About this Site

Hikingwithdean.com is the brainchild of Dean, the founder and organizer of the Meetup hiking group Hiking With Dean. Here you will find past and upcoming Meetup group hikes from all over southern California by Meetup groups hand-picked by yours truly.  Don’t see your favorite group? Drop us a line and ask us to add it. [Note: This site uses the Meetup API but is not verified by Meetup.]

About Hiking With Dean

Hiking With Dean is the largest and most popular Meetup hiking group in the country and 2nd largest in the world (after Hong Kong Hiking Meetup)*. HWD’s hikes are based upon a simple philosophy: You should be able go out your front door and within a few minutes be on trails winding your way through the local wilderness. Thus, most of HWD’s hikes are found in the Santa Monica Mountains, Santa Susana Mountains, Simi Hills and Conejo Valley. All hikes are free

We are not a beginner hiking group, but I do schedule beginner hikes sometimes and some hikes do have a beginner option. Be sure to read the hike descriptions and ask questions if you have any. Most of our hikes are moderate to strenuous. Because of my own limitations we’ll refrain from any serious rock climbing and avoid precarious ledges and ridges. But we do avoid fire roads when we can.

Our hiking group is different from the others. Instead of looking through just hiking books for a hike, I look through my collection of old maps and aerials for forgotten ranch roads and trails that I can add to the book hikes. Once upon a time our “open space” was home to ranchers, farmers, movie sets, homesteaders, and other characters that have left behind their marks for us to discover and uncover.

*HWD has the largest membership per leader

HWD Group Rules

  • Don’t be a flake by signing up and not showing up
  • No dogs unless indicated in hike description (our special dog-friendly hikes)
  • By joining you agree to the Assumption of Risk and Liability Waiver

Donations Accepted – VIP Club

As a HWD donor you are invited on special appreciation hikes known as VIP Hikes. Enjoy many benefits not available to other members or groups, for example, breakfast at the trail head, free prizes and other goodies, hiking secret and forbidden trails, no waiting lists, etc. Sounds better than the usual “please donate” doesn’t it? For more information please visit the V.I.P. Circle page.


Your donation is a recurring subscription and will automatically renew until you cancel. You must cancel your subscription before it renews to avoid the billing of the next subscription term’s fees to your account. No refunds are given for partial term cancellations. If you cancel a subscription before the subscription period ends, your subscription (and your access to its content) will continue until the subscription period ends (it will not automatically renew in this case). Exceptions to no-refund policy are considered on a case-by-case basis.

Proud Member of:

Santa Monica Mountains Trails Council
California State Parks Foundation
The Mountains Restoration Trust
Montecito Trails Foundation
Conejo Open Space Foundation

A Few Testimonials

Dean is a wonderful leader. He really paid attention to the needs of the group. He facilitated the group, but didn’t control the group. I will attend again — Kimmy

If Dean [one of the original SoCal Meetup-ers mind you] would ever write a book on hiking SoCal [as he rightfully should] it would be a must-buy. Dean is both knowledgeable and adventurous. Conscientious and kind. I would have no problem hiking with Dean anywhere. – Les

Dean is a great hike leader. He knows the trails. — Lydia

The group leader Dean is very conscious of all of us hikers as a group. We all get to trek at our own pace comfortably and still stay together.He’s got an agenda planned with an extra twist on where we are going to hike. — elyse

Dean is an excellent group leader who knows the trails very well. He is always looking out for the welfare of his hikers. The group attracts some of the most pleasant people you can hope to meet. — Bruce

What can I say? This group ROCKS!!! Some of the friendliest people I have met and the Organizer, Dean is a sweetheart! – Sara

Dean has organized the best group of hikers who like to hike and have fun. — Blake

Dean is extremely knowledgeable and serves up a seemingly endless array of hikes. A very pleasant and down-to-earth group of people who are easy to get to know … and like — Drew

Dean is a strong hike leader with a friendly and outgoing group of people who know how to have fun while hiking – Laura