a-oakay

by
par
Jesse Boudart
No items found.

Bay Area

23

mi

km

Distance

distance

50

%

Time Spent Off-Road

temps dépensé sur saleté

2.5

hrs

Estimated Total Time

estimé temps total

3

Estimated Dismounts

estimé démonter

42mm

Suggested Tire Size

conseillé pneu de largeur

Novice

Easy

Intermediate

Hard

Extreme

débutant

facile

intermédiaire

dur

extrême

Difficulty

difficulté

a-oakay

by
par
Jesse Boudart
No items found.

Distance

Distance

23

mi

Time Off-Road

temps dépensé sur saleté

50

%

Estimated Time

estimé temps total

2.5

hrs

Estimated Dismounts

estimé démonter

3

Suggested Tire Size

conseillé pneu de largeur

42mm

Difficulty

difficulté

Easy

description

la description

Traversing the East Bay Hills among the oak and redwood trees

Load up on coffee, blast up Tunnel Road, slither on Skyline Blvd., then stick your hands in the dirt at Westridge Trail via Skyline Staging Area. 

Follow the flowy slightly uphill path on the side of the mountain. Eventually, you’ll top out at the Redwood Bowl. Take a sip of water, and then start your first fun descent. 

You’ll slide down Graham Trail, which transitions to Dunn Trail, and then if you haven’t blown all the turns because you are having so much fun, keep going downhill on Monteiro Trail. Take a rest, and then you’ll start pedaling up Redwood Road to the next dirt segment.

You’ll pedal uphill on Dunn Trail, which will snake up until a point that will converge back onto a paved Skyline Rd. Continue up to a crest, and then prepare for another excellent descent.

Big Trees Trail is borderline mountain biking, but it’s just smooth enough on gravel tires. Enjoy the send! The path will take you to another larger field and a trail aptly called Sunset Trail, which will take you out of Joaquin Miller Park and back on your descent (lightning speed) down to Oakland and to your ending restaurant.

published -
8/20/25
  • Classic East Bay Dirt Trails
  • Fun and pleasant downhill descents
  • Oak & Redwood trees abound

  • The trails are also popular with hikers and can be crowded on the weekends
  • This is a climby route, but the road climbs are gentle

  • Redwood Bowls
  • Sunset Trails

Plenty of water on the route

Dusty, woodsy
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highlights-chevron

highlights

  • Classic East Bay Dirt Trails
  • Fun and pleasant downhill descents
  • Oak & Redwood trees abound

highlights-chevron

what to know

  • The trails are also popular with hikers and can be crowded on the weekends
  • This is a climby route, but the road climbs are gentle

highlights-chevron

points of interest

  • Redwood Bowls
  • Sunset Trails

highlights-chevron

food / hydration

Plenty of water on the route

highlights-chevron

terrain

Dusty, woodsy

route map

la plan de route

photos

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