This ride is a good way to explore the Berkeley and Oakland Hills a bit without having to climb any of the really steep grades. I usually do this ride as a home-to-BART ride (starting in Rockridge and ending at a BART station) but you can tack on an extra 15 miles and make it a full loop if you really want.
Start in Rockrige or North Berkeley and head over to Spruce Street (I take Milva to Rose to Spruce, but do it the way you like). Climb Spruce to enter Tilden park, and follow Wildcat Canyon Road/East Park Drive past Inspiration Point and down to Camino Pablo. Take Camino Pablo/Moraga Way through Orinda and Moraga until you get to Canyon Road. This is a good resting point, as there are plenty of places to fuel up and take a bio break. The gas station on the corner has a restroom, but if you want a nicer restroom, turn left on Moraga Road and proceed about a quarter of a mile to the Moraga Commons Park, at the Lafayette-Moraga Regional Trail head where Moraga Road meets St Mary's Road. Nicest public restrooms in the bay area.
After resting, head down Canyon Road until you get to Pinehurst Road. If you turn right on Pinehurst, you'll have a lovely climb through Redwood forest culminating in a hideously steep section before you get dumped onto Skyline. Very scenic, very popular route, but that's for another day. Instead, turn left on Pinehurst.
The first half mile on Pinehurst takes you through Redwood forest, but it quickly opens up to slightly more arrid vegetation. It's still scenic, but it's not as shaded as the other section of Pinehurst, so it can heat up quickly. The climb up Pinehurst is pleasantly graded and lasts for a mile or two. After a brief descent, turn left onto Redwood Road. Redwood Road follows the eastern ridge of the Oakland Hills all the way to Castro Valley. It's another nice gradual climb with hardly any steep sections.
After 15 miles through the hills, it's a bit jarring to end up in Castro Valley, but if it's around lunch time then it's a good excuse to stop at one of the few bright spots in CV: Luccas Italian Deli. From Redwood Road, turn right on Castro Valley Blvd and in about two blocks you'll see Luccas on the left side of the boulevard. Great sandwiches, friendly people, and popular with locals.
Alright, after lunch, continue on Castro Valley Blvd and make a right on Lake Chabot Road. At the lake, vear right to stay on the road for a scenic two mile lake-view stretch. As you leave the lake behind, continue on Estudillo for a couple of blocks and make a left on Bancroft.* Then turn right on Dolores and follow it all the way to the San Leandro BART station.
*note: If you want to tack on extra miles, you can make a right on Bancroft and ride into downtown Oakland. However, this section of town is definitely not scenic and is possibly not quite very safe. I've ridden this route many times and have never exactly felt unsafe, but it's really not the route you'd take your family and friends on. But if you really need those extra miles: take Bancroft until it becomes Bond, go left on 42nd Ave., right on International, left on 40th Ave., and right on E 12th Street. This will take you to Fruitvale BART. Continue further on E 12th street to get to Lake Merritt and downtown Oakland.
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