Contra Costa

Jackass Canyon Bootleg


During Prohibition (1920s and 1930s) Ranchers set up distilleries hidden in the Mount Diablo region to supplement their hand-to-mouth existence. Help the ranchers in their elicit enterprise and move some hooch out of Jackass Canyon.
11 MI
Insertion Point: Finley Road, Clayton, CA

Map of Jackass Canyon Bootleg
Google Map


It’s the 1920’s and Prohibition is in full swing across the United States. Moonshiners have sprung up throughout the ranches and farms in California. A remote canyon on the east side of Mount Diablo has developed a reputation for “jackass” whiskey – and the canyon itself soon adopts the namesake. It’s become a hive of moonshiners and drawn the attention of the Prohis, Federal Prohibition agents. The moonshiners have tapped the Tassajara Creek that runs through the Canyon floor, using spring boxes to distill the hooch. To protect the operation, armed sentries stand watch from the cave marked cliffs of the Black Hills that overlook the canyon.


Your circuit begins at the entrance to Old Finely Road among the ranches that use the parkland for cattle grazing. Head west on Old Finely Road. (map)

Abandoned Ranchland Home

Continue along Old Finely Road until you reach a modest abandoned structure. The ranchers often use this area for cattle grazing and it marks an important fork in the road. Here you will leave Old Finely Road and proceed west onto Oyster Pt Trail. Immediately, look for a small unmarked single track that leaves the main trail and follow it through a short grove until it intersects with Jackass Canyon Trail.

Illicit Zone

Follow Jackass Canyon Trail into the canyon itself until you reach the End of Trail maker. From here, you’ve entered the illicit zone. The maintained trail fragments into animal trails, which in turn dissolve into brush and, in some parts, bushwhacking. Moonshiners, Prohis, and marksmen lurk amid the canyon so proceed with care.

Tassajara Creek

Drop deep into the Canyon to visit the sites of stills and springboxes that feed on Tassajara Creek.

Black Hills Ridge Line

Ascend to the craggy ridge line that overlooks the canyon. Here you will fine pock marked sandstone that offers many hiding places for the armed sentries to use when guarding the cottage industry below.

Cave Point

Scramble along just beneath the ridge line until you reach the ridge’s zenith: Cave Point. From here, continue your bushwhack until you reach the main road.

Exit the Illicit Zone

You’re out of the canyon and you can move quickly on the maintained fire road. But, you’re also vulnerable. Move fast until you reach the main gate, beyond which is official parkland.

Oyster Point

After several miles on the fire road you will hit a juncture. Leading to the west is Oyster Point trail, which will return you to the insertion point. But, the Prohis are getting close. A few miles down Oyster Point trail break off and head up to Oyster Point itself. From here you have a view of the entire region and you can hide out briefly while the Heat passes. Once the coast is clear, use Oyster Point Trail to return to the insertion point at Finely Road.


It’s time to enjoy a bit of that Jackass. Saint George Spirits in Alameda specializes in craft spirits and has a few whiskeys in its lineup. Stop by for a cocktail or keep it authentic and enjoy it neat.

Breaking & Entering Bourbon
St George Spirits is an artisan distillery in Alameda


Mt. Hamilton Patrol


Nocturnal astronomers-in-training reside and work at Mt. Hamilton observatory.  Ride from Livermore up 4000 FT to their monastery in the stars.  After checking up on the young star gazers continue though the outer banks of the bay area and back into Livermore.


  • Mt. Hamilton Observatory
  • The Junction
  • Livermore Wine District