Hardest and Highest Hill Hikes in the SF Bay Area

What is it about walking to the top of high places? Is it the view? The solid workout? That feeling of accomplishment as we stand on the summit? Or do we climb a mountain simply because, in the famous words of mountaineer George Mallory preparing for his fatal Everest attempt, “it is there.”

We may not have any Mt. Everests in the San Francisco Bay Area, but we’re certainly not deprived of mountains hills to climb, whatever our motivation. They may not be tall, but don’t underestimate them; these challenging Bay Area hikes can be as hard as you make them.

This list is a roundup of the best (hardest, steepest, tallest) hikes or trail runs in the SF Bay Area that take you to the top of high places. I’ve generally chosen the most direct and consistent route, the one with the triangular elevation profile, to maximize the steepness factor.

Wherever reasonable I’ve chosen a loop route, because everyone likes loops better than out-and-backs. But where creating a loop makes the climb less direct or longer in mileage than feasible for intermediate hikers, I’ve chosen out-and-backs. The tough Bay Area hikes in this post are all about getting up and down tall things as directly and efficiently as possible.

In my many years of exploring local trails, I’ve stood on the summit of every one of these Bay Area peaks and I can tell you, the views over the bay, hills, and Pacific Ocean are worth it. I would hike uphill all day (literally) for a moment of peacefully surveying the busy suburban fray from above.

If you’re a backpacker looking for a training hike in the Bay Area, this list is a great place to start. Trail runner looking for hill workouts? Ditto. If they’re too easy, strap on a weighted pack, or do repeats. They may not be full-blown mountains, but we’re pretty lucky to have so many great and challenging trails in the bay area, so let’s make the most of them!

Without further ado, here are seven of the best challenging hill climb hikes in the SF Bay Area.

Windy Hill

Total Distance: 7.4 miles
Net elevation gain: 1350 feet (in 2.8 miles)
Highest point: 1905 feet
Average grade of climb: 482 feet / mile
Location: Peninsula near Portola Valley

This 7.4 mile loop in Windy Hill Open Space Preserve is a steep and sunny fire road climb on the way up, and a wooded singletrack stroll on the way down. Along the way you’ll get increasingly sweeping views of the bay (don’t forget to look behind you). In the spring, enjoy the bright orange poppies and other wildflowers.

Begin from the parking lot on Portola road, which has a restroom and drinking fountain. The lot is large but can still be full on busy days. The bulk of the climbing is done on Spring Ridge Trail, with a short out-and-back to tag the summit before continuing south on Lost Trail and then descending on Hamms Gulch Trail.

On anything but the hottest summer days, consider bringing a light jacket or extra layer, as the hill often lives up to its name. Also keep an eye out for the occasional rattlesnake sunning itself across the trail.

Alternates:

• Shorter: retrace your steps back down from the summit instead of completing the loop (5.6 miles)
• Longer: enlarge the loop by descending on Razorback Ridge Trail instead of Hamms Gulch (9.6 miles)

For more information, see the route description on Hiking Project.

Black Mountain (Rancho San Antonio OSP)

Total Distance: 9.8 miles
Highest Point: 2812 feet
Net elevation gain: 2290 feet (in 4.9 miles)
Average grade of climb: 467 feet / mile
Location: Peninsula near Los Altos

Start from the Rhus Ridge Trailhead at Rancho San Antonio OSP. The parking lot is small and often fills up, so you may need to add another mile to your hike by parking on Moody Road near Foothill College.

The first mile, coming up Rhus Ridge trail, is one of the steepest sections of the whole hike! Don’t worry, it’s not like this the whole way. Once you reach the ridge, you’ll turn right and climb more gradually on shaded singletrack.

Close to the top, things open up again for more steep climbing and excellent views. A bit more steep fire road and you’re at the top! The summit is deceptively flat, with some radio towers nearby, but make sure to wander around and enjoy the views of the bay to the east and the Santa Cruz mountains to the west.

This hike is most commonly done as an out-and-back because that tends to be hard enough already. But if you’re looking for an even bigger challenge, consider extending your route to this 13 mile loop which can be done in either direction.

If you’re a backpacker looking for an overnight hike on the SF Peninsula, you’re in luck, because Black Mountain Backpack Camp (reservations required) is just a short stroll away. It’s possible to link this route up with a longer hike in Monte Bello OSP and even on to the Skyline Trail, which links up with several other OSP’s and even Castle Rock State Park.

Mt. El Sombroso (Sierra Azul OSP)

Total Distance: 12 miles
Highest Point: 3018 feet
Net elevation gain: 2189 feet (in 6 miles)
Average grade of climb: 365 feet / mile
Location: South Bay near Los Gatos

This hike in Sierra Azul OSP starts at Kennedy Trailhead and follows Kennedy and then Woods trails to the summit of Mt. El Sombroso, just over 3000 feet. The entire hike is on fire road which can be steep and sunny, so be prepared with plenty of water and sun protection.

The summit itself is anticlimactic, just some doubletrack veering left under the power lines as the trail continues downhill to the right. But the views over the bay as you climb, and the dramatic rolling ridgeline near the top, make up for it.

Most hikers will retrace their steps the way they came, but to add even more rugged Sierra Azul mileage, consider adding in a loop via Limekiln and Priest Rock trails for a burly 15 mile lollipop.

It’s worth noting that even taller Mt. Umunhum, at 3488 feet, is also in Sierra Azul and has been accessible to the public since 2017. It doesn’t fit well into this list though, because hiking to the top is either impractically long for most folks (14 miles one way) from one of the lower Sierra Azul trailheads, or a shorter and milder hike from the higher trailhead on Mt. Umunhum Road. Still, if you’re a connoisseur of Bay Area hill climbs, it’s worth adding to your list.

Montara Mountain via North Peak Access Road

Total Distance: 7.3 miles
Highest Point: 1865 feet
Net elevation gain: 1805 feet (in 3.7 miles)
Average grade of climb: 488 feet / mile
Location: Highway 1 near Pacifica

Montara Mountain’s North Peak summit is a fantastic sea to summit hike with Pacific Ocean views. Starting from the town of Montara on Highway 1 south of Pacifica, you’ll climb the steep, shadeless dirt North Peak Access Road as it winds its way to the summit and views all the way to San Francisco.

From the top, retrace your steps back down or try the even steeper Alta Vista Trail. If you’re looking for the steepest section of climbing around, try hiking up Alta Vista Trail and then cruising down the North Peak Access Road.

Mission Peak

Total Distance: 5.9 miles
Highest Point: 2516 feet
Net elevation gain: 2112 feet (in 2.8 miles)
Average grade of climb: 754 feet / mile
Location: East Bay near Fremont

Good old Mission Peak, near Fremont in the east bay, might be the most classic hill climb hike in the entire Bay Area. This short hike packs a punch with consistent steepness bottom to top, but the views from the top are a worthy reward.

The Stanford Ave. parking lot is notoriously busy, so start early or plan to park on the street and add some distance to your hike. Bring plenty of water and sun protection, because the trail is mostly unshaded. Cows are commonly seen grazing on this route; be sure to say a friendly “mooo” as you pass.

This loop takes you up fire road / two track, across the rocky scramble to the summit, and then down an alternate route with more singletrack. In the winter the singletrack sections can sometimes be muddy and are best avoided after rain so as not to cause further erosion.

Looking for more mileage? You can always descend down the back side of Mission Peak before turning around. Alternatively you can hike from Ed Levin Park to the south for a longer route that tags Monument Peak on the way. And further east, starting in the Sunol Regional Wilderness, you can hike to 3816-foot Rose Peak as a 20 mile out-and-back.

Mount Diablo Summit Loop (North)

Total Distance: 13.7 miles
Highest Point: 3848 feet
Net elevation gain: 3238 feet (in 7 miles)
Average grade of climb: 463 feet / mile
Location: Far East Bay near Concord

Mount Diablo State Park in the east bay is a bit farther away for most bay area residents, but the large and rugged park has enough hike-worthy peaks and tough trails to make it worth the drive.

This loop will take you all the way to the main summit and back down via a series of fire roads and trails. Like many prominent summits in the area, this one has a road to the top, but don’t be put off by those who drove; you got there the hard way.

Mount Diablo State Park is in a class of its own compared to most other parks on this list. Expect tough and rugged trails, and watch out for poison oak and the occasional rattlesnake.

Here’s the full description on Hiking Project, which also lists a lot of other challenging hikes in the area.

Mount Tamalpais

Total Distance: 8.5 miles
Highest Point: 2572 feet
Net elevation gain: 2403 feet (in 4.3 miles)
Average grade of climb: 559 feet / mile
Location: North Bay near Mill Valley

In the north bay, the flanks of Mount Tamalpais (or Mt. Tam, more affectionately) offer dozens of great hikes. For a consistent and direct hill climb to the summit, start from Muir Woods. There’s an entrance fee and parking can be busy, so if you’re not also interested in visiting Muir Woods, consider a less direct (but still challenging and scenic) route from Stinson Beach instead.

Follow a mix of steep fire roads and trails to the summit, which can also be accessed by car, and celebrate having reached it the hard way. Retrace your steps back down for an out-and-back, or branch off onto nearby trails for some variety and more mileage.

Here’s the Hiking Project description for more detail on this and other Mt. Tam hikes.

Bay Area Hiking Tips

If you’re looking for challenging Bay Area hikes, you probably already know what you’re doing, but here are a few important things to keep in mind.

• Bring MORE drinking water than you think you need, especially in the summer. I can’t tell you how many times I have underestimated this and ended up thirsty. Most of these trails are steep and sunny, and unless you’ve researched current conditions in advance, don’t assume water is available during the hike.
• Watch out for poison oak, which often grows alongside (and sometimes into) the trails. Learn what poison oak looks like, and throw a few of these wipes in your pack just in case.
• Keep an eye out for rattlesnakes. Here’s what they look like. They’re usually found sunning themselves across the trail on warm days, or lurking at the edges. If you see one (or any snake for that matter), keep your distance, and proceed carefully around it when there’s enough space.

More Hiking Resources

If you’re into Bay Area hiking, you might also be interested in these:

• Hiking poles: when and how to use them
• Best trail running shoes for hiking, according to thru-hikers
• More hiking and backpacking resources here

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