The Best Festivals & Fairs in Portland & Oregon

by Paul Joseph  |  Published January 21, 2020

The coastal US state of Oregon is renowned for its natural beauty, characterised by abundant forests, dramatic mountains, and idyllic beaches. Its largest city, Portland, is one of the state’s biggest attractions thanks to its offer of great outdoor living combined with a rich cultural and entertainment scene, most notably in its contributions to the worlds of art, theatre and music.

Hot air balloons at the Wooden Shoe Tulip Festival just east of Woodburn, Oregon. (Photo: Kirt Edblom via Flickr / CC BY-SA 2.0)

There are a vast number of festivals and fairs that take place across Oregon throughout the year, many of which are hosted in the city of Portland. If you’re planning a trip to Oregon in 2020 and would like to find out about some of the events being held during your stay, we’ve created a comprehensive list of the best festivals and fairs coming to Oregon and Portland throughout this year.

Fertile Ground Festival

Every entertainment show has to start somewhere and in Portland that ‘somewhere’ could very likely be the Fertile Ground Festival. Now in its 11th year, the festival is organised by the Portland Area Theatre Alliance and sees the city’s live venues filled with new works of theatre, dance and comedy shows. The event is a major community occasion that gives local writers and performers the chance to showcase their talents in front of script-chasers, workshop-watchers and culture vultures. Indeed, testament to the festival’s influence is the fact that since the inaugural festival in 2009, more than 70 Fertile Ground-originated works have gone on to further productions, locally, nationally, and at festivals worldwide.

LOCATION Venues across Portland DATES 30 January 2020 

A reenactment of the suffragette movement at the Fertile Ground Festival (Photo: Fertile Ground via Flickr / CC BY-SA 2.0)

Portland Seafood & Wine Festival

Like all of America’s coastal states, Oregon serves up world class seafood – and its wine isn’t too shabby either. If you like either, or both, of these gastronomic categories then this hugely popular festival is certain to please. Featuring over 200 food and drink exhibitors showcasing the region’s very best seafood and wines, the event attracts visitors from far and wide. There’s also plenty of kids entertainment, with face painting, balloon artists, and more.

LOCATION Oregon Convention Center, Portland DATES 31 January–1 February 2020 

Portland Winter Light Festival

Each year the Portland Winter Light Festival revolves around a particular theme and for 2020 it’s “Into the Dreamscape”. Once again the festival will offer up more than 100 gifted media artists who will be putting on eye-catching displays and shows, including video projection mapping, fire sculpture and live performances across the city. There’s also live ice sculpture carving, audio-video installations, and artist talks to enjoy.

LOCATION Venues across Portland DATES 6-8 February 2020 

Oregon Truffle Festival

A marriage of world-class wines and reputable truffles makes the Willamette Valley an acclaimed region for dedicated gastronomes the world over. Each winter, which is peak season for Oregon truffles, the Oregon Truffle Festival honours its fruitful soil with two weekends of celebrations in January & February, with visitors invited to seek out and sample the four distinct varieties of native Oregon truffles. The February event takes place in the Yamhill Valley, situated at the heart of Oregon wine country, and tickets for several enticing à la carte events are still available for 2020.

LOCATION Yamhill Valley & Surrounding Areas DATES 14-16 February 2020

Delicate hands prepare truffles at the Oregon Truffle Festival (Photo: Kathryn Elsesser)

Oregon Chocolate Festival

Humans have been infatuated with chocolate for thousands of years and visitors to Oregon in early March have the chance to worship at the temple of the sacred cocoa bean at this acclaimed chocolate festival. Regional chocolatiers, artisan food producers and other taste makers participate in a wide range of chocolate-themes events, including workshops, talks, chef demos, panel discussions, a dessert competition, and plenty more. Away from the heart of the action, there’s also a Friday evening Chocolate Maker’s Wine Dinner, a Chocolate Sunday Brunch, and then 5k & 10k runs to help burn off those calories and bring your delightful indulgence to a happy end.

LOCATION Ashland Hills Hotel & Suites, Ashland DATES 6-8 March 2020

A chocolate dish is raised in front of crowds at the Oregon Chocolate Festival (Photo: Neuman Hotel Group)

Portland International Film Festival

For more than 40 years, the Portland International Film Festival has provided an acclaimed showcase for new world cinema. Over two full weeks, through the exhibition of nearly 150 feature films and short films, movie lovers descend on the city’s theatres and cinema houses to watch the very latest works by some of the world’s leading established and emerging filmmakers. There are also parties, visiting artists and other events.

LOCATION Northwest Film Center’s Whitsell Auditorium, Portland DATES 6-15 March 2020 

Savor Cannon Beach Wine & Culinary Festival

Thanks in large part to its warm climate, Oregon boasts a world class wine producing heritage and each year this festival offers visitors the chance to immerse themselves in the region’s vibrant wine scene. Local businesses all take part in the festival by hosting wine tastings and culinary events, and there’s also a Saturday Wine Walk that invites guests to sample wines from 40 Northwest wineries as they enjoy a whistlestop tour of local art galleries, shops, restaurants and hotels.

LOCATION Tolovana Inn, Cannon Beach DATES 13 March 2020 

Nourished Festival

The Nourished Festival, a gluten-free food fest, is visiting Portland for the first time this April at the Oregon Convention Center. The festival brings together over 100 brands exhibiting the best gluten-free and allergen-friendly products all in one room. Attendees can sample gluten-free food and drinks, try new products before buying them in the store, attend free presentations, and take home a reusable bag full of goodies. All products at the show are gluten-free, but many are also nut-free, paleo, keto & plant-based.

LOCATION Oregon Convention Center, Portland DATES 18-19 April 2020 

A Nourished Festival stall-holder cooking up a treat (Photo: The Nourished Group)

Crafty Wonderland

If you’re visiting Portland and are looking for a great souvenir or gift to take away with you, then Crafty Wonderland is the perfect place to be. They have two brick and mortar stores open year-round that exclusively carry work by Portland artists (808 SW 10th Ave. and 2022 NE Alberta St.). Plus, twice a year they host the city’s largest arts & craft market featuring more than 250 vendors showcasing their creative wares. The styles on display range from modern to kitschy, ensuring there’s something to suit every aesthetic taste. The craft market is free to enter and is open to the public from 11am-6pm.

LOCATION Oregon Convention Center, Portland DATES 2 May 2020, 12-13 Dec 2020

A visitor peruses jewellery at Crafty Wonderland (Photo: Crafty Wonderland)

Bridgetown Bluegrass Festival

Now into its 4th year, The Bridgetown Bluegrass Festival is a day long celebration of bluegrass and traditional music featuring performers that represent the future of the genre. Held at the historic First Congregational Concert Hall in the heart of downtown Portland, the festival will host over fifteen bands on two stages as well as offering craft beer and cider, food carts, instructional classes, booths for vendors and artisans, and plenty of room for jamming. This is an all ages event.

LOCATION First Congregational Concert Hall, Portland DATES 9 May 2020 

A stage performance at Bridgetown Bluegrass Festival (Photo: Bridgetown Bluegrass Festival)

UFO Festival

Given the preoccupation of so many Americans with the possibility of extra-terrestrial life, it’s hard to know quite how laced with irony this quirky festival actually is. The best advice is probably to go with an open mind and enjoy the wacky costumes, novel floats, movie screenings, outdoor music and special guest speakers, all contributing to the enduring debate about whether we really are or are not “alone”.

LOCATION Hotel Oregon, McMinnville, Yamhill County DATES 13 May 2020 

Revellers dressed as aliens ride a motorbike during a UFO Festival parade (Photo: Bruce Fingerhood via Flickr / CC BY 2.0)

Portland Pride Festival

Held in Portland since the early 1970’s, more than 200 groups participate in this afternoon-long celebration of sexuality, inclusion, friendship, music and colour in a safe, open and non-judgemental environment. The event is centred around a stunning parade, which is followed by a festival in Tom McCall Waterfront Park that’s packed full of Pride-themed activities.

LOCATION Tom McCall Waterfront Park, Portland DATES 1 June 2020 

Portland Rose Festival

Portland is known as the “City of Roses” because the weather is ideal for growing them, and each year the city celebrates this geographic quirk with a magical festival featuring fireworks, dragon boat races, parades and more. One of the main highlights is the Grand Floral Parade, which delights crowds with around 20 meticulously decorated floats, marching bands, equestrian units, vintage vehicles and colourful dancers.

LOCATION Venues across Portland DATES 4-5 June 2020 

A lady on horseback at a Portland Rose Festival parade (Photo: April L. Sanders via Flickr / CC BY 2.0)

Lake Oswego Festival of the Arts

Offering entertainment and education for all ages, each year the Lake Oswego Festival of the Arts brings together artists from across the globe who come to showcase over 1,000 pieces of art work in front of captivated crowds of art lovers. There are also multiple food vendors, music stages and a dedicated wine & beer tent to keep visitors both engaged and refreshed.

LOCATION Lakewood Center for the Arts, Lake Oswego DATES 26-28 June

Waterfront Blues Festival

Top class blues, soul and funk performers take to several stages at this popular outdoor music festival to entertain the crowds with their sublime sounds. Held along the west bank of the Willamette River in downtown Portland, the festival has been a mainstay on the city’s cultural calendar for almost 30 years and continues to be one of the region’s best live music events thanks to its consistently impressive line-ups of musical acts and inclusive atmosphere.

LOCATION Tom McCall Waterfront Park, Portland DATES 2-5 July 2020 

Oregon Country Fair

After celebrating its 50th anniversary last year, Oregon Country Fair is back for 2020 promising to be bigger and better than ever. Once again the annual festival will be packed full of fun-filled activities and entertainment, with live magic shows, music performances, artwork and kids’ amusements ensuring there’s something for every taste.

LOCATION Veneta DATES 10-12 July 2020

Extravagantly dressed visitors at Oregon Country Fair (Photo: R. Miller via Flickr / CC BY 2.0)

Oregon Brewers Festival

One of American’s longest running and most cherished craft beer festivals, the Oregon Brewers Festival offers a chance to celebrate the state’s vibrant beer brewing scene as well as showcase brews hailing from across the globe. Tents are erected throughout Waterfront Park and are dotted with craft beer stalls ready and waiting for the patronage of beer-loving visitors keen to sample some of the locally and internationally produced produce.

LOCATION Tom McCall Waterfront Park, Portland DATES 22-25 July 2020 

Providence Bridge Pedal

The 25th annual edition of the Providence Bridge Pedal comes to downtown Portland this year, seeing thousands of cyclists taking to the roads to traverse some of the city’s typically car-filled streets, which are closed off to all types of vehicles except bicycles for the occasion. Spectators can come and enjoy the spectacle from along the route.

LOCATION Downtown Portland DATES 9 August 2020

Oregon State Fair

State fairs are always a memorable occasion and Oregon’s is no different. Featuring aisles and aisles of livestock – from cattle, to sheep, to pigs – visitors have the chance to immerse themselves in Oregon’s time-honoured rural trades and traditions. There are magic and music shows, including classic rock and country performers, plus exhibition halls dotted with top class visual art, bakery treats, sewing, woodwork, and more.

LOCATION Oregon State Fairgrounds, Salem DATES 28 August-7 September 2020

A Ferris wheel takes centre stage at Oregon State Fair (Photo: Kirt Edblom via Flickr / CC BY-SA 2.0)

Rose City Comic Con

The cult of the comic continues unabated around the world and Austin’s contribution to this global phenomenon is the Rose City Comic Con. Some 70,000 fans descend on the event each year, many of whom come dressed as their favourite comic book character. The convention also features celebrities and special guests, hosting panels, cosplay fashion shows, memorabilia booths and gaming tournaments.

LOCATION Oregon Convention Center, Portland DATES 11-13 September 2020

Mount Angel Oktoberfest

The tiny Willamette Valley town of Mount Angel is an unlikely candidate for an Oktoberfest celebration, but for more than half-a-century it has played host to the region’s largest folk festival of its kind, attracting more than 300,000 revellers every year. Visitors can enjoy mouth-watering German food, music and beer, all set against the backdrop of a cosy community atmosphere.

LOCATION Mount Angel, Marion County DATES 17-20 September 2020

Sidewalk Chalk Art Festival

More often than not, street art is frowned upon as an eyesore, but few would place the fruits of the Sidewalk Chalk Art Festival into that category. Hosted by the Valley Art Association for almost three decades, the event invites artists of all abilities to grab a square of sidewalk and put their creative talents to the test, all to the delight of passers-by.

LOCATION Downtown Forest Grove, Washington County DATES 19 September 2020

A man puts his artistic talents to work at the Sidewalk Chalk Art Festival (Photo: Baker County Tourism via Flickr / CC BY-ND 2.0)

Portland Marathon

Portland’s largest road race sees thousands of runners hoping to score their personal best times, or perhaps simply to make it to the end of the strenuous 26.2-mile course. Spectators can come and watch all of the action from various vantage points along the route, or, if they’re feeling up to the challenge, can even participate themselves.

LOCATION Southwest Naito Parkway, Portland DATES 3 October 2020

Fall Kite Festival

Flying kites played a major role in many of our childhoods and this festival gives adults and kids alike the chance to enjoy the magical spectacle of hundreds of colourful kites dancing in the sky. Taking place in the scenic surroundings of Lincoln City’s sandy beach, the annual show also features expert demonstrations, kite-making workshops, and a parade.

LOCATION Lincoln City 3-4 October 2020

Kites flutter in the wind over the beach at the Fall Kite Festival (Photo: OCVA via Flickr / CC BY-ND 2.0)

The Portland Book Festival

Billed as the Pacific Northwest’s largest celebration of books and writing, the Portland Book Festival – formerly wittily known as ‘Wordstock’ – the festival offers literary lovers the chance to meet acclaimed authors, get their books autographed and listen to live recitals and readings. There’s also ample opportunity to peruse and purchase from a diverse assortment of books, magazines, comics, and other literary work.

LOCATION Portland Art Museum DATES 7 November 2020

Pioneer Courthouse Square Tree Lighting Ceremony

Each year, thousands of enthusiastic locals gather at Pioneer Courthouse Square to celebrate the lighting of an eye-catching 75 foot Christmas tree decorated with over 14,000 colorful lights, as well as join in with the city’s largest community sing-a-long, complete with everyone’s favourite Christmas carols. Pre-show entertainment begins late afternoon.

LOCATION Pioneer Courthouse Square, Portland DATES 27 November 2020

Holiday Ale Festival

A Portland holiday tradition, the Holiday Ale Festival is an outdoor annual event that sees beer lovers flock to huddle around gas heaters and enjoy the region’s largest decorated Christmas tree along with 50+ delectable winter ales being served. To try out the ales, patrons buy a souvenir mug and pay a minimal fee per sample. Food and craft vendors, a root beer garden, and seasonal music add to the fun.

LOCATION Pioneer Courthouse Square, Portland DATES 2-6 December 2020

Patrons pose for a photo at the Holiday Ale Festival (Photo: Reed Probus via Flickr / CC BY 2.0)

Tuba Christmas 30th Anniversary

One of the most enjoyable times of the year to visit Portland is December, when throughout the month there are unique events that imbue the city with a festive atmosphere. Among them are Tuba Christmas, which offers visitors the chance to listen to 200+ tubas play Christmas carols in Pioneery Square, downtown Portland. Attendance is completely free of charge.

LOCATION Pioneer Courthouse Square, Portland DATES 14 December 2020