Explore the best rated trails in Cupertino, CA. Whether you're looking for an easy walking trail or a bike trail like the NWP Railroad Trail and Umbarger Road Parkway. With more than 90 trails covering 694 miles you’re bound to find a perfect trail for you. Click on any trail below to find trail descriptions, trail maps, photos, and reviews.
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Silver Creek Valley Trail follows its namesake creek and paralleling Silver Creek Valley Road. The passes through a country club neighborhood and through open space over a steep hill. The trail offers...
The Santa Cruz Riverwalk Trail follows both sides of the river through downtown Santa Cruz, a California beach town on the shores of Monterey Bay. Multiple pedestrian bridges allow easy access to the...
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This 2.5-mile trail segment through San Francisco's Presidio is part of 340-mile network of multi-use trails collectively known as the Bay Area Ridge Trail that climb Bay Area mountain ridges and pass...
The Albertson Parkway is located in South San Jose, just steps away from the sprawling Santa Teresa County Park, which features preserved land and unpaved trails in the rolling Santa Teresa Hills. The...
The Bol Park Path is a charmer that threads through a peaceful Palo Alto neighborhood in the hills south of San Francisco. At its heart is Bol Park, a strip of playground and lawn laid alongside...
The Highway 87 Bikeway follows State Route 87 between Willow Street in the north and Santa Teresa Boulevard at W. Valley Freeway (SR 85) in the south. Basically, the trail forms the missing link...
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Tucked in the quiet Oakland hills neighborhood of Montclair, the Shepherd Canyon Trail (a.k.a. Montclair Railroad Trail) is a popular community rail-trail that has come to symbolize the power of...
About 35 miles south of San Francisco, the Cowell-Purisima Trail offers a beautiful escape into nature which can be enjoyed by both walkers and bicyclists. Travelers in wheelchairs can also access the...
The Mill Valley/Sausalito Multiuse Pathway is a convenient connection between neighborhoods, schools, shopping, restaurants, and both a skate and dog park. The short dirt section at the north end is...
The Highway 237 Bikeway parallels State Route 237 between McCarthy Boulevard in Milpitas and Calabazas Creek in Sunnyvale. The trail consists of two main segments: the first is between McCarthy...
The Isabel Avenue Trail runs north-south on the western boundary of Livermore in the eastern San Francisco Bay area's Tri-Valley region. As its name suggests, the path primarily serves neighborhoods...
If you're looking for a gentle rail-trail in Marin County that offers stunning views of both San Francisco Bay and Mt. Tamalpais, the Tiburon Historical Trail is for you. Known alternately as the...
The Baine Avenue Trail is a short rail-with-trail along an active Union Pacific Railroad corridor in the heart of Newark. The unpaved trail is most useful as a neighborhood connector or short...
Nimitz Way links Tilden Regional Park and Wildcat Canyon Regional Park via the ridge between Wildcat Creek and the San Pablo Reservoir on the northern outskirts of Berkeley. The paved 4-mile trail...
The Sabercat Creek Trail can be found along its tree-lined namesake waterway in the Mission San Jose community of Fremont, a coastal California city off the San Francisco Bay. The 2-mile paved pathway...
It is difficult to travel through suburban Santa Clara County for more than a few minutes without noticing an abundance of cyclists and runners in the area. If you are strolling to downtown Los Gatos,...
The Permanente Creek Trail offers a linear route through the suburban city of Mountain View, beginning at Shoreline At Mountain View and heading south to Rock Street. The paved pathway includes safe...
The Calero Creek Trail runs between Singer Park and Santa Teresa County Park. The trail is paved between Los Alamitos Creek and Harry Road (0.7 mile) and has a gravel surface between Harry Road and...
Named for the Ohlone Indians who once lived in the area, this trail doubles as a commuting corridor and a recreation destination for the cities of Berkeley, Albany and El Cerrito. While the Ohlone...
The bulk of the High Canal Bridge Pathway runs alongside its namesake waterway, offering scenic views and a sense of serenity in the middle of the ritzy Marin County communities of Larkspur and Corte...
The Cross Alameda Trail is a four-mile developing trail that will someday stretch from one end of Alameda island to the other, from the Seaplane Lagoon Ferry Terminal in the west to Fruitvale Bridge...
This innovative road-to-trail project opened for public use in March 2014. The trail, which features stunning Pacific Ocean views, makes use of a former portion of California's State Route 1, which...
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The Three Creeks Trail will one day span 3 miles through San Jose's Willow Glen neighborhood. In 2018, the western leg of the trail opened, stretching nearly a mile from Coe Avenue to just south of...
Naomi Patridge Trail is a 2 mile coastal trail paralleling Highway 1 in Half Moon Bay, California. The trail was named for a longtime San Mateo Councilwoman, prominent volunteer and lifelong Half Moon...
The Montgomery Hill Trail is a short dirt trail traversing Montgomery Hill Park, an undeveloped green space in San Jose. The trail offers nice views of the surrounding area and links Yerba Buena Creek...
The Southern Pacific Railroad Right-of-Way passes through residential neighborhoods on the west side of Pacific Grove, providing a nice walking and biking spot for residents and visiting tourists to...
The Sweeney Ridge Trail is one trail of many in beautiful Sweeney Ridge, a prime bicycling and hiking area in San Mateo County. Inaccessible by automobile, the trail must be reached by any of its...
The Baquiano Trail is one trail of many in beautiful Sweeney Ridge, a prime bicycling and hiking area in San Mateo County. The trail climbs 550 feet from a junction with two hiking trails in the west...
The Sandra Marker Trail runs for a mile on an east-west course through Larkspur, linking the Redwood Highway/San Clemente Drive Paths in the east with the popular NWP Railroad Trail in the west. Both...
The Sneath Lane Trail is one trail of many in beautiful Sweeney Ridge, a prime bicycling and hiking area in San Mateo County. From a trailhead in the Crestmoor neighborhood of San Bruno, the paved...
The San Tomas Aquino Creek Trail offers a paved route running approximately 5 miles through Santa Clara along its namesake waterway. In the north, the trail connects to the Highway 237 Bikeway (a...
The bulk of the High Canal Bridge Pathway runs alongside its namesake waterway, offering scenic views and a sense of serenity in the middle of the ritzy Marin County communities of Larkspur and Corte...
The Evergreen Creek Trail follows its namesake creek between San Felipe Road and Yerba Buena Road. To the north of the gravel trail is suburbia (with a row of trees separating the trail from the...
Silver Creek Valley Trail follows its namesake creek and paralleling Silver Creek Valley Road. The passes through a country club neighborhood and through open space over a steep hill. The trail offers...
Nestled between Alum Rock Canyon and the Mt. Diablo foothills, Alum Rock Park west of San Jose is California's oldest city park. From the early to mid-1900s it was a popular resort and spa, complete...
Nimitz Way links Tilden Regional Park and Wildcat Canyon Regional Park via the ridge between Wildcat Creek and the San Pablo Reservoir on the northern outskirts of Berkeley. The paved 4-mile trail...
Tucked in the quiet Oakland hills neighborhood of Montclair, the Shepherd Canyon Trail (a.k.a. Montclair Railroad Trail) is a popular community rail-trail that has come to symbolize the power of...
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This 4.5-mile paved trail encircles Lake Merced in southwestern San Francisco. The western leg of the loop is also referred to as the Lake Merced Measured Mile and is part of a larger, regional effort...
Joe's Trail at Saratoga de Anza parallels the south side of the active Union Pacific Railroad tracks that travel through a residential area of Saratoga, a California community just south of the San...
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The Alamo Creek Bike Path snakes alongside its namesake stream through residential Dublin, Alameda County. The paved trail has spurs reaching into the nearby subdivisions, drawing residents onto the...
The Arroyo Mocho Trail is a part of a network of multi-use trails in Livermore and which also links with the city of Pleasanton. The trail provides access to neighborhoods, schools, numerous parks,...
The Evergreen Creek Trail follows its namesake creek between San Felipe Road and Yerba Buena Road. To the north of the gravel trail is suburbia (with a row of trees separating the trail from the...
The Albertson Parkway is located in South San Jose, just steps away from the sprawling Santa Teresa County Park, which features preserved land and unpaved trails in the rolling Santa Teresa Hills. The...
The Contra Costa Canal Trail forms a horseshoe shape route, traversing through the urban and neighborhood landscape of Martinez, Pleasant Hill, Walnut Creek and Concord. The trail follows the canal of...
Oakland's Lake Merritt Trail closely follows the lake's shoreline for a pleasant, paved trip with beautiful views and connections to several parks and attractions right in the heart of the city. The...
The Santa Cruz Coastal Rail Trail is a paved multi-use trail and it will eventually run 32 miles along California's Santa Cruz County coastline, from Davenport to Watsonville. Coastal Rail Trail...
The Aquatic Park Trail travels along a hairpin-shaped route through Aquatic Park and around a small lake narrowly separated from the San Francisco Bay. The trail runs parallel to, and across...
The Baine Avenue Trail is a short rail-with-trail along an active Union Pacific Railroad corridor in the heart of Newark. The unpaved trail is most useful as a neighborhood connector or short...
The Highway 87 Bikeway follows State Route 87 between Willow Street in the north and Santa Teresa Boulevard at W. Valley Freeway (SR 85) in the south. Basically, the trail forms the missing link...
If you're looking for a gentle rail-trail in Marin County that offers stunning views of both San Francisco Bay and Mt. Tamalpais, the Tiburon Historical Trail is for you. Known alternately as the...
The Highway 237 Bikeway parallels State Route 237 between McCarthy Boulevard in Milpitas and Calabazas Creek in Sunnyvale. The trail consists of two main segments: the first is between McCarthy...
The Barberry Walkway runs parallel to Barberry Lane between Corda Drive near Meadowfair Park and Dina Lane. There are plans to extend the walkway along the outskirts of the park to Quimby Road.
Silver Creek Valley Trail follows its namesake creek and paralleling Silver Creek Valley Road. The passes through a country club neighborhood and through open space over a steep hill. The trail offers...
Riding high on the cliffs at North America's western edge, this San Francisco-area trail offers unbeatable views of Golden Gate Bridge and the Pacific Ocean at San Francisco Bay. Add to that a chance...
Beginning in 1904, the Atchison, Topeka and Santa Fe Railway (AT&SF) carried freight through the city of Richmond, reaching its height during World War II when Richmond became a national leader of...
The Great Meadow Bike Path provides an important 1.5-mile transportation route from the main entrance of the University of California at Santa Cruz to the busy campus core. The trail is surrounded by...
The Quarry Lakes Regional Recreation Area provides users with a wide variety of recreational activities. In addition to its several miles of biking, walking and equestrian paths, the park also...
The Half Moon Bay State Park's Coastside Trail is a segment of the California Coastal Trail and runs parallel to the Pacific Coast along what used to be the Ocean Shore Railroad. The railroad itself...
Saratoga Creek Trail follows the winding course of the creek between just south of I-280 (Junipero Serra Freeway) and Saratoga Creek Park. The trail parallels the Lawrence Expressway/County Route G2...
The Los Alamitos Creek Trail runs along its namesake creek between McKean Road and Almaden Lake Park, where the trail is also known as the Lake Almaden Trail. From its southern endpoint to Camden...
If you're a fan of dedicated bike paths, and in the area, don't miss the opportunity to ride Lafayette-Moraga. Almost the entirety of the path is along a shaded corridor, gently curving back and forth, beautiful homes visible in wooded settings, quirky sections (e.g. a brief segment with many dozens of miniature bird houses hanging from trees), St. Mary's of Moraga's beautiful campus visible at one point.
I'd recommend starting from the Lafayette side. This trail is not flat: the out and back registered 600 vertical feet on Ride with GPS. Starting on the Lafayette side will result in about 5 miles of mildly climbing trail, a descent of about 2 miles at the far end, and then a somewhat steeper (but not steep) climb back to the summit. The last 4.75 miles of a round trip to Lafayette involves a swooping and delightful descent back to where you started. While the climbing is not negligible, it is well within the capabilities of even moderately fit riders.
My partner and I rode this trail on our tandem trike on a Wednesday, finding light to moderate foot and bike traffic. If you're family oriented, use caution with the younger riders, as on the downhill slopes some riders will be coming down in excess of the 15 mph speed limit.
Overall, a gem of a ride, scenic, interesting, and just enough of a challenge to feel that your heart and lungs benefited from a great day outside.
Took the Ferry to Larkspur and biked over the Bridge today to Point Richmond. Well maintained bike path, incline a bit challenging, so walked the bike for about one mile, I’m a novice and 67. Windy but views are worth it!
We didn't like the thought of leaving our car at the Castroville end loaded with stuff for a weekend trip, so we drove a short ways to Marina State Beach and started there. It's a short ride on not-too-busy streets to meet up with the trail just north of the Fort Ord section.
Loved the wide, uncrowded Fort Ord area and enjoyed the ocean views in the Sand City area, though some of that sand on the trail was pretty thick. The trail gets fairly crowded as you get into Monterey so we only took it as far as the wharf, about 10 miles from Marina Beach.
A beautiful ride, on our list of places to go again.
Cool sights in wildlife. People here are snotty techies¿. No one says hello back. But ride is nice out to the bay
If you start from Oakleys Big Break until the End in Brentwood it’s about a 20 mile RT. Safe, nice sites.
Good for walking & jogging but too busy for bicycles, skateboards, scooters. The street along side has a lot of traffic without a bike path so not very biker friendly. It's popular with pedestrians & dogs strolling along probably because there's an entrance to a dog friendly beach along the route. A lot of the route is along the top of a bluff with beach below so it gets very windy and can be cold if not sunny. Beaches are narrow & rocky and more for surfing. The path is nicely paved making it easy to walk.
This is a fantastic, scenic trail that is very protected for bikes. Can't wait to ride it again.
Being on this trail is a lovely escape from the city streetscape. In the works now is County action to close the cement plant at the end of the RR spur this trail adjoins. When that happens, there is a County adopted plan for the trail to extend all the way from Los Gatos to Rancho San Antonio Open Space!
This trail is a good length for a stroll. It is hilly and scenic. It is in a valley. The trail is asphalt with cracks sealed with tar. Except for the east end, which is concrete and very wide. I don’t recommend it for skating because it is rough and short. Also the hill at the west end near the bathrooms/parking is very steep.
I started on the north side, this is a nice walk with small children. After crossing the first road to the south there is a park on the right, pretty good for children.
In July, 2021, trail was extended south 1/3 mile to Linda Vista Park in Cupertino.
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