, accompaniment, and non-alcoholic beverage samples.

The Wedge is held annually in September at Alder Block in Portland. It’s a great way to experience the world of cheese and to learn about the different types of cheeses that are available. It’s also a great opportunity to meet other cheese lovers and to share your love of cheese.

Information for the 2026 The Wedge: https://thewedgeportland.com

• Date: September 26
• Time: 12-5 pm (VIP early entry at 10 am)
• Location: Portland Night Market
• Admission: $25 in advance, $30 at the gate for adults. VIP entry is $65.
• Parking: difficult, some available for a fee. Recommend public transportation.

9. Halloweentown in St. Helens – Best Halloween fun

What better way to embrace the spooky spirit of Halloween than by visiting Halloweentown in St. Helens, Oregon? I took my teen daughter here on a weekday to scope it out, and the photo ops were next-level.

Located just a short drive from Portland, Halloweentown is a must-visit destination for lovers of all things eerie and mysterious. St. Helens was the movie location for Halloweentown as well as some scenes in the Twilight movies, and this town goes all out!

Decorations adorn the streets (including a giant lighted pumpkin at City Hall), and visitors are encouraged to dress up in their spookiest attire. Take a stroll and admire the pumpkin-lined sidewalks and spooky storefronts. 

Weekdays are the perfect time to visit if you are seeking fewer crowds and spooky vibes. We loved taking time to explore at our own pace and take all the pictures we wanted.

Additionally, Halloweentown offers a variety of events and activities for visitors of all ages, such as:

• Seek out Bigfoot
• Talk to an alien
• Meet with mermaids and other magical creatures
• Visit a haunted house
• Attend a pumpkin carving workshop
• Catch a scary movie screening

Most of the special events are on weekends, so check the calendar for the updated event schedule.

Information for 2026 Spirit of Halloweentown: https://www.spiritofhalloweentown.co

• Dates: Select days from September 26 – November 1
• Time: varies
• Location: various throughout St. Helens
• Admission: Visiting the town is free, however most attractions on weekends require a wristband.
• Parking: Limited and you should expect to pay a fee ($25 for the main lot which includes a trolley to and from the main event areas).

10. The Portland Night Market – best for shopping

Take a stroll downtown and experience the unique atmosphere of the Portland Night Market. This event showcases the creativity and talent of local artists, makers, and food vendors, making it the perfect opportunity to find one-of-a-kind souvenirs or gifts.

The market is held on select weekends throughout the fall, so be sure to check ahead of time to plan your visit.

The Portland Night Market is not just a market, but an experience. The lively atmosphere is filled with the sounds of live music and the chatter of visitors as they peruse the booths.

In addition to the unique shopping experience, the market also offers a range of food vendors serving up everything from traditional Portland cuisine to international fare. Don’t forget to try some of the delicious desserts and sweets, too!

Information for 2026 Portland Night Market events: https://www.pdxnm.com

• Dates: October 2 & 3, December 3-6
• Time: 4-11pm
• Location: Portland Night Market
• Admission: Free ($10 Fastpass allows you to skip the entry line)
• Parking: difficult, some available for a fee. Recommend public transportation.

11. Hood River Orchard and Ale Fest (formerly the Hood River Hops Fest)

The Hood River Orchard and Ale Fest is a one-day outdoor festival that celebrates the fresh hop harvest in the Columbia Gorge. It features over 40 Pacific Northwest breweries and ciders, each pouring their own unique brews. 

The annual festival is held in downtown Hood River, Oregon, on the first Saturday in October. At the Hood River Orchard and Ale Fest you can enjoy live music from local bands, eat delicious food from local vendors, shop for unique souvenirs and gifts, and enjoy the festive atmosphere with other craft beer lovers!

Information for the 2026 Hood River Orchard and Ale Fest: https://www.orchardandale.com

• Date: Saturday, October 3
• Time: 11-7 pm
• Location: Hood River Event Site, Hood River
• Admission: Free. Tasting package is $35 + fees
• Parking: onsite, may require a fee.

12. Portland Greek Festival

For those who are interested in exploring Portland’s local culture, the annual Portland Greek Festival is a must-visit fall event. This festival celebrates Greek food, music, and dance, and is held every year at the Holy Trinity Greek Orthodox Cathedral in Northeast Portland.

The festival offers family-friendly activities for all ages, whether you are interested in learning more about Greek culture, trying new foods, or simply enjoying the lively atmosphere. Be sure to check out the traditional Greek folk dancing, where you’ll see dancers of all ages and skill levels performing in colorful costumes.

While you’re there, sample some of the delicious Greek food booths, including gyros, spanakopita, and baklava. You can also participate in cooking demonstrations and learn how to make your own Greek dishes at home.

The Portland Greek Festival is an excellent way to experience a different culture and celebrate the fall season.

Information for 2026 Portland Greek Festival: https://www.portlandgreekfestival.com

• Dates: October 2-4
• Time: 10 am-10 pm Fri & Sat; 11 am-7 pm Sun
• Location: Holy Trinity Greek Orthodox Cathedral, Portland
• Admission: $5
• Parking: street parking, may require a fee.

13. The Hood River Valley Harvest Fest – Best Harvest activities

One festival that you won’t want to miss this fall is the Hood River Valley Harvest Fest. Located just a short drive from Portland down the scenic Columbia River Gorge, this festival offers a delightful mix of activities for all ages. 

From pumpkin carving and apple cider pressing to live music and local arts vendors, there’s something for everyone here. You can even take a tour of the nearby farms and orchards and enjoy the beautiful fall foliage of the Hood River Valley. 

Make sure to try some fresh produce and specialty foods, including fresh-baked pies and artisan cheeses. The Hood River Valley Harvest Fest is the perfect way to celebrate the fall harvest and all of its bountiful offerings.

Information for 2026 Hood River Valley Harvest Fest: https://www.hoodriverharvestfestival.com

• Dates: October 9-11
• Time: 1-6pm Fri; 10am-6pm Sat; 10 am-5pm Sun
• Location: Hood River Event Site, Hood River
• Admission: $10 (discount Friday for seniors and military)
• Parking: onsite, may require a fee

14. The West Coast Giant Pumpkin Regatta (Tualatin) – Most Unique Event

The West Coast Giant Pumpkin Regatta is an annual October event at the Lake of the Commons in Tualatin, Oregon, approximately 13 miles southwest of downtown Portland. This festival has become a beloved tradition in the Pacific Northwest, drawing crowds from all over the Portland area to see giant pumpkins transformed into watercraft. 

The pumpkin regatta is a sight to behold, with contestants in costume paddling their creatively carved pumpkin boats across Tualatin’s manmade lake. You can watch the races from the shore (free admission) or rent a kayak to get up close to the action. 

Beyond the race, there are many other activities to enjoy, including musical performances, face painting, and local food vendors. Don’t miss the Pacific Giant Vegetable Growers Terminator Weigh-Off (largest pumpkin) or the pumpkin bowling! Check the event website for times and parking information.

Information for the 2026 Pumpkin Regatta: https://parks.tualatinoregon.gov/events/pumpkin-regatta/

• Dates: October 18
• Time: 10 am-4 pm
• Location: Lake of the Commons, Tualatin
• Admission: Free for spectators (activities may require a fee)
• Parking: free street parking, some public lots, shuttles run from other public lots

15. Portland Book Festival – Best for book lovers

Book lovers won’t want to miss the Portland Book Festival! This festival features author discussions, book signings, writers workshops, and pop-up readings.

With over 100 authors in attendance, you’re sure to find something that piques your interest, and it even includes an extensive book fair!

The Portland Book Festival is also a great opportunity to support local writers and publishers. The festival is held in downtown Portland at the Portland Art Museum and other nearby venues and attracts thousands of attendees from all over the country.

Information for the 2026 Portland Book Festival: https://literary-arts.org/about/programs/portland-book-festival/

• Date: November 2-8
• Time: varies
• Location: various venues in Portland
• Admission: $20. Kids 17 and under free.
• Parking: limited, requires a fee. Recommend using public transportation.

So which of the Portland Fall Festivals will you choose?

These must-visit Portland fall festivals offer something for everyone, whether you’re a foodie, beer enthusiast, or just looking for a fun family weekend activity. So grab a friend, dress warm, and plan to make some great memories at the festivals this autumn!

You may also enjoy these posts:

• Best pumpkin patches near Salem, Oregon
• Best pumpkin patches in Vancouver, Washington
• Fall activities for teens and families
• Halloween activities for teens and families
• Visiting Mount Angel’s Oktoberfest with kids

©️ Copyright Jennifer D. Warren 2023-2026. Updated: August 3, 2026.

This post contains affiliate links for Amazon, Stay22 and other programs. I earn a small commission from qualifying purchases made from the links on this site, at no extra cost to you. Thanks for supporting our family business!