The Best Festivals & Fairs in Portland & Oregon

by Paul Joseph  |  Updated February 2, 2024

There are a vast number of festivals and fairs that take place across Oregon throughout the year, many of which are hosted in its largest city of Portland.

A chef plating up at the Oregon Truffle Festival (Photo: Oregon Truffle Festival)

The Pacific Northwest state is renowned for its natural beauty, characterised by abundant forests, dramatic mountains, and idyllic beaches. Portland, meanwhile, attracts visitors with its offering of great outdoor living combined with a rich cultural and entertainment scene, most notably in the fields of art, theatre and music. If you’re planning a trip to Oregon 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 held in Oregon and Portland each year.

Oregon Truffle Festival

World-class wines and mouth-watering truffles make the Willamette Valley an acclaimed region for dedicated gastronomes the world over. Each winter – peak season for truffle-hunting – the Oregon Truffle Festival pays homage to its fertile soil across two weekends of celebrations, with visitors flocking to the valley and its surrounding areas to seek out and sample the four distinct varieties of native Oregon truffles, as well as to meet and engage with an ever-growing community of artisan food producers, chefs, speakers, industry experts and truffle growers.

Venues across Eugene / January-February 

Portland Winter Light Festival

Bringing light to the wintry darkness, each year more than 100 gifted media artists descend on Portland to put on captivating light installations, imaginative projections, and interactive displays at the Portland Winter Light Festival. Based around a different theme at every edition, the annual event creates an immersive experience for all, with live ice sculpture carving and artist talks to enjoy, together with the various arts exhibits. Admission to the  festival is free of charge for all.

Venues across Portland / February

Eye-catching balloons at the Portland Winter Light Festival (Photo: Sam Churchill via Flickr / CC BY 2.0 DEED)

Portland Jazz Festival

The Biamp Portland Jazz Festival is the largest jazz festival in the Pacific Northwest, comprised of over 75 events, including headline concerts and multiple free community events: live shows, workshops, and jazz conversations and lectures. Produced and presented by PDX Jazz during the last week of February and first week of March each year, the festival is a two-week music extravaganza that takes place in over 30 venues across Portland. Recognised as one of the top jazz festivals in the nation, the festival features artists spanning the full breadth of jazz and associated genres. Artists who are driving the evolution of jazz figure prominently alongside NEA Jazz Masters and GRAMMY Award-Winners.

Venues across Portland / February – March

A live performance at the Portland Jazz Festival (Photo: Camille Bruya)

Oregon Chocolate Festival

Humans have been infatuated with chocolate for thousands of years and visitors to Oregon in early March each year have the chance to worship at the temple of the sacred cocoa bean at this acclaimed festival. Regional chocolatiers, artisan food producers and other taste makers participate in a range of chocolate-themed 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 5k & 10k runs to help burn off those calories.

Ashland Hills Hotel & Suites, Ashland / March

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

Fertile Ground Festival

Organised by the Portland Area Theatre Alliance, this festival sees multiple Portland 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 eagle-eyed talent spotters and members of the public alike. 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.

Venues across Portland / April

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

Bridgetown Bluegrass & Folk Festival

Portland’s Bridgetown Bluegrass & Folk Festival, established in 2016, is a non-profit passionately dedicated to preserving traditional music. Held in the heart of Portland’s downtown arts district, its organisers foster the growth of this musical heritage by supporting talented artists, offering educational programs to the public, and hosting an annual day-long community event. With 15 incredible bands, enriching classes, and a vibrant atmosphere, our festival is a celebration of cultural roots. Experience the harmony of live performances while enjoying a selection of beverages, including beer, wine, and cider, along with delectable options from food carts, during a soulful journey into the heart of Portland’s music scene.

First Congregational Concert Hall, Portland / May

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

UFO Festival

Given the enduring fascination of so many Americans – and not just Americans, it should be said – with the possibility that extra-terrestrial life is out there, 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, thought-provoking movie screenings, outdoor music and special guest speakers, all contributing to the enduring debate about whether we really are or are not “alone”.

Hotel Oregon, McMinnville, Yamhill County / May 

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

Portland Rose Festival 

Known as the “City of Roses” owing to the local climate that makes growing the distinctive flower here so easy, each year Portland celebrates this happy geological quirk with a captivating festival featuring fireworks, dragon boat races, parades and plenty more. One of the event’s 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.

Venues across Portland / June

A lady on horseback at a Portland Rose Festival parade (Photo: April L. Sanders 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 visitors a chance to celebrate the state’s vibrant beer brewing scene as well as to sample brews hailing from across the globe. Tents are erected throughout Portland’s Waterfront Park and are dotted with craft beer stalls ready and waiting for the patronage of beer-loving aficionados keen to try some of the mouth-watering locally and internationally produced produce.

Tom McCall Waterfront Park, Portland / June-July

Portland Pride Waterfront Festival and Parade

Held in Portland since the early 1970’s, more than 200 groups participate in this weekend-long celebration of sexuality, inclusion, friendship, music and community in a safe, open and non-judgemental environment. Attracting tens of thousands of visitors each year, the main festival event takes place in Tom McCall Waterfront Park and is packed full of food, drink, live music and a multitude of Pride-themed activities, followed by a stunning parade through downtown Portland on the Sunday.

Tom McCall Waterfront Park, Portland / July

Revellers line the parade route at the Portland Pride Waterfront Festival and Parade (Photo: Portland Pride Waterfront Festival and Parade)

Oregon Coast Music Festival

The annual Oregon Coast Music Festival features more than a dozen unique musical experiences in unique indoor and outdoor locations throughout the Coos Bay region  Additional concerts and workshops are planned. Over two full weeks, musical performances are scheduled at large and small venues and feature such notable names as American Band Music, Jazz Favorites, Chamber Music, Music from the Cinema, and African Marimba Music.  Meanwhile the famous OCMA Festival Orchestra provides three concerts with an 80-piece orchestra during the last week.

Venues across Coos Bay / July

(Photo: Oregon Coast Music Festival)

Waterfront Blues Festival

Top class blues, soul and funk performers take to several stages at this popular outdoor music festival to entertain packed crowds of music lovers with their sublime sounds. Held along the scenic 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 stellar line-ups of acts together with a welcoming, friendly and inclusive atmosphere.

Tom McCall Waterfront Park, Portland / July 

Oregon Country Fair

Pretty much every state across America has its own country fair featuring tractor pulls, farm animals and a whole lot more – and Oregon is no different. Held at the start of July each year in the wooded environs of the Willamette Valley, situated a couple of hours by road from Portland, the event includes food vendors, live music, educational zones and craft booths. But what really makes this fair unique are the hippy vibes created by the many attendees who come adorned in elaborate costumes and body-paint for the occasion.

Veneta / July 

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

Oregon State Fair

Quintessentially American, state fairs are always a memorable occasion and Oregon’s contribution to these action-packed events 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 and agricultural 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.

Oregon State Fairgrounds, Salem / August-September 

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 enduring cult of the comic continues unabated around the world and Portland’s contribution to this global phenomenon is the Rose City Comic Con. Founded back in 2011, the pop culture convention has gone from strength to strength and now routinely sees some 60,000 fans descend on the Oregon Convention Center each year, many of whom come dressed as their favourite comic book characters for the occasion. The event also features celebrities and com creator guests, programming panels, cosplay competitions, memorabilia booths, gaming tournaments, and much more.

Oregon Convention Center, Portland / September 

Costumed participants at the Rose City Comic Con (Photo: Rose City Comic Con)

Mount Angel Oktoberfest

It’s fair to say that 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. Inspired by the original German Oktoberfests that date all the way back to early 19th-century Bavaria, visitors can enjoy authentic German food, music and beer, all set against the backdrop of a cosy community atmosphere.

Mount Angel, Marion County / September

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 relive those halcyon days by enjoying the magical spectacle of hundreds of colourful kites dancing in the sky. Taking place in the picturesque surroundings of Lincoln City’s sandy beach at the D River State Recreation Site, the popular annual show also features expert demonstrations, kite-making workshops, an art kite display, a kite flier memorial and a parade.

 D River State Recreation Site, Lincoln City / September

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 regional wineries as they enjoy a whistlestop tour of local art galleries, shops, restaurants and hotels.

Venues across Cannon Beach / October

The Portland Book Festival

Billed as the Pacific Northwest’s largest celebration of books, writing and the literary world as a whole, the Portland Book Festival – formerly known as ‘Wordstock’ (a witty play on words designed to appeal to its attendees) – the festival offers lovers of the written word 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 works.

Venues across downtown Portland / November