Ruby Hill Country Club

Another first-class country club, this time in the wine country in eastern Pleasanton. It is in a gated community.

Listing from Wikivoyage: Pleasanton, CC BY-SA 4.0.

Updated 28 Sept 2026. Something wrong? Tell us.

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Ruby Hill Winery
Beautiful, upscale winery in the east of Pleasanton. The area immediately surrounding the winery is much like that of Napa and Livermore Wine Country, and is backed by vineyards and mansions. Near the winery is the (also upscale) Ruby Hill gated community.
Drink
Rubino Estates Winery
In size and grandeur, it has some similarities with Ruby Hill Winery. Rubino Winery has a long entrance driveway that leads away from Vineyard Avenue to the winery.
Do
Shadow Cliffs
The park was once part of the quarry, but the excavated land is now Shadow Cliffs Lake. It includes a couple miles of trails around the lake and a popular lakeside beach. However, be prepared for the strong barbecue odors encountered around the grills near the lake.
Do
Callippe Preserve
Callippe Golf Course
Callippe Preserve is known to most Pleasantonians as a golf course; however, there is a nearly 4-mile (6-km) trail around the golf course and local ranching areas. The trail can get muddy in winter, though, and is not easy to find. But it does give those from outside of Pleasanton an idea of the local flora and countryside in general.
Trail is free