Quarantivities & Stories #7: Trails of Windemere

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  • The hilly 2.7-mile Dougherty Valley Ridge Trail offers a sprawling bird's-eye view of both the East Branch and Windemere Parkway sides of Windemere.

  • Steep, rolling hills and migratory cows are common features of Dougherty Valley Ridge Trail, yet they never fail to stun.

  • Rolling Hills Trail acts as a connector between the Camino Tassajara end of Windemere Parkway and the Ramona end of Tassajara Ridge Trail.

  • Heading down toward Windemere Ranch Middle School, Rolling Hills Trail meanders around the fringes of the Windemere community, often squeezing between bushes and trees in some of its tight sections.

  • A stroll on Rolling Hills Trail reveals an abundance of wild animals, including desert cottontail rabbits, squirrels and red-tailed hawks.

  • Running through the Live Oak community, Sycamore Grove is a 0.6-mile paved trail, bordering San Ramon Sports Park and Live Oak Elementary.

  • A small 0.16-mile auxiliary trail to Tassajara Ridge Trail near the Ramona community leads to a slightly elevated, breathtaking overlook on the expanse of Windemere.

  • Heading toward the Camino Tassajara end of Windemere Parkway, Tassajara Ridge Trail offers a vast swath of greenery and a view of both the downhill Tassajara and Windemere communities.

  • Tassajara Ridge Trail offers unbroken expanses of stunning green, with a distant view of Mt. Diablo and the occasional herd of bumbling black cows. This 3.5-mile trail threads through endlessly rolling hills and runs parallel to Camino Tassajara.

  • Climbing up Hidden Valley Ridge’s asphalt hill is like riding a glass elevator suspended over San Ramon. It is steep and long, offers a fantastic view and connects to Lower Hidden Valley Ridge on one side, Tassajara Ridge on the other.

  • The 1-mile asphalt Windemere Ridge Trail runs from Windemere Ranch Middle School to Live Oak Elementary School.

  • Sunset on Dougherty Valley Ridge Trail is profoundly beautiful both on and off the trail.

  • Lower Hidden Valley Ridge Trail runs parallel to and just above Albion Road, bordering the hills and eventually connecting to Upper Hidden Valley Ridge and Tassajara Ridge.

  • The mostly paved 2.84-mile Alamo Creek Trail that cuts through multiple communities and bypasses Dougherty Valley High School is famously trekked by many students on their daily walk home from school.

  • East Alamo Creek Trail, which connects Live Oak Trail to Alamo Creek Trail at a roundabout near Souyen Park, is an easy, paved walk along the edge of Windemere community's Dougherty Valley High School side.

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Daniel Shen and Eva Shen

Settled within the hilly greens of the East Bay, our delicate suburb of San Ramon offers dozens of luscious trails to residents and visitors alike, meandering all throughout and around the town. Playing home to many of these trails is our Windemere community, nestled between Camino Tassajara and Bollinger Canyon Roads.

Over the past couple months, shelter-in-place has afforded us more time to ourselves, as well as urged us to escape the confinement of our houses more often. With our itching for the outdoors, we’ve been exploring the trails in our backyard on walks, bikes and jogs, and on these adventures we’ve discovered some breathtaking sights worth sharing with our readership.