Hiking the Peninsula & Santa Cruz Mountains

The Mid-Peninsula is one of the best hiking regions in the Bay Area. Thousands of acres of open space preserves, redwood forests, and coastal ridgelines sit within a 30-minute drive of our West Menlo Park property. Thanks to decades of land conservation by the Midpeninsula Regional Open Space District, you can walk from rolling grasslands into old-growth redwood forest and emerge on a ridgeline overlooking the Pacific — all before lunch.

The 10 hikes in this guide are organized by difficulty, from flat family strolls to challenging all-day treks. Every hike listed is free or under $6, and we include the details that matter most to visitors: drive times, dog rules, parking reality, and what makes each trail worth your time.

Flat to gentle grades. Great for families, casual walkers, and visitors wanting scenery without a serious workout.

1. The Stanford Dish

3.7 mi loop · ~530 ft gain · 1–1.5 hrs · 5 min from property
Trailhead: Stanford Ave. at Junipero Serra Blvd. · Free · Sunrise to sunset (hours vary by season)
Dogs: No · Bikes: No

The most popular walk in the area and a local institution. A paved loop through Stanford's foothills with panoramic views of the Bay, the campus, and the iconic 150-foot radio telescope. Well-maintained and popular with runners, walkers, and locals getting their morning workout. The one real hill is at the start; the rest is gentle rolling terrain. No shade anywhere — bring sunscreen, hat, and water. Watch for wild turkeys, ground squirrels, and the occasional rattlesnake in warm months.

2. Pearson-Arastradero Preserve

1.5–4+ mi loops · 100–400 ft gain · 45 min–2 hrs · 10 min from property
Trailhead: 1530 Arastradero Rd., Palo Alto · Free · Sunrise to sunset
Dogs: Yes, on leash · Bikes: Designated trails only

A 622-acre network of rolling hills, open meadows, and small creeks. Trails weave through grasslands and oak woodlands with gentle grades suitable for all fitness levels. The Juan Bautista de Anza and Meadowlark trails make a popular 2.5-mile loop. A small lake (Arastradero Lake) adds scenic variety. Spring wildflowers are spectacular (March–May). Connects to Foothills Nature Preserve via the Bay-to-Ridge Trail for a longer hike. Very family-friendly — good for young children and strollers on the main paths.

3. Rancho San Antonio — Deer Hollow Farm Loop

2.8 mi loop · ~250 ft gain · 1–1.5 hrs · 20 min from property
Trailhead: 22500 Cristo Rey Dr., Cupertino · Free · 8 a.m. to 30 min after sunset
Dogs: No (entire park) · Bikes: No

Arguably the most popular trail system in the Bay Area. The easy Deer Hollow Farm loop is a flat, scenic walk through oak woodland to a working farm with cows, pigs, goats, sheep, chickens, an organic garden, and the restored 1800s Grant Cabin. Perfect for families with kids. Over 25 miles of trails in the combined preserve for those wanting more (see Moderate Hikes below for extended options).

Noticeable elevation gain, 2–4+ hours. Good workout with rewarding views.

4. Windy Hill Open Space Preserve

Up to 6.5 mi loop · ~1,400 ft gain · 3–4 hrs (full loop) · 15–25 min from property
Lower trailhead: Portola Road, Portola Valley (47 spaces) · Upper: Skyline Blvd. pullouts
Free · Half-hour before sunrise to half-hour after sunset
Dogs: Yes, on leash (designated trails including Hamms Gulch) · Bikes: Designated trails

One of the best hikes on the Peninsula. The 1,335-acre preserve features a dramatic mix of open ridgelines, oak woodlands, redwood groves, and grassy meadows. From the summit, on clear days you can see San Francisco, Mt. Diablo, Mt. Hamilton, Mt. Tamalpais, and the Pacific Ocean.

Trail options: The full Spring Ridge/Hamms Gulch loop (6.5 mi, best done clockwise) traverses all the habitat types and packs 1,400 ft of gain. For something shorter, the Anniversary Trail from Skyline (2–3 mi out-and-back) is an easy ridgeline walk with views. The Sausal Pond loop (1.5 mi) from lower parking is good for dogs and quick walks.

5. Foothills Nature Preserve

Up to 15 mi of trails; popular loops 2–6 mi · 15 min from property
Address: 11799 Page Mill Rd., Los Altos Hills · Sunrise to sunset
Admission: $6 for non-Palo Alto residents (free weekdays for all, free for PA residents). Visitor cap of 400–600 people.
Dogs: Weekdays only, on leash. NOT allowed weekends or holidays. · Bikes: Paved roads only

A 1,400-acre gem in the eastern foothills of the Santa Cruz Mountains. Once restricted to Palo Alto residents only for over 50 years, it finally opened to the public in December 2020. Three distinct habitats — chaparral, oak woodland, and grasslands — with Boronda Lake (10 acres, stocked for fishing, great for kids), Vista Hill for panoramic Bay views, shaded picnic areas under old oaks and fruit trees, and even a tent campground (May–October, 8 sites).

6. Rancho San Antonio — Extended Loops

5–16 mi · 600–2,400 ft gain · 2–6 hrs · 20 min from property
Same trailhead and parking as Deer Hollow Farm (#3 above)

Most visitors turn around at the farm, but the preserve extends deep into the Santa Cruz Mountains foothills. The Wildcat Canyon loop (5–6 mi, 600–800 ft gain) passes beautiful creek crossings and small waterfalls in winter. The PG&E Trail loop (7–9 mi, 1,600 ft gain) is the classic locals' workout with expanding views from open chaparral. The Black Mountain summit (10–16 mi, 2,400 ft gain) climbs to 2,800 feet for sweeping views of Stevens Creek Canyon and all of Santa Clara Valley — a serious all-day effort.

7. Coal Creek Open Space Preserve

3–5 mi loops · 300–600 ft gain · 1.5–2.5 hrs · 20–25 min from property
Parking: Small lot off Skyline Blvd. · Free · Half-hour before sunrise to half-hour after sunset
Dogs: Yes, on leash · Bikes: Designated trails

The "secret" local recommendation for people wanting fewer crowds. A less-visited preserve off Skyline Boulevard with fire roads and single-track paths through forested canyons. The Meadow Trail and Crazy Pete's Road make a reliable loop. Trails stay shaded longer than other preserves, making it a good warm-weather choice. Some uneven ground — wear proper hiking shoes. Connects to Russian Ridge for a longer outing.

Significant elevation, distance, or rugged terrain. For experienced hikers looking for a real adventure.

8. Huddart Park

2–6+ mi loops · 400–1,000+ ft gain · 1.5–4 hrs · 20 min from property
Address: 1100 Kings Mountain Rd., Woodside · 8 a.m. to sunset
Admission: $6 parking fee
Dogs: Yes, on leash · Bikes: Designated trails

Shaded trails through redwood groves, Douglas fir, and oak woodland. The Crystal Springs Trail and Dean Trail offer steady climbing through beautiful forest that feels worlds away from Silicon Valley. Fern-lined creeks and lush forest floor in winter and spring. Connects to longer ridge trails for all-day hikes. The $6 fee keeps it consistently less crowded than the free preserves — one of the best reasons to come here. Also a solid trail running destination.

9. El Corte de Madera Creek Open Space Preserve

3–12 mi loops · 500–2,000+ ft gain · 30 min from property
Parking: Skeggs Point lot on Skyline Blvd. (limited spaces) · Free
Half-hour before sunrise to half-hour after sunset
Dogs: No · Bikes: Designated trails (popular with mountain bikers)

2,820 acres of dense redwood and Douglas fir forest along Skyline Ridge. Trails wind through second-growth redwoods, past enormous old-growth stumps from 1800s logging, fern-covered hillsides, and unique tafoni sandstone formations — honeycomb-weathered outcrops that are a geological highlight. The Methuselah Trail passes the preserve's most impressive ancient trees. Banana slugs galore in wet conditions. Ocean views possible on clear days from western trails.

10. Russian Ridge Open Space Preserve

2–8+ mi loops · 200–800 ft gain · 30–35 min from property
Parking: Vista Point lot at Alpine Rd. & Skyline Blvd. · Free
Half-hour before sunrise to half-hour after sunset
Dogs: Yes, on leash (designated trails) · Bikes: Designated trails

High-elevation grasslands and wildflower meadows along Skyline Ridge. One of the most open, expansive preserves on the Peninsula. On clear days, views extend from the Pacific Ocean to the Bay and beyond to Mt. Diablo. Spring wildflowers (April–May) blanket the hillsides in lupine, poppy, and paintbrush — one of the best wildflower hikes in the Bay Area. Exposed ridgeline means it's windy and cold even when the valley is warm. Connects to Coal Creek and Skyline Ridge preserves for longer adventures.

Trail resources: Midpeninsula Regional Open Space District for official maps and closures. Bay Area Hiker for detailed trail descriptions. AllTrails for GPS maps and conditions reports.

For nearby dining after your hike, see our Dining & Drinks guide. For more outdoor activities in the area, see Day Trips from Palo Alto & Menlo Park.