Rosarito–Ensenada Bike Ride

Celebrating its 34th anniversary is the Rosarito–Ensenada bike ride, a 50-mile fun trek that happens twice annually, this year on May 3 and September 27. In what’s billed as one of the largest cycling events in the world, nearly 4,000 participants follow the free road out of Rosarito south along the coast before cutting inland at La Mision and upward through the hills surrounding the Valle de Guadalupe wine country and onward to Ensenada. At the finish line is a street fest with food, bands, and beer. If you don’t want to haul your wheels to Mexico, TNT Ensenada (tntbicicletas.com) rents loaners, and shuttles run back to Rosarito from Ensenada after the race for $22 per cyclist. Preregister online for 400 pesos ($35), or sign up on the day of the ride for 450 pesos ($40).

Getting from San Diego to the border by bike is a 30-mile tour—and an epic one at that (how many bike rides cross international borders?). Cruise the Bayshore Bikeway, a 25-mile loop linking Chula Vista, Imperial Beach, Barrio Logan, and the Silver Strand via the San Diego– Coronado Bay Bridge (the ferry makes for a less-strenuous option), and skim the horse ranches and farms of the Tijuana River Valley before eventually finding yourself face to face with Mexico on the horizon. Even if it’s just to walk your bike across for a quick taco and bag of churros before heading back north.

Ease into riding south of the border with Paseo de Todos Tijuana, a night group ride that departs from beneath the arch on Avenida Revolucion at 8 p.m. the first Friday of the month and occasionally hosts cross-border rides that usually depart from a San Diego bar.