Portland is the state's festivals hub, with many events taking place Downtown on the city's scenic Willamette riverfront, but you'll find plenty of engaging festivals elsewhere. Also keep in mind that Oregon is wild about farmers' markets—most towns in the state have one from spring through fall, and Portland has dozens. There's often live entertainment, arts and crafts, and prepared food at these bustling outdoor markets.
Spring. Portland's Cinco de Mayo festival celebrates its sister-city relationship with Guadalajara, Mexico, and runs a full weekend in early May. Arguably the most famous event in the state, the Portland Rose Festival consists of numerous events and parties throughout late May and early June, culminating in a huge parade.
Summer. Among the many big waterfront gatherings in Portland each summer, check out Portland Gay Pride in mid-June, the Waterfront Blues Festival over Fourth of July weekend, the Oregon Brewers Festival in late July, and the Bite of Oregon food festival in early August.
Wine lovers flock to McMinnville, in the Willamette Valley, to sample fine regional vintages in late July during the International Pinot Noir Celebration. Autumn is just around the corner with the arrival of the Oregon State Fair in Salem in late August and early September.
Fall. Since 2012, Portland's Feast has rapidly earned kudos as one of the most talked-about international culinary festivals in the country, with events and meals prepared by both local and national star chefs. The Pendleton Round-Up is one of the most prestigious and downright fun rodeos in the country, drawing more than 50,000 participants and spectators in September. In coastal Bandon each September, the Cranberry Festival comprises a fair and parade. The Sisters Folk Festivalbrings top-name artists to this scenic mountain town near Bend, which hosts its bustling Bend Fall Festival in mid-September.
Winter. Although it sounds like a short-term seasonal event, Ashland's famed Oregon Shakespeare Festival actually runs from late February through early November. In mid-February, Oregon WinterFest in Bend celebrates the region's winter sports with a mix of outdoors activities and indoor concerts. Late February's Newport Seafood and Wine Festival is a tasty time to visit the coast. Film lovers will enjoy the Portland International Film Festival, featuring works from throughout the world each February, which coincides with the acclaimed Portland Jazz Festival.