13 Best Portland Oregon Fall Festivals

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As the autumn season begins, it’s the perfect time to explore the vibrant fall festival scene in Portland and the surrounding areas. From pumpkin patches to cider fests, there’s no shortage of fun to be had. We’ve narrowed down the top 13 must-visit harvest festivals that offer something for the whole family.

Fall leaves. Best Portland fall festivals.

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.

Chinese tea and lunch.

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 dance performances. There is also a children’s area with games and activities.

Information for the 2023 Dragon Boat Races

Dates: September 9-10

Admission: Free. Some activities may require fees.

2. Oktoberfest at Mt. Angel

Our family at Oktoberfest 2023 in Mt. Angel, Oregon. Best Portland fall festivals.

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!

Children in traditional Bavarian folk costumes dancing the May Pole dance at Mt. Angel's Oktoberfest.

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.

@dinkumtribe Mount Angel's Glockenspiel celebrates the German-Swiss- Bavarian heritage of the village and our 53 year old Oktoberfest. The first figure represents the Native Americans who came to this place to communicate with the Great Spirit, followed by figures depicting the founders of both the civil and religious communities of Mount Angel and the frivolity and fun of the Oktoberfest. ​ The Glockenspiel plays at 11 a.m., 1, 4 and 7 p.m. daily. The clock is large and clearly visible; the bells are sharp and precise in their sound. However, the animated figures are the real traffic stoppers. Wherever Glockenspiels are located, they become tourist destinations, with crowds gathering on the appointed hours to watch the figures as they dance about and listen to the resonance of the bells. (From the Chamber of commerce website). @DinkumTribe ADHD family travel @DinkumTribe ADHD family travel @DinkumTribe ADHD family travel #oregontravelideas #oregontravelguide #thingstodoinoregon #adhdfamilytravel #oktoberfest #oktoberfest2023 #mtangeloregon #mtangeloktoberfest #uniqueattractions ♬ original sound – DinkumTribe ADHD family travel

The annual Oktoberfest is held the second Thursday after Labor Day each year. The festival runs from noon to midnight each day. 

Boy in front of the Mt. Angel Oktoberfest Festhalle.

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!

Vintage cars at the Mt. Angel
Our boys LOVED the car and military vehicle show on Saturday, one of many free events that comprise Oktoberfest.

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!

@dinkumtribe If you thought that Oktoberfest was just a beer drinking festival, you’re missing the best parts! Not angels Oktoberfest is a family friendly event including dozens of performances, music, dancing, classic cars, delicious food, a free kids zone with carnival rides & a petting zoo, and SO MUCH MORE! Best of all, all of the food vendors support local nonprofit organizations, so you can eat all kinds of amazing food and know that you’re helping a good cause! @D@DinkumTribe ADHD family travel@D@DinkumTribe ADHD family travel@D@DinkumTribe ADHD family travelo#oregontravelideaso#oregontravelguidet#thingstodoinoregonm#mtangeloregonm#mtangeloktoberfesto#oktoberfesto#oktoberfest2023t#thingstodowithkidsf#familyfuntimef#fallfestival ♬ Good Time – Owl City & Carly Rae Jepsen

Of course it wouldn’t be Oktoberfest without a variety of German beers, including ales, lagers, and wheat beers. Visit the Biergarten, Hopfengarten, Englegarten, 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.

German biers.

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 dancing by local dancers, or join in the street dance yourself! 

Boys and girl in traditional Bavarian clothing dancing around flag poles.

Information for the 2023 Mt. Angel Oktoberfest

Dates: September 14-17

Admission: FREE. Biergarten and some activities may have additional fees.

3. The Cider Squeeze

Honeycrisp apple on the tree.

Head over to the Phillip 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.

Set in the beautiful surroundings of the Phillip Foster Farm in Eagle Creek, “The Cider Squeeze” 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)!

Two honeycrisp apples on tree.

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. 

Sign depicting "The Seasons for the pioneers" describing the difficulties of farming in pioneer days.

Information for the 2023 Cider Squeeze

Date: Saturday September 16, 10 am – 4 pm

Admission: $5 per individual, $20 per family

4. St. Josef’s Grapestomping Festival

Grapes on the vine.

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 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 2023 Grapestomping Festival

Dates: September 23-24 (Saturday & Sunday)

Admission (2022 info): $15 per person or $25 per couple; kids 12 and under are free.

5. Suavie Island Pumpkin Patch

Three girls in a photo cut-out depicting American Gothic at The Pumpkin Patch on Suave island.

It’s time to embrace the classic autumn traditions 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 hay rides through the fields, this patch is one of the best places to get that classic autumn experience. 

@dinkumtribe It's time to embrace the classic autumn traditions 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 hay rides 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. @DinkumTribe ADHD family travel @DinkumTribe ADHD family travel @DinkumTribe ADHD family travel #portlandoregon #fallfestival #fallfestivities #pumpkinpatch🧡 #cornmaze #portlandfall ♬ Happy and Cheerful – Hendri

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. 

Map of 2022 "The Maize" at The Pumpkin Patch on Suave Island.

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!

Gift shop with Halloween and fall themed items for sale.

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. 

@dinkumtribe 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. @DinkumTribe ADHD family travel @DinkumTribe ADHD family travel @DinkumTribe ADHD family travel #portlandoregon #fallfestival #fallfestivities #pumpkinpatch🧡 #portlandfall ♬ Halloween ・ cute horror song – PeriTune

And if you love traditional pumpkin patches like this one, check our our list of over a dozen pumpkin patches near Salem too.

Information for 2023 Suavie Island Pumpkin Patch

Dates: Daily 9 am-6 pm September-October (note that some activities have specific hours, and The Maize first opens Labor Day weekend).

Admission: Free admission and parking at the Pumpkin Patch; some activities require a fee. Check the website for specifics.

6. The Wedge (cheese festival)

Cheese and fruit platter. The Wedge is a popular Portland area fall festival.

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.

Cheese wedge and slices.

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. If you’re a fan of cheese, then you won’t want to miss The Wedge!

Information for the 2023 The Wedge Portland festival

Date: Saturday September 30 from 12-5 pm (VIP early entry at 11 am)

Admission: $25 in advance, $30 at the gate for adults. VIP entry is $65, kids 4-10 is $10.

7. Halloweentown in St. Helens

As the fall season settles in, there’s no better time to embrace the spooky spirit of Halloween. And what better way to do so than by visiting Halloweentown in St. Helens, Oregon?

Located just a short drive from Portland, Halloweentown is a must-visit destination for lovers of all things eerie and mysterious. As soon as you arrive in the town of St. Helens, you’ll notice it’s charmingly creepy atmosphere. St. Helens was the movie location for Halloweentown as well as some scenes in the Twilight movies, so be on the lookout for those photo ops.

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. 

Pumpkin carved with a giant eye. Best Portland Fall festivals.

Additionally, Halloweentown offers a variety of events and activities for visitors of all ages. Seek out Bigfoot, talk to an alien, meet with mermaids and other magical creatures, visit a haunted house, attend a pumpkin carving workshop or catch a scary movie screening. Most of the special events are on weekends, so check the calendar for the updated event schedule.

No matter what you choose to do, Halloweentown is an experience that will leave you feeling spooked and satisfied.

Information for 2023 Spirit of Halloweentown

Dates: Daily from September 16 – October 31

Admission: Visiting the town is free. Parking is limited and you should expect to pay a fee, and certain events may also require a fee. Check the website for special events schedule and other details.

8. The Portland Night Market

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 2023 Portland Night Market events

Dates: October 6 & 7, November 30-December 3

Admission: Free ($10 Fastpass allows you to skip the entry line)

9. Hood River Hops Fest

Hops growing in the Willamette Valley.

The Hood River Hops Fest is a one-day outdoor festival that celebrates the fresh hop harvest in the Columbia Gorge. The family-friendly festival features over 40 Pacific Northwest breweries, each pouring their own unique fresh-hop beers

The annual festival is held in downtown Hood River, Oregon, on the first Saturday in October. At the Hood River Hops 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!

Hops growing with red background.
Hops growing

Information for the 2023 Hood River Hops Fest

Date: Saturday, October 7

Admission: $35 for adults, $15 for designated drivers, and free for children 12 and under.

10. Portland Greek Festival

For those who are interested in exploring Portland’s cultural offerings, 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 demos 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 2023 Portland Greek Festival

Dates: October 6-8 Friday-Sunday

Admission: $5

11. The Hood River Valley Harvest Fest

Colorful vegetables and hops with blue sky in background.

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 2023 Hood River Valley Harvest Fest

Dates: October 13-15 Friday-Sunday. Hours vary by day, see event website.

Admission: Friday – $10/ person, $5 seniors and military; Saturday & Sunday – $12/ person; Weekend Pass – $20; Kids 12 and under FREE.

12. The West Coast Giant Pumpkin Regatta (Tualatin)

The West Coast Giant Pumpkin Regatta is a must-see event that takes place every fall in Tualatin, just west of 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 the Lake of the Commons. 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 2023 Pumpkin Regatta

Dates: October 21-22 (Saturday-Sunday)

Admission: Free for spectators (activities may require a fee)

13. Portland Book Festival

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 2023 Portland Book Festival

Date: Saturday November 4

Additional details TBA

So which of the Portland Fall Festivals will you choose?

Fall is the perfect time to explore the vibrant festival scene in and around Portland. 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!

©️ Copyright Jennifer D. Warren 2023.

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About the author

I’m Jenn Warren, Co-Founder and Content Creator for Dinkum Tribe. I'm a Third Culture Kid (TCK) from Jamaica and California, married to my college sweetheart. I've been a missionary kid, pastor’s kid and (former) pastor’s wife. My husband and I traveled as pastors for 12 years throughout the United States and Canada before becoming travel content creators.

I love living in Oregon and exploring new places with my family. We’ve road tripped over 30,000 miles across the United States and Western Canada with our six children since their infancy. Prior to our marriage, I also lived in Spain for a summer and spent another summer in Mexico.

I’ve homeschooled our six children for over 10 years, and served on the board of a homeschool co-op for 4 years. Several members of our family are neurodivergent (gifted, ADHD, cPTSD), and I’ve spent 5+ years learning how to accommodate neurodivergent needs as well as supporting the resultant mental health challenges (anxiety, depression).

I’ve also served as a support group leader and co-director of Pure Life Alliance, a nonprofit organization that supports families struggling with sexual addiction.

I write about family travel and road trips, millennial marriage, general parenting, homeschooling, parenting neurodivergent children, grief, and abuse recovery.

Comments

  1. You have given me some awesome ideas for what to do and see in the city during the fall. I was impressed by the variety and the quality of the festivals. The pumpkin patch, the corn maze and the Oktoberfest are some of my favorites.

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