Outbound Collective logo

Cupertino, California

The best Trails and Outdoor Activities in Cupertino, California are a must-visit for those seeking outdoor adventures. The Fremont Older Open Space Preserve is a top choice, with over 14 miles of trails for hiking and horseback riding. The trails wind through scenic grasslands and oak forests, offering stunning views of the Santa Clara Valley. The Seven Springs Loop Trail is another great option, featuring a beautiful creek and a variety of bird species. For a more challenging hike, the Black Mountain Trail at Monte Bello Open Space Preserve offers steep climbs and panoramic views of the Pacific Ocean. Don't miss the Stevens Creek Reservoir, a popular spot for fishing and boating. These are just a few examples of the best outdoor activities and attractions in and near Cupertino.

Top Spots in and near Cupertino

  • Santa Cruz, California

    Hike Natural Bridges to Lighthouse Field

    3.5
    4.8 mi / 121 ft gain
    This is a paved trail that can be used for hiking, jogging, or walking.  It offers over 2 miles of beautiful California coast.  Walk through flowers, see the jagged cliffs, and of course the lighthouse at the end!  This walk can be done from either direction.  Start at Natural Bridges and head We...
    Read more
  • Santa Cruz, California

    Surf Cowell's Cove

    4.8
    Cowell's Cove is located just south of Santa Cruz’s iconic Steamer Lane. The break is a slow pealing right, and is a very user-friendly wave for beginners. It can get crowded on weekends, especially when it's sunny, but no need to worry, there are a lot people out on foam boards and most are begi...
    Read more
  • Santa Cruz, California

    Surf the Hook

    4.0
    The hook is a surf spot found on the east side of Santa Cruz, located along East Cliff drive.  If you keep driving past Pleasure Point, you'll get to it.  It's a right hand point break that is usually smaller in size than Pleasure Point.  It's a very crowded spot due to the easy access parking lo...
    Read more
  • Livermore, California

    Paddle Lake Del Valle

    4.0
    Lake Del Valle is a reservoir located in Livermore, California. The lake has boat motor boats, pedal boats, patio boats, canoes, and row boats available for rent. There is a dock and rental  house in the marina.The lake is also a popular destination for picnics, barbecues, and camping. Parking fi...
    Read more
  • Livermore, California

    Hike the East Shore Trail Loop

    3.7 mi / 1040 ft gain
    This hike is best done during the spring, fall, or winter when moderate temperatures make the hike more comfortable. Be warned that this hike has a large elevation change despite being less than 4 miles. Starting at the Arroyo Road Staging Area, take the East Shore Trail east, heading towards a s...
    Read more
  • Santa Cruz, California

    Surf Pleasure Point

    4.0
    Pleasure Point is located on the east side of Santa Cruz, California. It is a right hand point break that breaks year round. It is a popular surf spot for many people that live in the San Francisco Bay Area.  There are 3 different peaks that break at Pleasure Point. Sewers, which is the furthest ...
    Read more
  • Santa Cruz, California

    Beach Day at Lighthouse Field State Beach

    4.0
    This beach is less crowded compared to other beaches in Santa Cruz.  I got there early on a Saturday and found easy street parking.  There was plenty of space to spread out on the soft sand.  Later in the day I saw dolphins several times!  This is close to the Santa Cruz Surfing Museum.  It’s als...
    Read more
  • Santa Cruz, California

    Natural Bridges State Beach

    4.3
    Natural Bridges State Beach is a wonderful place to photograph located in Santa Cruz off of West Cliff Drive. This is a great place to practice long exposure photography to capture awesome water movement as it passes through the "Natural Bridge" formation. The best time to shoot this spot is at ...
    Read more
  • Santa Cruz, California

    Surf at Natural Bridges State Beach

    4.5
    Natural Bridges is off of West Cliff Drive to the north of popular Santa Cruz break, Steamer Lane. The break is a right point break, which breaks on a rocky shelf and reef. The break is best during sizable swells (NW, SW, and West) and a low tide. Be sure to check the wind, this break gets blown ...
    Read more
  • Santa Cruz, California

    Photograph Monarch Butterflies at Natural Bridges' Monarch Grove

    4.3
    The park's Monarch Grove provides a temporary home for thousands of Monarchs. From late fall into winter they make this their home and if you time it perfectly you can see them in clusters in the trees.  When you reached the Natural Bridges State Park, on the right of the Visitors Center you'll f...
    Read more
  • Livermore, California

    Del Valle Regional Park

    4.0
    Looking for a quick summer escape filled with stand up paddling, canoeing, fishing, hiking, and picnics? Look no further than Del Valle Regional Park. Consistently considered one of the best campgrounds in the Bay Area, the centerpiece of Del Valle is a 5-mile long lake that allows swimming, fish...
    Read more
  • Burlingame, California

    Hike the Ed Taylor Loop Trail in Mills Canyon

    4.0
    1.4 mi / 300 ft gain
    This hike can be done at any time of year. Hiking in winter and spring means that many varieties of wildflowers will be present, and the creek will have much more water. Summer and fall mean higher temperatures and drier conditions, but the hike is still a pleasant experience. Begin the hike at t...
    Read more
  • Half Moon Bay, California

    Paddle Half Moon Bay Jetty

    The Half Moon Bay Jetty is a calm place to paddle as it is covered on all sides. There is an opening into the ocean on the far side, but is mostly calm with plenty of beach area to launch. Keep in mind, there are boats in the harbor so keep an eye out. There is also a scenic hike nearby the West ...
    Read more
  • Castro Valley, California

    Lake Chabot Regional Park Loop

    4.0
    8.65 mi / 1263 ft gain
    Looking for a fun day on a lake, but don't want to drive too far? We recommend heading out to the East Bay where you can combine a nice hike with an afternoon of fishing. This moderately challenging hike remains scenic throughout the 8.5 mile trek around the lake, and offers many opportunities fo...
    Read more
  • Morgan Hill, California

    Backpack to Coit Lake

    5.0
    26 mi
    This trail can be started from Coe Headquarters or Hunting Hollow Trailhead. The trail from Coe HQ is 2 miles longer, almost all elevation but provides beautiful views of the surrounding mountains. These directions will be starting from Coe HQ.Follow the loop around the parking area to the backpa...
    Read more
  • Morgan Hill, California

    Backpack to Mississippi Lake

    5.0
    26.4 mi / 3600 ft gain
    If you're tired of trying and failing to get reservations for backcountry camping around the bay area, then Henry Coe State Park is the perfect place to visit. No reservations need to be made prior to the trip. All you need to do is get to the HQ on the morning of your trip, get your permits and ...
    Read more