June 4: Pioneer Century
Described as "the Eden at the end of the Oregon Trail," the 55-mile route on this ride will give you elevation gains of 3,087 feet. Rest stops, maps and road markings will lead you through the Cascade foothills and the Champoeg area. Clackamas Fairgrounds, 694 NE 4th Ave., Canby, pwtc.com. 9 am. $25.
June 4-5: Tour de Hood
Dying to know if you're tough enough for Mount Hood? These challenging, strenuous hill climbs are two of the same routes racers conquer during the Mount Hood Cycling Classic. The Scenic Gorge Loop is 42 miles and can be combined with the 71-mile Three Summits Challenge the next day. Begins 1 pm. $75-$160 (depending on registration date) at tourdehoodride.com.
June 8-July 13: Velo on the Volcano
The Oregon Bicycle Racing Association and River City Bicycles present six Wednesday-evening races on a hilly loop around the upper reservoir at Mount Tabor. Mount Tabor Park picnic shelter, Southeast 69th Avenue and Mount Tabor Court, www.mttaborseries.com. 5:50-8 pm Wednesdays. $15 per race, OBRA membership ($5 per day, $25 per year) required for racers.
June 9-26: Pedalpalooza
With nearly 300 events organized by individual cyclists, there's plenty of madness to choose from in June, including a naked ride, bike polo, a ginger ride for redheads, and a citywide scavenger hunt. A calendar of events can be found at shift2bikes.org.
June 12: Cirque du Cycling
Tall bikes, outlandish costumes, circus tricks and stilted men come together in a celebration of bicycles along Mississippi Avenue, benefiting Albina Youth Opportunity School. Show your love for all things two-wheeled (or one- or three-), with an art-bike parade (reportedly the largest in the country), a family bike ride, a high-speed bike race and beer gardens for viewing. North Mississippi Avenue between Shaver and Fremont streets, cyclingcircus.com. Noon-7 pm. Free.
June 12: Archdiocese of Portland Bike Blessing
Remembering those riders no longer with us, and praying for the safety of those still here, the bike blessing is open to anyone. St. Mary's Cathedral courtyard, 1716 NW Couch St., archdpdx.org. 2-2:30 pm. Free.
June 12: Sunny Nekkid Ride
A warm-up event for the World Naked Bike Ride, this daylight ride will take 100 or so riders through Laurelhurst. Joan of Arc statue, Northeast 39th Avenue and Glisan Street, wiki.worldnakedbikeride.org/wiki/Portland. 2 pm. Free.
June 12: Fig Leif Naked Run/Ride
A 10k naked off-road ride, for those who like to play fast and loose with their genitourinary systems. Leif Erickson Drive, 400 yards past the west end of Northwest Thurman Street, wiki.worldnakedbikeride.org/wiki/Portland. 7:30 pm. Free.
June 12: Gayest Day of the Year Ride
Join the Sexual and Gender Minority Youth Resource Center for a ride dedicated to supporting LGBTQ youth. Before the ride, decorate your bike while DJs and musicians perform, or pick up information from various LGBTQ organizations. Afterward, join the community barbecue. SMYRC, 3024 NE Martin Luther King Jr. Blvd., smyrc.org. Noon-3 pm. $10 suggested donation.
June 18: World Naked Bike Ride
Whether protesting fossil fuels and the vulnerability of cyclists or just exercising a need to lose some threads, 10,000 people stripped down for the 2010 WNBR. Even more are expected this year. Shoes and helmets are "strongly encouraged." Southeast Water Avenue and Salmon Street, wiki.worldnakedbikeride.org. 10 pm. Free.
June 18: Petal Pedal
Marked routes will lead you along quiet Willamette Valley roads to a dinner served in the Oregon Garden. Routes for different cycling abilities are set for 30, 68 or 100 miles. Begins at 879 W Main St., Silverton, petalpedal.com. 6 am. $70 in advance, $80 the day of the ride.
June 25: Multnomah County Bike Fair
Pedalpalooza concludes with a raucous celebration of Portland bike culture. Expect unicycle jousting, music and lots of vendors. Location to be announced, see shift2bikes.org. Noon-4 pm. Free.
June 26: North Portland Sunday Parkways
Eight miles of streets between Peninsula and McCoy parks will be closed to cars for five hours, with food, music and family activities in parks and on sidewalks along the route. 11 am-4 pm. See route at portlandsundayparkways.org.
July 15-17: Alpenrose Velodrome Challenge
In order to stay on the steepest oval velodrome track in the U.S., racers competing to win a $13,000 prize have to maintain speeds of at least 18 mph. Spectators watch for free. 6149 SW Shattuck Road, alpenrosechallenge.com. Events begin 11 am Friday.
July 24: Westside Sunday Parkways
Six miles of streets between Gov. Tom McCall Waterfront and Wallace parks will be closed to cars for five hours, with food, music and family activities in parks and on sidewalks along the route. 11 am-4 pm. See route at portlandsundayparkways.org.
Aug. 12: Portland Twilight Criterium
Closed-off blocks of Old Town streets are filled with spectators, food carts and activities, such as a hand-built bike show and a beer garden, all situated in the middle of the course of this high-speed street race. Free bike parking at Northwest Park Avenue and Flanders Street. North Park Blocks, Northwest 9th Avenue and Couch Street, portlandtwilight.com. Races begin 4 pm. $25-$30.
Aug. 14: Providence Bridge Pedal
Nearly 20,000 bicyclists and pedestrians fill Willamette River bridges to support the Providence Heart and Vascular Institute. Routes from 13 to 36 miles include the top decks of the Fremont and Marquam bridges. Southwest Salmon Street and 14th Avenue, blog.bridgepedal.com. 7 am. $25-$45.
Aug. 21: Portland Century
Take in the eye-catching views of Portland and surrounding areas such as Bull Run, Marine Drive and the Willamette Bluff while staying hydrated and on track. Choose the 40-, 75- or 100-mile route, with gourmet food and refreshments along the way. Ride begins at Portland State University behind Smith Memorial Student Union, Southwest Montgomery Street and Park Avenue, portlandcentury.com. Check-in times 6-9 am, depending on route. $70 in advance, $80 at event.
Aug. 27: Lancette Memorial Ride
A ride celebrating the life and ambitions of Teresa Wilson Beiser, a Tualatin woman who was murdered in 2009 by her estranged husband. Beiser's dream of becoming the next Lance Armstrong—thus "Lancette"—is commemorated in this 40-mile family ride and the 62-mile Lancette Metric benefit for Clackamas Women's Services. Ackerman Middle School, 350 SE 13th Ave., Canby, lancettememorialride.com. 6:30 am. $15-$50.
Aug. 28: Southeast Sunday Parkways
Six miles of streets between Buckman and Mount Tabor will be closed to cars for five hours, with food, music and family activities in parks and on sidewalks along the route, coinciding with the Hawthorne Street Fair. 11 am-4 pm. See route at portlandsundayparkways.org.
Sept. 11: Tour de Lab
Nothing says "I love you" to man's best friend better than a multi-pub bike tour to support DoveLewis Emergency Animal Hospital. A 30-mile route will take you to four brewpubs, but if even the thought of uphill pedaling gives you a nosebleed, the 18-mile route includes a flatter journey to three brewpubs. Dress as a dog or something a dog chases to be eligible for the costume contest. Lucky Labrador Beer Hall, 1945 NW Quimby St., tourdelab.com. 9:30 am. $35-$50.
Sept. 17: BikeToBeerFest
Hopworks hosts a bike-in Oktoberfest celebration, with five bands performing on a keg-supported stage, games and lots of beer. Hopworks Urban Brewery, 2944 SE Powell Blvd., 232-4677, hopworksbeer.com. Noon-10 pm. Entry fee TBA.
Sept. 25: Northeast Sunday Parkways
Eight miles of streets between Woodlawn Park and Northeast Cully Boulevard will be closed to cars for five hours, with food, music and family activities in parks and on sidewalks along the route. Noon-5 pm. See route at portlandsundayparkways.org.