Hard Hikes Near Palo Alto

The hills around Palo Alto look gentle from El Camino Real. They are not. Black Mountain rises to about 2,800 feet behind Los Altos. Mount Umunhum tops 3,400 feet. The canyons on the coast side of Skyline Boulevard drop far below the ridge, so every loop that starts up top ends with a long climb out.

This guide picks nine hard hikes within about an hour of town. Distances and climbs come from the managing agency where it publishes them. For a few routes we use figures from Peninsula Open Space Trust (POST), the land trust that helped buy many of these preserves. We name the source each time. Where nobody publishes an elevation gain, we say so rather than guess. For gentler options, see our best hikes near Palo Alto.

The hard hikes at a glance

Big climbs close to town

Black Mountain by the Abbors Trail

This is the local test piece. Midpen describes the Stephen E. Abbors Trail, long called the PG&E Trail for the power towers it follows, as a challenging 3.7-mile hike with 1,600 feet of gain. Past it, the Black Mountain Trail continues about four miles in all to the 2,800-foot summit. A good plan is to climb the exposed Abbors Trail while you are fresh and come down through the shade of Wildcat Canyon.

• Trailhead: Rancho San Antonio, Cristo Rey Drive off Interstate 280. Midpen puts the preserve trailhead beside the 85-car northwest lot.
• Dogs and bikes: no dogs. Bikes on designated trails only and none west of Deer Hollow Farm.
• Parking and fees: free, but the lots fill early. Check live counts before you leave home.
• Best season: cool, clear days from November to April.
• Safety: almost no shade on the power line climb. Midpen asks hikers to report mountain lion sightings at 650-691-2165.

Our Rancho San Antonio trail guide maps the junctions.

Windy Hill Loop

Midpen's signature loop from Portola Road runs 7.2 miles on the Spring Ridge, Lost and Hamms Gulch trails. POST describes a similar loop of 7.5 miles with 1,400 feet of gain and rates it hard. Climb the open grass of Spring Ridge first, take in the bay and the Pacific from the summit and descend through the woods of Hamms Gulch.

• Dogs and bikes: leashed dogs on the named loop trails, including Spring Ridge and Hamms Gulch. Bikes on designated trails only.
• Parking and fees: lower lot on Portola Road, 47 spaces plus 2 accessible. Overflow at Portola Valley Town Center. No fee.
• Best season: fall for clear views, spring for flowers.
• Safety: Spring Ridge is long and exposed. Midpen closed the connector between the Hamms Gulch and Eagle trails November 3 to 6, 2026 for bridge repairs.

See our Windy Hill guide for parking details.

Summits to the east and south

Mission Peak

The sharp summit above Fremont is the most crowded hard hike in the region. The East Bay Regional Park District calls it a 3-plus-mile hike to the top and says about five hours are needed to reach the summit and return. It does not publish an elevation gain. The summit stands at about 2,520 feet and the upper mountain is open grass with almost no shade.

• Trailhead: the district recommends Ohlone College, 43600 Mission Blvd., for a longer but more gradual climb. The Stanford Avenue staging area is steeper and very congested.
• Dogs and bikes: dogs must be leashed in developed areas and near trailheads. Bikes on wide multi-use trails marked on the map.
• Parking and fees: $4 at Ohlone College. Stanford Avenue is free, but Fremont restricts street parking on weekends.
• Best season: winter and early spring.
• Safety: hours are strictly enforced with citations of at least $300. The district says several dogs die of heat stroke here every year.

Check the district's Mission Peak page for alerts. Our Mission Peak guide covers hours and the drive.

Mount Umunhum Trail

Midpen describes this trail as 3.9 miles from the Bald Mountain parking area to the 3,486-foot summit, through chaparral and knobcone pine past rocky outcrops. That makes about 7.8 miles round trip with steady climbing the whole way up. Midpen does not publish the total gain. At the top it is the highest point on the Bay Area Ridge Trail.

• Dogs and bikes: no dogs anywhere in the Mount Umunhum area, even inside a car. Bikes and horses may ride to the Trailhead Shelter about 3.5 miles up.
• Parking and fees: Bald Mountain lot, 23 spaces plus 1 accessible and 4 roadside. Free. Open 7 a.m. to half an hour after sunset; the entrance gate closes at sunset.
• Best season: clear days after winter storms, when views reach the Sierra.
• Safety: hot, steep chaparral with little shade. Start early in summer.

Our Sierra Azul guide covers the summit history.

China Hole Loop, Henry W. Coe State Park

Coe is the wild card: about 87,000 acres of steep ridges east of Morgan Hill. The volunteer coepark.net site describes the China Hole Loop from the Coe Ranch trailhead as 10 miles with 1,400 feet of gain. It drops on the Madrone Soda Springs Trail, then follows the creek with 12 crossings to China Hole and climbs back out.

• Dogs and bikes: dogs only in the Coe Ranch campground, on paved areas and on the half-mile Live Oak Trail. Bikes are allowed on many fire roads; ask about e-bikes.
• Parking and fees: $8 per vehicle. The last 10 miles of road take about 30 minutes, State Parks says.
• Best season: spring, when the creeks run and the hills are green.
• Safety: summer heat is severe. The descent is steep and slippery in places.

See our Henry W. Coe guide.

The coast side of Skyline

Purisima Creek, Harkins Ridge and Whittemore Gulch

POST describes a 9.3-mile loop on the Purisima Creek, Craig Britton, Harkins Ridge, North Ridge and Whittemore Gulch trails, with 2,132 feet of elevation change. It rates the route hard and allows 5 to 7 hours. You climb from the creek through second-growth redwoods to ridge views over the coast, then drop steeply back down Whittemore Gulch.

• Trailhead: the coast-side lot southeast of Half Moon Bay, which Midpen lists with 7 spaces plus 1 accessible.
• Dogs and bikes: no dogs. Bikes on designated trails. Midpen's map shows Whittemore Gulch closing seasonally to bikes and horses.
• Parking and fees: free, but tiny. Midpen strictly enforces no-parking zones, so arrive early.
• Best season: fall for clear ocean views. Expect mud after rain.
• Safety: cell service is sporadic in the canyon. Carry water, since none is available on the trails.

Our Purisima Creek Redwoods guide compares the entrances.

El Corte de Madera Creek loop

POST describes an 8.8-mile loop from Skeggs Point with 2,100 feet of gain and rates it hard, 5 to 6 hours. It links the Tafoni, Fir, Methuselah, Giant Salamander, Timberview and Manzanita trails. Highlights include the honeycombed sandstone at the Tafoni observation deck and an old-growth redwood about 50 feet around at its base.

• Dogs and bikes: no dogs. This is the busiest mountain bike preserve on the Peninsula, so listen for riders on single track.
• Parking and fees: Skeggs Point is a Caltrans lot with 26 spaces. Drivers coming from the north may not turn left into it. No fee.
• Best season: summer, when the dense forest stays cool.
• Safety: cross Skyline with care. The trail web is dense, so carry Midpen's map.

See our El Corte de Madera guide.

State park long days

Castle Rock: Ridge and Trail Camp Loop

State Parks lists this loop from the Kirkwood lot at 5.15 miles with 1,190 feet of gain. It loops through the park's sandstone ridge country and past the trail camp, with outcrops such as Goat Rock looking out toward the Pacific. For a bigger day, the Middle of the Park from the Gap Loop runs 9 miles with 1,530 feet of gain from Saratoga Gap.

• Dogs and bikes: dogs prohibited throughout the park. Bikes only on the Skyline Trail north of Highway 35 and the campground service road.
• Parking and fees: $10 per vehicle, $9 for seniors. Day use 6 a.m. to sunset.
• Best season: fall for clear air and black oak color.
• Safety: no cell reception in or near the park.

Check the State Parks page for status. Our Castle Rock guide covers climbing closures after rain.

Peters Creek Loop, Portola Redwoods

The longest hike here reaches one of the most remote old-growth groves in the region. From the Old Tree trailhead, State Parks routes you 2.5 miles on the Slate Creek Trail to the trail camp, about 2.5 miles more on the Bear Creek Trail, around the Peters Creek Grove and back: 11.9 miles with 1,030 feet of elevation change.

• Dogs and bikes: hikers only on all trails. Dogs only in campsites, picnic areas, paved roads and the Escape Roads loop.
• Parking and fees: $10 per vehicle, $9 for seniors. Day use 6 a.m. to sunset.
• Best season: late spring and fall. Expect mud and fallen trees for days after winter storms.
• Safety: no cell service, no gas and no store nearby. Carry a light in case you finish late.

Our Portola Redwoods guide covers the drive.

Safety for big days

If you want a shorter but steep option close to town, the full Los Trancos Trail loop at Foothills Nature Preserve runs roughly 7 to 8 miles, with about 1,000 feet of climbing on the 5-mile shortcut. No transit reaches any of these trailheads, so you can compare rental cars if you are visiting without one.

Frequently asked questions