May 2 – 4
Pioneer Family Festival
Information: www.pioneerfamilyfestival.itgo.com

A weekend of family fun at Clackamette Park in Oregon City featuring, Rides, Food, Live Music, Art & Pony Rides.  There will be a Skate & BMX Competition followed by the Teddy Bear Parade.

 

May 3 – 4
Faire in the Grove
Information: http://www.faireinthegrove.com/WhoWhatWhen.html

Medieval Re-enactors, Armored Fighters & History Buffs, who invite you to experience the Middle Ages and the Renaissance! Hosted on the vast front lawn of the McMenamins Grand Lodge, come and be transported back to Fairegrove, a medieval village.  Enjoy seeing and learning some of the history behind life in the middle ages and beyond into the Renaissance.

 

May 3 – 5
Cinco de Mayo Fiesta
Information: http://cincodemayo.org/

Portland Guadalajara Sister City Association presents the 30th annual Cinco de Mayo Fiesta at Waterfront Park.  Come Enjoy Live Entertainment, Authentic Foods & Drink, Rides, Games and Family Fun.

 

May 8 – 11
2014 Bridgetown Comedy Festival
Information: www.bridgetowncomedy.com

Now in its 7th year, Bridgetown festival roster of performers features a blend of world-famous headliners, up-and-coming performers, and the Pacific Northwest’s top talent. Venues include the Doug Fir, the Alhambra Theater, the Hawthorne Theater and many more.  With a single wristband, you can see dozens of shows over the course of the weekend.  You can quickly hop from seeing a sold out show in a theater to seeing a national headliner in an intimate setting on a bar’s back patio.

 

May 10
Doggie Dash 2014
Information: https://www.oregonhumane.org/doggiedash/

Walk. Run. Be a Hero.  The Doggie Dash is an annual event to raise money for the Oregon Humane Society.  Bring your furry friend and choose between two Courses; the 1.5 mile “Doggie Dash Classic” or the 2.5 mile “Bridge to Bridge”

 

May 11
Mother’s Day White Rabbit Buffet
Information: http://www.mcmenamins.com/events/123018-Mothers-Day

Honor the special women in your life by bringing them to a special buffet & McMenamins Edgefield.  After brunch, check out the Edgefield Gardeners’ Plant Sale located by the greenhouse.

 

May 15 – 18
McMenamins UFO Festival
Information: http://ufofest.com/

This year marks the 15th Annual UFO Festival.  Experience a truly extraordinary line up of guests – from an internationally known talk-show host to an expert in the Sasquatch/extraterrestrial phenomena and beyond….  There will also be a UFO costume parade, multiple live bands and much more.

 

May 17
German Maifest at Oaks Park
Information: http://www.afportland.org/2014/04/franco-german-maifest-with-zeitgeist/

There will be vendors, artists and special programs for kids throughout the day.  Visitors will be able to enjoy the German and French languages as well as food, musical performances & dance groups.

 

May 16 – 17
Sesame Street Live – Veterans Memorial Coliseum
Information: http://www.rosequarter.com/events/detail/sesame-street-live

Elmo, Grover, Abby Cadabby and their Sesame Street friends welcome Chamki, Grover’s friend from India to Sesame Street.  Join in the fun and make a memory with your friends & family.

 

May 17
Stars on Ice
Information: http://www.rosequarter.com/events/detail/stars-on-ice

America’s top Olympic medal contenders from the 2014 winter games in Sochi headline this seasons all-new Stars on Ice Tour.  Experience the passion and relive the spirit of the US Figure Staking Team as they celebrate their performances from the 2014 Winter Games.

 

May 18
Rock ’n’ Roll Portland ½ Marathon
Information: http://runrocknroll.competitor.com/portland

The scenic half marathon course starts and finishes Downtown adjacent to Waterfront Park.  After the race, reunite with family and friends in the Family Reunion area and relish in your post-race accomplishment with refreshments and live music at the finish line stage.

 

May 23
Rose Festival CityFair Begins & Fireworks
Information: www.rosefestival.org

Portland’s waterfront comes alive with fun and festivities during the Rose Festival CityFair, part of Portland’s official festival. Fair-goers can enjoy exciting midway rides, live music in the RoZone, local beer and tasty treats, exotic animal displays, a wide variety of shopping, and many other special attractions.  It all starts with a spectacular fireworks starting around 10:00pm.

 

May 30
James Taylor
Information: http://www.rosequarter.com/events/detail/james-taylor

James Taylor and his band are coming to the Moda Center for one intimate and memorable night.

 

May 31
Starlight Run
Information: www.rosefestival.org/event/starlight-run

Portland’s most popular Fun Run is cheered by more than 250,000 spectators who line the 3.1-mile Starlight Parade route to see the costumed competition up close.  With more than 4,000 runners is not only the largest Fun Run in Oregon, but the most entertaining – with participants vying not only to break the tape, but to claim prizes (and bragging rights) for best individual and group costumes.

 

May 31
Starlight Parade
Information:  www.rosefestival.org/event/starlight-parade

One of our most popular events, the Portland General Electric/SOLVE Starlight Parade offers funky, eclectic fun for everyone. From traditional marching bands and flood-lit floats, to glow-in-the-dark umbrellas and unique hand-built entries, you’ll see the best of Portland’s diverse community groups (and surrounding Northwest region) together in one whimsical pageant.