Six Bay Area Hiking Challenges that Make Planning Hikes Easy

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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!

Santa Clara County Parks #PIXINPARKS

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 from an easy half-mile hike to a to a moderate 5.5 mile hike. You can find maps for each trail on the Santa Clara County Parks website.

The Santa Clara County Parks Challenge features hikes at some beautiful parks.

East Bay Regional Park District Trails Challenge

The East Bay Regional Park District has been holding a trail challenge for eight 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 posted to All Trails. To complete the challenge you need to  hike 5 of the 20 trails in the guidebook, or hike 26.2 miles of trails in any of the east bay regional parks. Successful challenge participants are eligible to receive a pin while supplies last. 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.

The East Bay hiking challenge is a great challenge to complete in the spring when the hills are bright green.

Sonoma County Trails Challenge

The Sonoma County trails challenge happens every summer. Each summer, you’re invited to hike, run, bike or ride at least five trails featured in the annual Trails Challenge guidebook and get a Trails Challenge T-shirt when you finish. The downloadable PDF trail book is a great hiking resource! In the booklet you’ll find trail maps, alternate routes, and info for the selected parks (they even note which trails are dog-friendly!). You can download the challenge booklet from the Sonoma County Regional Parks website.

Bay Area Ridge Trail 375-mile Challenge

If you get a thrill 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. As a bonus, the Bay Area Ridge Trail goes through many popular parks like Purisima Creek Redwoods, Mission Peak, Mt. Tam, and San Francisco’s Presidio National Park.

The Bay Area Ridge Trail goes through some of the Bay Area's prettiest parks.

Northern California Six-Pack of Peaks

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 and comes with perks like a private challenger party, swag, and trail guides for the hikes. You can register for the challenge on the Six Pack of Peaks website.

San Francisco Stairway Walks

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 12 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.


Nationwide Hiking Challenges

Hiking challenges aren’t limited to the Bay Area. Many regional parks and trails throughout the U.S. organize their own challenges. The North County Trail has a Hike 100 challenge, the Appalachian Mountain Club has a Four Thousand Footer Club challenge, and the Carolina Mountain Club has a Waterfall Challenge. Check out the local parks in your area to see if they host a challenge. Who knows, you might inspire them to create a challenge if they don’t already have one!

Below are three popular hiking challenges that you can participate in, no matter where you live.


The 52 hike challenge involves going on one hike each week.

52 Hike Challenge

One of the most well-known hiking challenges, the 52 Hike Challenge has six challenges to choose from. Most people participate in the original challenge to hike one trail each week. It’s free to sign up, but if you want some motivational challenge swag you’ll need to pay. If you want to take your challenge to the next level check out some of their other challenges like the National Parks Series, Pet Series, Explorer Series, or Adventure Series.

The 365-mile challenge is a hiking challenge where you walk one mile each day.

365 Mile Challenge

Want to hike one-mile each day? Then, the 365-mile challenge is for you! While other challenges often have a free component, this challenge requires participants to register and pay at least $25 before accessing the challenge materials. While I haven’t registered for the challenge myself, the progress tracking sheet shown on their website appears to be designed to track your progress each day. This is a great challenge if you are trying to make hiking a daily habit.

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Don't forget your hiking essentials

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.

Like all outdoor pursuits, hiking can be dangerous. It is up to you to assess your fitness level and education yourself about any potential dangers. While I try to regularly update these hiking guides, you should always research trail conditions before heading out.

Being prepared means arriving at the trailhead with water and some basic provisions. Each and every time I hit the trail I bring a backpack with more water than I think I need, a small first aid kit, and a snack. I also share my itinerary and plans with friends or family and I carry an InReach so I can summon help if needed. If you want to know what I carry in my pack during day hikes check out my blog post about essential gear for day hikers.

Stay safe, enjoy the trail, and soak up the magic of nature! What challenges will you do this year?

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