Six Bay Area Hiking Challenges that Make Planning Hikes Easy

These six San Francisco Bay Area hiking challenges make it easy for you to accomplish your hiking goals.

If you’re anything like me, you start the year full of enthusiasm, ready to kick butt and slay some goals. But, by mid-January you’ve run out of steam because you haven’t been able to check anything off of your list, and you just want to chuck all those goals out the window. Who’s with me?!

If this sounds familiar, you need to check out these six hiking challenges that make it easy to succeed. I love these challenges because they remove the planning overwhelmed by providing maps and routes, and most of them have a handy checklist so you can see your progress in action. The only thing you need to do is choose your challenge and hit the trail!

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Santa Clara County Park’s Magnificent Seven challenge encourages you to hike seven trails and share your hike on Instagram. Hikers who complete the challenge can receive a free t-shirt or bandana. The trails in this challenge range in distance from 2 miles to 6.7 miles. You can find maps for each trail on the Santa Clara County Parks website.


The East Bay Regional Park District has been holding a trail challenge for seven years in a row. This year they’ve made entering the challenge super easy. To participate you can download a PDF guidebook, pick-up a printed guide at one of their visitors centers, or find all 20 trails grouped together in All Trails. You don’t need to register for the challenge and you can even pick-up your free hiking challenge t-shirt before completing the challenge. If you are new to hiking or don’t want to complete this challenge on your own you can join one of the park’s group hikes led by trained naturalists.


Sonoma County didn’t update their hiking challenge for 2019, but since I didn’t get around to participating in the challenge last year I’m adding this one to the list. While you won’t get a prize for participating, the downloadable PDF trail book is a prize in and of itself. In the 40-page booklet you’ll find trail maps, alternate routes, and info on 15 parks (they even note which trails are dog-friendly!). You can download the 2018 challenge booklet from the Sonoma County Regional Parks website.


If you get a trill out of checking big goals off of your list, this unofficial challenge is for you. While the full loop isn’t yet complete, the Bay Area Ridge Trail has 375 miles of multi-use trails in the North Bay, South Bay, East Bay, San Francisco, and on the Peninsula. You can plan your own route to complete the 375-mile trail or you can use the free downloadable trail maps on the website and hike the trail in 65 small sections.


The Six-Pack of Peaks challenge is for experienced hikers who want to tackle the six most challenging peaks in the Bay Area. The peaks in this year’s challenge are Mount Umunhum, Mount Saint Helena, Mount Tamalpais, Mount Diablo, Mount Sizer, and Rose Peak. While you can do the hikes on your own, the official challenge costs $30-$75. You can register for the challenge on the Six Pack of Peaks website.


While not an official challenge, this is the perfect goal for San Francisco residents who find it difficult to leave the city. The hills and stairways make San Francisco the perfect city for urban hiking and these hills and stairways will definitely get your heart pumping. Amy and James of the Doing Miles blog have mapped 11 stairway walks that range from 8-13 miles in distance. The routes cover all of San Francisco and a bit of Marin. To make navigating the routes easy you can download the gpx files for each route and load it into Gaia GPS. You can check out all of the routes on the Doing Miles website.

If you’re new to hiking check out my post on the 10 inexpensive and essential items I always carry with me on day hikes. What challenge are you going to do this year?

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