Caution: Sweeping views of Bay icons (the San Francisco skyline, Alcatraz and Golden Gate Bridge) make it hard to keep your eyes on the road for this scenic East Bay pedal in the hills. The moderate 29-mile road loop is enjoyable for first-timers and roadie warhorses alike: The climbs aren’t too long and car traffic is surprisingly sparse. Start in small-town Orinda and cruise south, passing under crisp yellow and orange foliage fit for the fall season. Soon you’ll be rolling along a quiet backcountry road bordering Redwood Regional Park. The first big Bay views come after climbing along Skyline Boulevard. Things keep looking up from there: The views stick with you as you cruise atop the ridge of Skyline and Grizzly Peak Road through Tilden Regional Park. Inspiration Point is the last chance for reveling in the view before descending back to Orinda. Whoop-de-loop!
Park in downtown Orinda where there’s loads of (gasp!) non-metered parking spots and no weekend time limits. Go south on Moraga Way for 4.5 miles. At Canyon Rd. in Moraga, go right. Continue for 2 miles; at Pinehurst, go left. Stay on Pinehurst for 3 miles, then go right on Redwood Rd. Continue on Redwood for 2.4 miles. Turn right onto Skyline Blvd. After .5 mile, go right to stay on Skyline near Joaquin Miller Park. Stay on Skyline for another 5.2 miles. At Grizzly Peak Rd., go right. Continue on Grizzly Peak for 3.8 miles. Just past the Tilden Park steam trains, go right onto South Park Rd. for 1.5 miles. Turn right on Wildcat Canyon Rd. and go 3.5 miles–passing Inspiration Point. At Camino Pablo Rd., turn right and go 2 miles into downtown Orinda.