Portland is known for keeping it weird when it comes to so many things including food, clothing and the biking culture (think naked bike rides). But our community doesn’t stop there. Year-round, locals and visitors alike enjoy eclectic festivals and events that they would be hard pressed to find elsewhere. Beyond the well known Rose Festival, the following are festivals and events only Portlanders could dream up. Read on to find out more.

photo: Don Shall via flickr

October: West Coast Giant Pumpkin Regatta

Just around the corner,on Oct. 19th, this is one of the silliest annual thrills. Locals and visitors watch costumed competitors paddle giant pumpkins on Tualatin Lake (Like, actual pumpkins, hollowed out into actual boats. Are you with me?). The Pacific Giant Vegetable Growers supply the enormous gourds for this annual pumpkin boat race, open to paddlers over 18 chosen during a pre-event selection process. Besides cheering on the racers, there’s plenty for little ones to do, with children’s costume contests, pumpkin bowling, pie-eating contests, giant pumpkin weigh-offs, live music and great food. Don’t miss it. Click here for more details about this event.


March: Wooden Shoe Tulip Fest

Scheduled to occur in March of 2020, there’s something for the whole family at this 40-acre farm, which holds a month-long fête amidst its beds of brilliantly-colored tulips and daffodils. Along with flower and craft markets to browse, you’ll find a host of daily and weekend-only activities to delight the kids, from pony rides to zip lines. Adults can nip by the Wooden Show Vineyards tasting room for samples.

Online: woodenshoe.com

photo: via McMenamins UFO Festival

May: McMenamins Annual UFO Festival

May 14-16, just 40 miles south of Portland, the UFO Festival is scheduled to be held in Oregon’s beautiful wine country at McMenamins’ historic Hotel Oregon. Now in it’s 21st year, the festival began as a way to honor the Trent Case it and has grown to be one of the most well respected festivals of its kind.Attendees, both big and little, can expect to enjoy plenty of McMenamin’s tasty pub fare  along with lots of family fun and food for thought for true believers and skeptics alike. Click here for more info about this event.

Online: UFOfest.com

June: Festival of Flowers

The festival of Flowers, held on Jun. 7, has been one of Portland’s most renowned for over 30 years. The festival takes place in Pioneer Courthouse Square where guests are invited to meander through the landscape. The square works in collaboration with a local artist or design firm to create a floral masterpiece often totally approximately 20,000 flowers and plant materials! This year’s flower installation is expected to also include ornamental grass and Douglas fir seedlings to bring in elements of the Columbia River Gorge. There will be pathways that will allow visitors to stroll through the path of a river or traverse the Gorge itself. After the festival ends the public is invited to purchase the plant materials and flowers.

Online: thesquarepdx.org

photo: Molly Stark via flickr

June: Portland Scandinavian Midsummer Festival

Every year the Midsummer Festival is a particularly remarkable! For the first time the Portland Scandinavian Midsummer Festival has received the designation of an Oregon Heritage Tradition Day! This designation is for events that are more than 50 years old and represent what it means to be an Oregonian. Nordic Northwest dates back to 1858. There are games, food, live music, and opportunities for kids and adults to craft floral wreaths and crowns. There will also be face painting and a chance to dance around the maypole! In 2019, this summer delight was held on June 8th and will fall at a similar time in 2020!

Online: scanheritage.org/midsummer

June: Recycled Arts Festival

Who knew celebrating all things green could be so much fun? This fest is all about inspiring and encouraging families to reduce, repurpose, and recycle. Along with plenty of resources and programs, you and the kids will discover roaming entertainers, a children’s art area, and over 150 recycled art vendors. Look for this event Jun. 27 & 28 of 2020.  Click here for more details on this event.

Online: recycledartsfestival.com

photo: Dave Wild via flickr 

July: Sherwood Robin Hood Festival

In the historic and picturesque town of Sherwood, Oregon you can find one of the most unique community events in the state every summer. The annual Sherwood Robin Hood Festival attracts nearly 20,000 revelers of all ages. You can expect modern and medieval activities to fill the streets of Old Town Sherwood. The old fashioned community parade winds its way through Sherwood. Featured in the parade will be Maid Marian and her Court, Robin Hood and his Merry Men in addition to over 70 imaginative entries. Go for the dancing, entertainment, live music, interactive performances, swordplay, magicians, comedians, and so much more! There will be over 100 booths with a large variety of shopping, crafts, and unique activities. Held this past Jul. 19-20, the festival is free including the entertainment on both the Main and Family stages however please note that some vendors charge fees for various activities.

Online: robinhoodfestival.org

July: Mermaid Parade

The annual Portlandia Mermaid Parade takes place during the month of July and it is a free family friendly, gender neutral, and body positive event celebrating  water mythology and all things mermaid. You kiddos will love dressing up in sparkly, mermaid gear. ​Each year the Portlandia Mermaid Parade will choose an annual parade theme for attendees who need a little extra inspiration and want to get more involved.

Online: portlandiamermaidparade.com

August: Annual Oregon Bigfoot Festival

It should come as no surprise that locals love to celebrate our beloved resident monster. Call him Big Foot or Sasquatch, it doesn’t matter. Held this past Aug. 17, you don’t want to miss this annual party where you’ll find festival activities and lots of Big Foot look alikes running around. In it’s third year, it looks like this event is officially a favorite and will continue annually well into the future.

Online: Oregonbigfootfestival.com

photo: Ian Sane via flicker

September: Flock and Fiber Festival

Early fall is the perfect time to attend an unusual local event with cute, furry animals. For something off the well-beaten corn-maze path, head to Canby and check out this craft-centered weekend festival honoring the art of natural fibers. Visit the sheep, goats, and llamas; participate in a make-and-take workshop; and wander the marketplace to admire a wide range of handmade goods, from felted clothing to woven baskets. Kids’ activities, a cook-off, and a goat obstacle course round out the weekend. While this event was just held recently on Sept. 28 & 29, you should mark your 2020 calendars for the next one. It’s family fun that you don’t want to miss.

Online: oregonflockandfiberfestival.com

—Annette Benedetti


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