A curated guide to Peninsula and South Bay hikes, brought to you by POST. LEARN MORE
POST protects open space on the Peninsula and in the South Bay for the benefit of all.
2025 Hiking Calendar
Brought to you by POST
POST protects open space on the Peninsula and in the South Bay for the benefit of all.
Get ready to explore the great outdoors year-round with our hiking calendar! Discover the best landscapes to visit each month and learn interesting facts about local plants and animals. Use this guide to inspire your next self-guided hike with family or friends.Looking for an organized group hike? Check out our events calendar.
Since 1977, POST has been hard at work protecting open spaces on the Peninsula and in the South Bay for the benefit of all. So far, we’ve safeguarded more than 89,000 acres of land — places for wildlife to thrive and for us to reconnect with nature.
The trails await!
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January
Jean Lauer Trail
Pillar Point Bluff
- Location
- [hike.location]
- Length
- 1.4-miles roundtrip
- Elevation Change
- 100 feet
- Hiking Time
- Less than 1 hour
- Difficulty
- [hike.trail_type]
This popular, dog-friendly and ADA-accessible trail offers spectacular ocean views. After crossing a seasonal wetland area, you’ll head to the coast where you may see pelicans, cormorants, or hawks flying overhead.
All Month:
- Steelhead return to spawning grounds
- Blood currants bloom
- Gray foxes mate
February
Castle Rock Falls
Castle Rock State Park
- Location
- [hike.location]
- Length
- 3.4 miles round-trip
- Elevation Change
- 1100 feet
- Hiking Time
- 2 hours
- Difficulty
- [hike.trail_type]
Winter is the perfect time to visit Castle Rock State Park, especially if it’s been raining. Hikers can stand on a wooden platform above a waterfall that careens 75 feet down into the San Lorenzo River. Besides chasing waterfalls, you’ll find impressive sandstone formations, sweeping vistas, and ancient redwoods.
All Month:
- Bobcats mate
- Snowy egrets nest
- Cottonwood bloom
March
Maisie’s Peak
Fremont Older Open Space Preserve
- Location
- [hike.location]
- Length
- 2.6 miles round-trip
- Elevation Change
- 500 feet
- Hiking Time
- 3 hours
- Difficulty
- [hike.trail_type]
Take a winding trek through beautiful forests and rolling hills to the top of Maisie’s Peak. At the summit, you’ll have panoramic views of the surrounding landscape. Keep an eye out for blue elderberry, coyote brush, and monkey flower along the way.
All Month:
- Western fence lizard emerge
- migrating birds arrive
- Coyote pup season begins
APRIL
Rancho Cañada del Oro
Rancho Cañada del Oro Open Space Preserve
- Location
- [hike.location]
- Length
- 5.8 miles
- Elevation Change
- 1460 feet
- Hiking Time
- 4-5 hours
- Difficulty
- [hike.trail_type]
You’ll find vibrant wildflowers at this preserve in the springtime, after the landscape has been renewed from recent rains. The trails here wind through native grasslands, oak woodlands, and creekside habitats. Bring a picnic and reward yourself after a challenging hike!
All Month:
- wildflowers bloom
- Western snowy plovers nest
- Bay checkerspot butterfly mate
MAY
Long Ridge Trail
Long Ridge Open Space Preserve
- Location
- [hike.location]
- Length
- 4.7 miles round-trip
- Elevation Change
- 500 feet
- Hiking Time
- 3 hours
- Difficulty
- [hike.trail_type]
This is a great hiking destination at all times of year, though spring is especially stunning with wildflowers putting on a show. At the top of the ridgeline, you’ll discover sweeping views of the Pacific ocean and Santa Cruz Mountains.
All Month:
- Harbor seal pupping season
- Rattlesnakes mate
- Artichokes in season
June
Cowell-Purisima Trail
Cowell Ranch State Beach
- Location
- [hike.location]
- Length
- 3.6 miles
- Elevation Change
- 100 feet
- Hiking Time
- 2 hours
- Difficulty
- [hike.trail_type]
Take in two highlights of the San Mateo County coast along one trail! You’ll have farmland on one side and ocean views on the other. It’s a wonderful outing for everyone in the family — perfect for a slow, meandering hike. Keep an eye out for harbor seals, pelicans, hawks, and wildflowers.
All Month:
- Strawberries ripen
- humpback whales arrive
- Juvenile Badgers leave their dens
July
High Meadow Trail Loop
Rancho San Antonio Open Space Preserve
- Location
- [hike.location]
- Length
- 5.5 miles round-trip
- Elevation Change
- 800 feet
- Hiking Time
- 4-5 hours
- Difficulty
- [hike.trail_type]
The trail begins in a cool canyon and then ascends to high meadows featuring sprawling views. Pause at the quaint Deer Hollow Farm near the start of the trail to see gardens and animals.
AUGUST
Skyline Trail
Sanborn County Park
- Location
- [hike.location]
- Length
- 6 miles round-trip
- Elevation Change
- 600 feet
- Hiking Time
- 5-6 hours
- Difficulty
- [hike.trail_type]
Escape the heat on this mostly flat, completely shaded trail. You’ll journey along the ridgeline of the Santa Cruz Mountains through dense forests of Douglas fir and Pacific madrone.
All Month:
- Blackberries ripen
- Pallid Bat Pups Take Flight
- Rattlesnakes Born
- Coyotes Born
SEPTEMBER
Devil’s Slide Trail
San Mateo County Park
- Location
- [hike.location]
- Length
- 3 miles round-trip
- Elevation Change
- Mostly flat
- Hiking Time
- 2 hours
- Difficulty
- [hike.trail_type]
Converted from a former section of Highway 1, this short, paved trail is a destination for both walkers and nesting seabirds. Plus, the ocean views cannot be beat! This time of year, bring binoculars to spot humpback whales swimming further offshore.
All Month:
- California Aster bloom
- Big Leaf Maples Change Color,
- tarantulas mate
OCTOBER
Levee Trail
Stevens Creek Nature Study Area
- Location
- [hike.location]
- Length
- 1 mile round-trip
- Elevation Change
- Mostly flat
- Hiking Time
- 30 minutes
- Difficulty
- [hike.trail_type]
If you’re a birder, you’re in luck. Though this trail is short and sweet, it’s an ideal place to observe swallows, sandpipers, herons, coots, shovelers, and more. Plus, you can easily extend the hike along the San Francisco Bay Trail.
NOVEMBER
Spring Ridge to Summit
Windy Hill Open Space Preserve
- Location
- [hike.location]
- Length
- 7.5 miles round-trip
- Elevation Change
- 1400 feet
- Hiking Time
- 2-3 hours
- Difficulty
- [hike.trail_type]
On a clear day, three mountain peaks are visible from the summit: Mt. Diablo, Mt. Hamilton, and Mt. Tamalpais. Though a strenuous hike to the very top, the stunning views make the journey worthwhile.
All Month:
- Migrating Birds Arrive
- Coastal Monarch Populations peak
DECEMBER
Sam McDonald’s Cabin
Sam McDonald County Park
- Location
- [hike.location]
- Length
- 2.8 miles round-trip
- Elevation Change
- 600 feet
- Hiking Time
- 2 hours
- Difficulty
- [hike.trail_type]
This moderate hike through the redwoods leads to the cabin where Sam McDonald, Stanford’s first Black administrator, once lived. Keep an eye out for banana slugs and California newts, who are more common during the wet winter months.
All Month:
- northern elephant seals breed
- California tiger salamanders migrate
- Anna's hummingbirds begin mating
POST protects open space on the Peninsula and in the South Bay for the benefit of all.
© 2024 Peninsula Open Space Trust
