Bollinger Canyon Road Is Doing All of Windemere's Work This Fall

Ask a Windemere resident how their Thursday night looks in September and most describe two separate outings: a walk somewhere up near the middle school, then a drive across the neighborhood later for food trucks and local art. Two errands, two trips, two parking spots. Check the addresses on both and they sit on the same street.

Bollinger Canyon Road runs from the trailhead behind Windemere Ranch Middle School, past the Dougherty Station library and arts center, and down to the restaurant floor at City Center Bishop Ranch. The ridge walk, the last two Third Thursday markets of the year, and the new Turkish jazz club that just opened this spring all sit on one road. Most people are still treating it as three separate destinations.

The Trail Starts Behind the Middle School

The Rolling Hills Trail begins on Bollinger Canyon Road directly behind Windemere Ranch Middle School. From there it runs southeast past Six Pillars Park toward the Tassajara Ridge Trail, an easy 3.8-mile out-and-back that takes most walkers about an hour and a half to two hours. The terrain alternates between paved sections and packed dirt, with enough elevation change to feel like a real walk without requiring hiking boots. Cattle graze along parts of the route depending on the season, and jackrabbits are common enough that regulars stop mentioning them.

Six Pillars Park itself sits at 12219 Windemere Parkway on 2.74 acres, and its name is not decorative. The park honors the six traits at the center of the San Ramon Police Department's Character Counts program: trustworthiness, respect, responsibility, fairness, caring, and citizenship. Beyond the civic naming, it functions as a genuine trailhead with a small skate and scooter area, a playground built more for kids seven and up than toddlers, and parking that connects straight into the Rolling Hills route.

Push further along the ridge and the Tassajara Ridge Trail picks up at two access points: the Tassajara Ridge Staging Area off Windemere Parkway, and a second trailhead on Longleaf Circle. On a clear day the overlook here reaches past San Ramon and Dublin toward Danville, with Mount Diablo visible on the horizon. None of this requires a special trip. It starts on the same road most residents already drive twice a week.

A few practicals worth knowing before you go:

• Rolling Hills Trail: 3.8 miles round trip, easy to moderate, paved and dirt surface, dogs welcome on leash
• Six Pillars Park: 2.74 acres, parking on site, best for kids seven and older
• Tassajara Ridge Trail: access from Windemere Parkway or Longleaf Circle, best views on clear days

The Same Street Leads to the Library

Follow Bollinger Canyon Road away from the trailhead and it arrives at the Dougherty Station complex, where the library sits at 17017 Bollinger Canyon Road and the Community Arts Center sits next door at 17011. Both share a parking lot with the Diablo Valley College San Ramon campus, which is why the library's programming reads less like a quiet reading room and more like a community hub. The fall calendar is already filling in: a Verses & Voices poetry workshop led by the city's Poet Laureate, Jaz Sufi, is scheduled for September 2, and a Speak Up! English Language Conversation Group meets the following Friday for adult ESL learners.

The bigger draw sits just outside those doors. Third Thursday Arts & Eats launched this May as the city's first monthly art market and food truck series, running from 5 to 9 p.m. on the third Thursday of each month through October. The format has stayed consistent since the May 21 debut: about ten local artists selling original work and handmade goods, eight rotating food trucks, live acoustic music, and community booths from partners including the library and the DVC campus next door.

October 15 closes out the series until it presumably picks back up next May, which makes these final two Thursdays worth marking rather than treating as a given. The city's Recreation Supervisor, Adam Chow, described the goal when the series launched as "an exciting opportunity to bring the community together in a creative and engaging way." Six months in, that's mostly what it has been: a low-key, family-friendly stop that doesn't require driving anywhere near the freeway.

Keep Going and the Street Turns Into a Restaurant Row

Bollinger Canyon Road doesn't stop at Dougherty Station. Follow it further and it becomes the address for City Center Bishop Ranch, where the last twelve months have brought some of the more serious dining additions San Ramon has seen. KHAKI Indian Bar and Canteen opened on the second floor in summer 2025, led by chefs Sujan and Pujan Sarkar, both of whom carry Michelin recognition from prior restaurants. It reworks Indian comfort food using regional techniques rather than the pan-Indian menu most East Bay Indian spots default to.

Meyhouse arrived this spring after more than a year of anticipation, opening April 30 in the roughly 5,200-square-foot space that used to be Dumpling Time. It's a Turkish restaurant and jazz club, the first East Bay location for a concept that started in Palo Alto and Sunnyvale, and the jazz component started the following week on May 8 with Brazilian jazz-samba artist Larissa Viana, followed later that month by eleven-time Grammy winner Tony Lindsay. The menu runs on meze-style small plates and mesquite-grilled entrees, with a wine list that pulls from Turkey, Armenia, and Georgia rather than the usual Napa-heavy list.

Rico Rico Taco, an Oakland taqueria known for handmade tortillas and spit-roasted al pastor, filled a first-floor space between West Elm and Fieldwork Brewing Company in February. And every Saturday morning, the same corridor hosts the San Ramon Farmers Market at Alexander Square, now in its 19th season with more than 70 growers and food producers.

None of this requires a special trip across town. It's the same road as the trailhead and the arts market, just a few more minutes down it.

The Whole Corridor, One Trip

The habit worth breaking this fall isn't the walk or the market or the new restaurant. It's treating them as three separate reasons to get in the car. Windemere residents already drive Bollinger Canyon Road more than any other street in the neighborhood. The ridge trail sits at one end of it, the last two Third Thursday markets of the year sit in the middle, and a Michelin-adjacent kitchen and a Turkish jazz club sit at the other. September 17 and October 15 are the last chances this year to string all three together on the same trip before the market goes quiet until spring.

For more on what's happening across Windemere and the rest of the San Ramon Valley, Scott Thompson covers the neighborhoods he works in with the same attention to detail, whether that's a new restaurant on Bollinger Canyon Road or a shift in what a listing actually sells for a few blocks away.