Rule the Empire

Cycle Yucaipa and Redlands

01.26.2016

It's an Inland Empire classic and it will test your pedal mettle. This 28-mile lollipop-loop tour of Yucaipa and Redlands features high mountain scenery and palm-lined boulevards, where views of the San Bernardino Mountains meet streets rich with history. From Yucaipa Community Park zigzag uphill to Pendleton Road, one of coolest roads in town with big views of the Yucaipa Valley. Pedal your way over to Crafton Hills College for a one-mile descent through Sand Canyon to remnant orange groves in east Redlands. Drop down to the historic Kimberly Crest House, former digs of one of Redlands' early visionaries. From here, coast nearly pedal-free to the lively downtown Redlands area (the à la minute ice cream shop has delectable rest-stop temptations, including creative flavors like chocolate lavender and olive oil vanilla bean). A marked bike lane on Brookside Avenue and wide-shouldered streets lead back to stunning Victorian homes along Highland Avenue at the base of the hills. Ogle the vintage digs and grunt up a tough but scenic climb to Sunset Drive. Stately mansions and faraway vistas wind along Sunset high above Redlands, accompanied by swerve-worthy valley and mountain views to a jump across I-10 and back to the homestretch to Yucaipa Park.

From the I-10 freeway, exit at Oak Glen Rd. Go 4.3 miles to a left turn into Yucaipa Community Park. Back on Oak Glen, ride 0.75 mile to Bryant St. Turn right and roll 0.5 mile to Date Ave. Go left, ride up to Fremont St. and turn right. At Pendleton Rd. go left and roll for just over 1 mile to Oak Glen Rd. and turn left. Go 1.75 miles to the trailhead; catch the bike path on the north side of Oak Glen, and spin 1.4 miles to Chapman Heights Rd. Go right to Sand Canyon Rd. and ride 1.8 miles to its junction with 5th Ave. Go 2 miles to Highland Ave and another 1 mile to Cajon St. Turn right and in 1 mile turn left at Citrus Ave. (Citrus becomes Brookside Ave. in one block.) Ride 1 mile on Brookside to San Mateo St. and turn left. Climb 1.2 miles to Highland Ave. and turn left, reaching Center St. in 0.5 mile. Go right, climbing 0.9 mile to Ridge St. A right turn heads uphill to Sunset Dr. S. Ride 3.2 miles (continue straight onto Alta Vista when Sunset Dr. veers left) to Highview Dr. and turn right, snaking through the neighborhood (left on Avenue N, right on Florida, left on 17th St.) to Outer Highway 10. Turn right and in 0.2 mile go left across the interstate. Follow 16th St. for 0.6 mile to Ave. D and go right. In 1.5 miles turn left on 10th St. to reach Yucaipa Blvd. Continue on 10th St. 0.6 mile to Chapman Heights Rd. Turn right and retrace to Oak Glen and the final 1.5 miles to the park.

Trending Stories NorCal

View all Stories
  1. Perles Beach Angel Island San Francisco Bay

    Secret Beach

    A hidden beach and a killer view? Those are hard to come by, but that’s exactly what you’ll get at Perles Beach on Angel Island. Bike or hike to this beautiful pocket cove.

    View

  2. Cinematic Sonoma

    Longer days. Golden light. Wildflowers in bloom. It’s the perfect moment to plan your spring escape to Sonoma for the Sonoma International Film Festival, March 25–29. No fuss. No sprawl. Just films, friends, fresh air, and that unmistakable Sonoma glow.

    View
  3. Hike Pescadero Marsh Natural Preserve

    Mellow in the Marsh

    Beach, birds, ice plant popping purple flowers: That’s a hiking slam dunk! Hike about 2 miles at Pescadero Marsh Natural Preserve using their easy to navigate (well-signed) Sequoia Audubon Trail.

    View
  4. A man is looking through his binoculars at sunrise at the Bayland Nature Preserve in Palo Alto

    Baylands Bird & Art Loop

    Combine an outdoor art walk and wildlife sightings at the Baylands Nature Preserve in Palo Alto. This 5-mile loop through Byxbee Park and the Emily Renzel Wetlands features striking installations by artists Peter Richards and Michael Oppenheimer—where the landscape itself becomes part of the canvas.

    View

Trending Stories SoCal

View all Stories

  1. Tree Town

    Home to an estimated 21,000 trees and 100 acres of parkland, South Pasadena has earned its nickname: the City of Trees. This 2.5-mile neighborhood walk lets you experience its leafy canopy up close, winding through charming streets and three of the city’s beloved parks.

    View

  2. A Better Way to Baldwin

    The Baldwin Hills Scenic Overlook in Culver City is one of West L.A.’s most popular hiking spots, but most visitors miss the bigger picture. This 3.5-mile out-and-back along a section of the Park to Playa Trail offers a fuller experience of this gorgeous nature park with sweeping urban views and a few artistic surprises along the way.

    View
  3. Sponsored

    Warm Up to Winter in Reno Tahoe

    2026 is just getting started, but there’s one place already rising to the top as the best for adventure and relaxation: Reno Tahoe. The awe—and ahhhs—begin as soon as you arrive. G

    View
  4. A woman standing at the pond's edge at Ernest B Debs Regional Park in Los Angeles. Trees are making reflections on the pond.

    Urban Oasis Loop

    Home to the city’s Audubon Center, Ernest E. Debs' 282-acre park features a robust network of hiking trails and surprising wildlife diversity. More than 140 bird species have been spotted here. Birdwatcher or not, this 2.5-mile route makes for a gorgeous outing.

    View