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Santa Rosa Trail Loop through Box Canyon – Gentler Intermediate

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Santa Rosa Trail Loop through Box Canyon – Gentler Intermediate

Wildwood Park is one of the most versatile local parks there is, with 27 miles of trails skittering through rocky cliffs, cacti-filled desert environs, volcanic rock, riparian forest, and a cool, watery canyon. Wildwood’s archetypal western look served as the set for The Rifleman, Gunsmoke, and Wagon Train back in the day, as well as the movie Spartacus. You’ll be rewarded with beautiful vistas of the Conejo Valley, Santa Rosa Valley and some interesting properties including the train-collector yard.

We’ll start on the Mesa trail and proceed to the Box Canyon. Then, descend down through Box Canyon onto the paved Rocky High Road, the train yard and up the Shooting Star trail to the Santa Rosa trail. We will enjoy the views of Mount Clef Ridge on both sides and head back to our cars.

It is about 6 1/2 miles and approximately 1000+’ of elevation gain.


From the 101 in Thousand Oaks, turn north on Lynn Road and continue 2.6 miles to Avenida De Los Arboles, then turn left. Continue for about a mile to the end and turn into the Wildwood parking lot on the left.

From the 118, travel west to the 23, exit at Avenida De Los Arboles and turn right. Drive further than you remember having to drive to this trailhead (10 or 15 minutes). Turn left into the parking lot when the road ends.

Please review the guidelines (link to the guidelines) to join our hikes.
Restrictions apply for your safety and ours:

  • Don’t show up unless you’re shown on the “Attending” list.
  • Plan on KEEPING UP with the group and completing the entire hike at a moderate pace, or please find an alternative hike that better suits your hiking level.
  • No “Plus Ones” or dogs on Weekday Trailblazer hikes.

The hike host is a volunteer and not responsible for the group. Safety should be a priority for everyone in the group. Please treat this meet-up as hiking with a group of friends. If you become fatigued and unable to continue the hike, it is expected you will advise the hike host of this and return to our starting point on your own. If you are able to proceed, it is expected that you will maintain line of sight with other members of the group at all times and help to promote the group’s safety and fitness goals.
Outdoor sports and other events we plan can be inherently dangerous and accidents may happen. By participating in any posted event, you are taking responsibility for your own safety and well-being. The Weekday Trailblazers Meetup Group and its organizers are not trained leaders and we do not confirm the qualifications of any of its members to lead or participate in trips. All participants take full responsibility for their own actions.
If you choose to sign up for this or any Weekday Trailblazers Meetup event, you are releasing the Weekday Trailblazers Meetup Group and its organizers from all liability in case of possible injuries. Your personal safety depends on your own judgment and experience.
All participants must be 18 or older, or accompanied by a parent or legal guardian.

June 27 2023


Date: June 27, 2023
Time: 8:30 am - 11:00 am
Hiking Group:
RSVP: Visit Meetup Website


928 W Avenida De Los Arboles

928 W Avenida De Los Arboles
Thousand Oaks,CA91360US

+ Google Map


The Weekday Trailblazers
Website: Visit Organizer Website


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Trail statistics are approximate. For safety purposes always assume they are underestimated. But don’t be disappointed if they are overestimated. Bring more water and snacks than you think you’ll need.

Trail descriptions are based on previous hikes. Current conditions are unknown until arrival. Expect the unexpected and plan accordingly.

The Organizers and members of Hiking With Dean are not professional leaders, guides, or mountaineers. The function of the member or organizer is only to organize the trip. Each person who shows up for a trip/meetup (and their guest or guests) is responsible for his or her own safety. By attending a hike, or any other event organized by this group, you are acknowledging that you and any guests that you bring are aware of the risks, dangers and hazards associated with the activity and freely accept and fully assume all such risks, dangers and hazards, and further agree to release and discharge the Organizers, Members of the Hiking With Dean Meetup Group from and against any and all liability arising from your participation in the group activities per our ASSUMPTION OF RISK AND LIABILITY WAIVER and Section 6.2 of the Terms of Service.