The Cinco de Mayo Fiesta (www.cincodemayo.org ) celebrates Hispanic heritage at Tom McCall Waterfront Park  the first weekend (including Thurs.–Fri.) in May. This has become one of the largest celebrations of its kind in the country. Mariachis, folk-dance exhibitions, a large selection of Mexican food, and fireworks displays are included in the festivities. Admission is $8 adults, $2 children ages 4–11.
The Portland Rose Festival (503/227-2681, www.rosefestival.org ) has been Portland ’s major summer event for nine decades. The Rose Queen and her court (chosen from among local high school entrants), sailors and prostitutes, and floats from several parades clog Portland’s traffic arteries during this 18-day citywide celebration each June.
Air shows, a hot-air balloon classic, the Indy World Series car race, and a traditional rose show round out the main attractions. Check out the website for a schedule of what is essentially a small-town festival done with big-town flair.
Even if parades and crowds are not your thing, the civic pride here is genuine and appealing. Portlanders camp out along the parade route in the same places year after year, sometimes several days in advance, just to catch a coveted glimpse at the floats passing by.
The key to enjoying festival events is avoiding traffic and parking hassles. A $4.75 TriMet day ticket entitles the pass-holder to unlimited rides on MAX, the Portland Streetcar, or the bus all day long. As for traffic, be especially wary of the waterfront. Such festival features as food booths and carnival rides in Tom McCall Waterfront Park , as well as military ship displays on the Willamette, draw huge crowds.
Another good reason to come to the waterfront is the chance to see the dragon boat races. These brightly painted ceremonial canoes from China have been taken up in earnest here. Teams compete on the Willamette River with 16 paddlers and a coxswain.
Two of the more colorful events of the June fete are the Grand Floral Parade and the Festival of Flowers at Pioneer Courthouse Square . In the latter, all manner of colorful blossoms fill the square to overflowing during the first week of the festival.
The Grand Floral Parade usually begins the Saturday following the opening of the festival. You can reserve seats in the Coliseum ahead of time, but save your money and station yourself on an upper floor along the parade route or visit the floats at Oregon Square between Lloyd Center and the Convention Center  during the week following the parade. Any lofty perch is sufficient for taking in all the hoopla, drill teams, the Rose Queen, and equestrian demonstrations.
This procession is the second-largest all-floral parade in the United States.
Portland  is a bicycle town that loves a festival, but it questions authority. Put this all together and you get Pedalpalooza (www.shift2bikes.org/pedalpalooza ), a decentralized, even anarchic celebration of Portland’s bike culture. The festival is extremely freeform and is held in multiple locations with only a few organized annual events, but there are many other events that are just someone’s idea for a ride or crazy stunt that involves a bike. Events included the infamous Naked Bike Ride (the largest in the United States), the Cirque de Cycling Parade, bicycle jousting, and a biking-themed film festival that includes a “Bikesploitation” series of biking porn films.
The two-week festival is held in mid-June; check the website for events, as Pedalpalooza is growing and evolving fast. There is more fun and nudity than at the Rose Festival!
The Waterfront Blues Festival (503/282-0555, www.waterfrontbluesfest.com ) is the largest festival of its kind on the West Coast. It takes place the first weekend in July at Tom McCall Waterfront Park , and many famous artists attend. The $10 admission and donations (two canned-good items) go to the Oregon Food Bank.
From the end of June through July, Chamber Music Northwest (503/294-6400, www.cmnw.org ) presents five weeks of classical music concerts in two locations: Reed College in Southeast Portland  and Catlin Gabel School in Northwest Portland . Ticket prices begin at $25.
No longer Gay Pride, not even Gay and Lesbian Pride, it’s now just the Pride Festival (503/295-9788, www.pridenw.org ): Portland ’s largest gay festival celebrates Stonewall and affirms the city’s lesbian, gay, bi, trans, and queer community, held on Father’s Day weekend in June. Saturday brings a number of parades plus entertainment at the Waterfront Park main stage. Sunday is the big day, however, starting out with the Pride Parade, with some 50,000 people in attendance, followed by speakers and entertainment at Waterfront Park.
The Mount Hood Jazz Festival (503/665-2837, www.mthoodjazz.com ) is the summer event for jazz and blues connoisseurs. World-renowned jazz artists converge the first weekend of August at Mount Hood Community College in Gresham, 20 minutes east of downtown Portland. You’ll need to buy reserved tickets ($32) for the evening concerts in the air-conditioned College Theater, while outdoor concerts from the courtyard stage are free.
For summer outdoor concerts, it’s all happening at the Oregon Zoo  (503/280-2493, www.oregonzoo.org/Concerts/ , late June–late Aug., $11–22). Crowds spread out on the lawn below the stage to hear first-rate, often big-name talent.
Taking place the last full weekend in July in Portland’s Tom McCall Waterfront Park , Oregon Brewers Festival (www.oregonbrewfest.com ) is North America’s largest gathering of independent brewers. The four-day event showcases the wares of more than 80 breweries and attracts more than 72,000 beer lovers. Admission is free, but you’ll need to spend $10 for a souvenir mug and four drink tokens. Live musical entertainment accompanies the beer.
An August festival, The Bite of Oregon (Tom McCall Waterfront Park, 503/657-5382, www.biteoforegon.com ) lets you sample local culinary specialties of Portland restaurants, with the proceeds going to the Special Olympics. Live music is also featured.
Portland  dares to compare its live music scene to Austin, Texas, and the citywide Music Fest Northwest (www.musicfestnw.com ) is Portland’s answer to Austin’s South by Southwest Festival. Over the course of four days and nights in early September, over 200 bands gather in Portland to play their music for large and enthusiastic audiences. The festival is held at sites across the city; pretty much all the major nightclubs and live music venues are involved. To attend the concerts, you’ll need to buy a $50 wristband, which gets you into any concert and any venue.