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Annual Events and Festivals in Portland
Published on: May 12, 2020
Close up shot of man in kilt with striped socks and cleats holding a heavy ball on a chain for the Highland Games for article Annual Events and Festivals in Portland for newcomers moving to Portland.

There’s always something happening in Portland from concerts, movies, and holiday gatherings.   Events take place everywhere in the city.  From “Portland’s living room,” (Pioneer Square) to the waterfront, there is something for everyone.  For example, the over 100-year-old annual tradition of The Portland Rose Festival, or Portland Guadalajara Sister City Association’s Cinco De Mayo.  Of course, there is the sultry summer sounds of the four-day Waterfront Blues Festival.  The Portland Relocation Guide has gathered the annual events and festivals in Portland for you!

Food, Extreme Activities, and MORE!

If you’re a foodie, there are Wine, Beer, Chocolate, and Seafood festivals.  In addition, there are farmer’s markets with the regions best offered.  However, if you’re into more outrageous activities, there are those slightly out-of-the-ordinary happenings like the World Naked Bike Ride, The Big Float, the Highland Games, and the PDX Adult Soapbox Derby.

Love music? Experience some of the country’s best music as world-class musicians and their fans gather together at events.  These events include the Portland Jazz Festival and the Pickathon Indie Roots Music Festival.  Of course, music lovers take in the Music Fest NW.   This event is held at multiple venues over two days and showcases headliners with emerging local acts.

Peruse the wares of local artisans at Portland’s Saturday Market the nation’s longest-running open-air arts and crafts bazaar.  Or, take in the women of the Rose City Rollers throw elbows as they skate their way to roller derby victory.  Furthermore, if you love flowers, take a walk through acres of brightly colored tulips at the Wooden Shoe Tulip Festival.  Additionally,  there are many small local venues hosting dancing, karaoke, classes, live music, trivia nights, and much more.  You’ll find that in Portland there truly is something to fit everyone, all year long. For a full search of Portland area events, check out Travel Portland’s updated calendar at calendar.travelportland.com.

JANUARY

Oregon Chocolate Fest

Love chocolate? You won’t want to miss Oregon Chocolate Fest a weekend dedicated to sampling and savoring everything from artisan truffles to drinking chocolate from more than 80 exhibitors at the Oregon Convention Center.

Rose City Rollers Roller Derby

Portland’s all-female flat-track roller derby league, the Rose City Rollers, holds local and national bouts at the historic Oaks Park rink in Southeast Portland from January to June.

Fertile Ground Festival

Founded in 2009, the Fertile Ground Festival is focused on new Portland art. The 10-day, citywide festival showcases play premieres, art installations, events, and even in-progress projects, all created by local artists.

Chamber Music Northwest Winter Festival

Known for its popular summer series, Chamber Music Northwest also presents a suite of concerts in late January/early February.  www.cmnw.org

FEBRUARY

Portland International Film Festival

Held by the Northwest Film Center, the Portland International Film Festival is the granddaddy of Portland’s 20-plus annual film festivals, filling two weeks with 100 local premieres from around the globe.

Portland Jazz Festival

Celebrating both the jazz genre and Black History Month, the Portland Jazz Festival is packed with more than 150 concerts, including performances by major international artists and scores of free gigs showcasing local talent.

Chinese New Year at Lan Su Chinese Garden

The two-week Chinese New Year celebration, held in late January and early February at Lan Su Chinese Garden, includes lion dances, children’s activities, martial arts, and cultural and historical demonstrations. The festivities culminate with a traditional lantern-viewing ceremony.

Oregon Seafood and Wine Festival

Scheduled smack dab in the middle of the Dungeness crab season, this upscale festival celebrates both the bounty harvested from the Pacific Ocean and the state’s vineyards. More than 130,000 square feet (3,962 square meters) at the Oregon Convention Center.  However, time allows plenty of room for Oregon Seafood and Wine Festival-goers to wander while enjoying great food, wine, and live music.

MARCH

Portland Ticket to Dine

Top eateries offer four weeks of delicious deals during Portland Ticket to Dine (Formerly Portland Dining Month). In fact, in 2015, more than 100 restaurants participated, each presenting three-course menus.

Portland Saturday Market

The nation’s longest-running open-air arts and crafts market, the Portland Saturday Market features artisans selling their wares in a scenic riverside setting — open on Sundays, too. www.portlandsaturdaymarket.com

Timbers MLS Soccer

Catch a Portland Timbers game at downtown Providence Park or at a nearby Timbers bar and meet the fiercely loyal fans of the Timbers Army. The Timbers’ season runs from March until October. www.portlandtimbers.com

POW Fest

The annual Portland Oregon Women’s (POW) Film Festival focuses on the art and cinematic contribution of women filmmakers from around the world. Spanning four days, the roster of events comprises an exhibition of films made by women, moderated filmmaker panels, and filmmaker workshops. www.powfest.com

St. Patrick’s Day

It’s no surprise that always-green Portland has plenty of St. Paddy’s Day festivities. Led by Kells Irish, the annual St. Patrick’s Festival includes plenty of live music, amateur boxing, Irish dance performances and plenty more inside the large pub and special festival tent outside. You might also catch locals and visitors — around 35,000 of them — taking to the street for the Shamrock Run, the second-largest running and walking event on the West Coast and a Portland tradition since 1979.

APRIL

Wooden Shoe Tulip Festival

The month-long Wooden Shoe Tulip Festival showcases more than 40 acres of tulips and daffodils in bloom at the Wooden Shoe Tulip Farm in Woodburn, 45 minutes south of downtown Portland. Weekend events include food, wine, pony rides for the kids, and, of course, tulip viewing. www.woodenshoe.com/tulip-fest

Faux Film Festival

Every year, on the weekend closest to April Fools’ Day, Portland’s Faux Film Festival highlights the finest in fake film. That means three days of side-splitting counterfeit commercials, phony movie trailers, mockumentaries, and all forms of satire and spoofs at the historic Hollywood Theatre. www.peripheralproduce.com

MAY

Portland Farmers Market

Most of the area’s farmers’ markets open in May. Among the items featured are fresh produce, flowers, seafood, bread and berries. There are three Portland Farmers Markets in downtown Portland: Saturdays, in the South Park Blocks at Portland State University; Mondays, at Pioneer Courthouse Square; and Wednesdays, in the South Park Blocks at Salmon Street. In addition to shopping, the markets feature chef demonstrations and other entertainment. www.portlandfarmersmarket.org

Cinco de Mayo Fiesta

The Cinco de Mayo Fiesta, Portland’s largest Latino event, offers authentic Mexican music, crafts, and entertainment in Waterfront Park, including performers from Guadalajara, one of Portland’s sister cities. www.cincodemayo.org

Bridgetown Comedy Festival

The popular Bridgetown Comedy Festival draws top comics like Reggie Watts and Janeane Garofalo and was voted the nation’s best comedy festival in the 2010 Punchline Magazine readers’ poll. Spanning a weekend, the fest includes shows at multiple Southeast Portland venues, including Doug Fir Lounge.

Crafty Wonderland Super Colossal Sale

This biannual sale from the popular purveyor of local crafts, Crafty Wonderland, turns the Oregon Convention Center into a true wonderland of all things handmade each spring and winter. The May event is scheduled so you can find the perfect made-in-Portland gifts in time for Mother’s Day. www.craftywonderland.com

Memorial Weekend in Wine Country

During Memorial Weekend in Wine Country, more than 150 Willamette Valley wineries, many not usually open to the public. open their doors to visitors. www.willamettewines.com

Portland Rose Festival

Since 1907, the Portland Rose Festival has been the city’s quintessential event. The family-friendly fest kicks off Memorial Day weekend and includes the Grand Floral Parade, dragon boat races, concerts, and more.  www.rosefestival.org

JUNE

Portland Rose Festival

The Portland Rose Festival, which celebrated its centennial in 2007, offers three weeks of family events, spanning late May and early June. Highlights include the Rose Festival Grand Floral Parade, the Starlight Parade, a family carnival in Waterfront Park, dragon boat races, concerts, and fireworks. www.rosefestival.org

World Naked Bike Ride

Portland’s version of the World Naked Bike Ride is the largest one in the world. In fact, in 2014, 10,000 cyclists took to the streets in this free, clothing-optional nighttime trek through the city. www.pdxwnbr.org

Oregon Zoo Summer Concerts

Every summer, fans of folk, rock, world music, and more stake out spots on the amphitheater lawn at the Oregon Zoo for the Oregon Zoo Summer Concerts.  Featuring more than a dozen performances from some of the hottest, most diverse acts performing today. www.oregonzoo.org/Concerts

Portland Pride

Portland Pride is the city’s annual lesbian, gay, bisexual, and transgendered (LGBT) community celebration.  The event features a parade, live entertainment, and family events at Waterfront Park. www.pridenw.org

Chamber Music Northwest

Pre-concert picnics on the lawn at Reed College are a standing tradition among the enthusiastic followers of the annual Chamber Music Northwest concert series.  The event runs from late June to late July. Since it was launched in 1971, the festival has grown into one of the most successful chamber music events in the nation.  www.cmnw.org

Lake Oswego Festival of the Arts

Twenty minutes from downtown Portland, the Lake Oswego Festival of the Arts features art demonstrations, an art show, and a juried craft show with 120 booths, wine, beer, food, and entertainment. www.lakewood-center.org

JULY

Waterfront Blues Festival

The Waterfront Blues Festival is the largest blues festival west of the Mississippi River.  The festival rocks crowds on the riverbank in Waterfront Park and on the water itself with five days of top national acts, as well as spectacular fireworks on July 4. www.waterfrontbluesfest.com

Chamber Music Northwest

Pre-concert picnics on the lawn at Reed College are a standing tradition among the enthusiastic followers of the annual Chamber Music Northwest concert series.  The series runs from late June to late July. Since it was launched in 1971, the festival has grown into one of the most successful chamber music events in the nation. www.cmnw.org

Oregon Brewers Festival

Craft breweries from around the United States bring more than 80 beers to the Oregon Brewers Festival.  Notably the largest gathering of independent brewers in North America, the festival is held in downtown Portland’s Waterfront Park. www.oregonbrewfest.com

Cathedral Park Jazz Festival

Founded in 1981, the three-day Cathedral Park Jazz Festival is now the West’s largest and oldest free celebration of jazz and blues. Held in Cathedral Park beneath the historic St. Johns Bridge, the scenery is almost enough to steal the show.

PDX Pop Now!

The PDX Pop Now! festival highlights as many as 50 local independent artists at a single venue over the course of two days. The volunteer-driven nonprofit behind the festival also produces an annual compilation CD of local music. www.pdxpopnow.com

The Big Float

Every summer, The Big Float celebrates the river that runs through the city with a flotilla of inner tubes and inflatable toys and a beach party just south of the Hawthorne Bridge in downtown Waterfront Park. www.thebigfloat.com

Portland Highland Games

This celebration of all things Scottish features dancing, piping, drumming and fiddling, traditional food, and the “heavy events”.   Events include the caber toss and the Portland stone, a 96-pound rock hurled by only the brawniest athletes. The Portland Highland Games are held just east of Portland in Gresham. www.phga.org

Portland Zine Symposium

Portland’s DIY culture is alive and well, and you can catch it in all its vibrant blacks and whites at this annual gathering of underground media connoisseurs. The Portland Zine Symposium is a free, two-day event that includes workshops, panel discussions, and tables of people buying, selling, and trading zines. www.portlandzinesymposium.org

Noon Tunes

Since 2002, Pioneer Courthouse Square has celebrated summer with two free lunchtime concerts every week in July and August. The popular Noon Tunes Concert Series showcases the best in regional and local musical talent each Tuesday and Thursday from noon-1 p.m. www.thesquarepdx.org/events

AUGUST

Pickathon

Since 1999, the Pickathon Indie Roots Music Festival, a celebrated six-stage folk festival at the lush Pendarvis Farm just outside Portland, has attracted headliners like Feist and Andrew Bird while establishing itself as the nation’s greenest music festival. www.pickathon.com

MusicfestNW

Established in 2001 to showcase local musicians and bring in national acts, MusicfestNW features two days of concerts on two stages in downtown Waterfront Park. www.musicfestnw.com

PDX Adult Soapbox Derby

Fearless grown-ups hurtle down an extinct volcano in homemade vehicles during the PDX Soapbox Derby. It could be a recipe for disaster, but, instead, it’s a beloved annual event held in Mt. Tabor Park. Spectators bring their own beer and cheer on the fastest and kookiest gravity-powered cars. www.soapboxracer.com

Bridge Pedal

The Providence Bridge Pedal is an annual bike ride across Portland’s bridges that cements Portland’s bike-friendly status, as a total of 10 bridges partially close to cars, affording bicyclists rare views and a choice of relaxed rides ranging in distance from 14 to 36 miles (23-58 km).

Hood to Coast Relay

The Hood to Coast is the world’s largest running relay race, stretching 200 miles from the top of Mount Hood to the Pacific Ocean in Seaside. The overnight event culminates in the West Coast’s largest beach party and draws more than 12,000 runners and walkers annually. The race fills up months in advance, but there’s no charge to watch the dedicated and costumed runners make their way down the mountain and onto the beach. www.hoodtocoast.com

Art in the Pearl

More than 100 artists offer up their creations, from painting and photography to jewelry and hand-crafted furniture, for Art in the Pearl over Labor Day Weekend in the North Park Blocks, with food vendors, musicians, and family activities rounding out the offerings. www.artinthepearl.com

SEPTEMBER

Time-Based Art (TBA) Festival

During the Time-Based Art Festival, presented by the Portland Institute for Contemporary Art (PICA), visual artists, musicians, dancers, and other creatives from all over the world push boundaries with installations, performances, and interactive art experiences. www.pica.org/tba

Art in the Pearl

More than 100 artists offer up their creations, from painting and photography to jewelry and hand-crafted furniture, for Art in the Pearl over Labor Day Weekend in the North Park Blocks, with food vendors, musicians, and family activities rounding out the offerings. www.artinthepearl.com

Portland Film Festival

Portland has its fair share of film festivals, but the Portland Film Festival is one not to miss. The weeklong celebration of film that MovieMaker magazine called “one of the coolest film festivals in the world” is jam-packed with networking, workshops, guest speakers, film premieres, financing talks, director Q&As, and more. www.portlandfilmfestival.com

OCTOBER

Portland Trail Blazers Basketball

Winners of the 1977 NBA Championship, the Portland Trail Blazers play at the Moda Center; Blazers faithful take in games from October to April at the nearby Spirit of ’77 and other Blazers sports bars. www.trailblazers.com

Portland Fashion Week

Portland Fashion Week, the world’s only comprehensively sustainable fashion week, features independent, eco-couture, street and active wear offerings from North American and international designers, all at downtown Pioneer Courthouse Square. www.portlandfashionweek.net

The Corn Maize on Sauvie Island

Just 25 minutes north of downtown Portland, The Pumpkin Patch celebrates the harvest and Halloween with two giant corn mazes: one “haunted,” and one sporting a different locally themed design each year. www.portlandmaze.com

Haunted Houses

Portland likes its scares as much as any other city and has the haunted houses to prove it. Some of the biggest annual options include Fright Town at Memorial Coliseum. www.frighttown.com

The Spirit of Halloweentown

Thirty miles (40 km) north of Portland, the town of St. Helens celebrates The Spirit of Halloweentown all month long with giant scarecrows, a haunted house and 10 nights of spooky ghost tours.

Portland Open Studios

The artist’s life is a lonely existence, save for Portland Open Studios: two weekends in October when visitors are invited into the studios to watch, learn, and — the creators hope — buy. Through the purchase of the Open Studios Tour Guide, guests (two per guide) can get up close with sculptors, painters, printers, and more and explore Portland’s participating art spaces. www.portlandopenstudios.com

Portland Queer Film Festival

The annual Portland Queer Film Festival showcases feature, documentary, and short films offering a glimpse into the lives of lesbian, gay, bisexual, and transgender people and communities in different parts of the world. The festival attracts thousands of filmgoers during its 10-day run at Northwest Portland’s Cinema 21.

Portland Marathon

The Portland Marathon, founded in 1972, is consistently ranked as a top national race. Named “Most Walker-Friendly Marathon” by Runner’s World magazine, it attracts tens of thousands of spectators and draws participants from around the world. In true Portland fashion, the route had tons of live entertainment; in the past, that meant rock, jazz, and country bands, street performers, a mandolin orchestra, a jug band, two 18-piece big bands, aerobic dancers, high school cheerleading squads, and more. www.portlandmarathon.org

Hood River Valley Harvest Fest

The counterpoint to April’s Hood River Valley Blossom Festival, this is your chance to catch the tail end of the fruit-growing process at the Hood River Valley Harvest Fest. The fruit is picked and it’s time to party with music, food, wine, and a quilt raffle. One hour and fifteen minutes from downtown Portland.

West Coast Giant Pumpkin Regatta

Watch giant pumpkins race across the lake at Tualatin Commons, 25 minutes southwest of Portland, as boaters navigate these oversized gourds toward the finish line of the West Coast Giant Pumpkin Regatta. This free, wacky, and entertaining event is the only one of its kind on the West Coast.

NOVEMBER

Portland Book Festival (Formerly Wordstock)

After nine years, Portland’s premiere literary festival experienced a renaissance. Now a one-day event, Portland Book Festival is the largest celebration of literature and literacy in the Pacific Northwest. It includes an extensive book fair, large-scale events, smaller panels, on-stage conversations and readings, all held at the Portland Art Museum.

Portland VegFest

Founded in 2005, VegFest features speakers, cooking demonstrations, and samples galore at the Oregon Convention Center — all highlighting the health, environmental, and taste benefits of a plant-based diet. www.portlandvegfest.org

Holiday Tree Lighting

On the day after Thanksgiving, thousands of people gather in downtown’s Pioneer Courthouse Square to see the ceremonial lighting of the spectacular 75-foot-tall tree and celebrate the official start of the holiday season. www.thesquarepdx.org

Wine Country Thanksgiving

During Wine Country Thanksgiving, more than 160 wineries and tasting rooms in the Willamette Valley open their doors for special tastings and holiday festivities.  Held over Thanksgiving weekend (Friday-Sunday), this event offers the opportunity to visit some of the region’s small, family-owned wineries that aren’t usually open to the public.    In addition, meet winemakers, enjoy specialty food pairings and live music, all while savoring the region’s acclaimed wines. www.willamettewines.com

ZooLights

It wouldn’t be the holidays in Portland without a visit to the Oregon Zoo’s annual winter festival ZooLights. As you walk around the zoo, you’ll see a dazzling display of a million and half lights, and experience your zoo in a whole new light. ZooLights runs from late November to just after the New Year. www.oregonzoo.org/visit/zoolights

DECEMBER

Christmas light displays

Some of Portland’s bright spots include ZooLights, a display of more than a million lights at the Oregon Zoo, an awesome display at The Grotto, and the Christmas Ship Parade.  Moreover, the event features brilliantly decorated boats on the Willamette and Columbia rivers. www.oregonzoo.orgwww.christmasships.org,

Crafty Wonderland Super Colossal Holiday Sale

This biannual sale from Crafty Wonderland, a downtown haven of locally made goods, turns the Oregon Convention Center into a true wonderland of all things handmade each spring and winter. The December event is scheduled so you can find the perfect made-in-Portland gifts in time for the holidays. www.craftywonderland.com

 

For a full search of Portland area events, please visit Travel Portland’s website at calendar.travelportland.com.