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 Alameda Creek Regional Trail. With more than 83 trails covering 664 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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The Matadero Creek Trail, also known as the Page Mill-Arastradero Connector, offers beautiful views of the San Francisco Bay and Santa Cruz Mountains as it winds its way through gently rolling hills...
The Visitacion Valley Greenway is a recreational gem tucked into a residential neighborhood in southern San Francisco. The paved pathway connects a series of small parks that offer a plethora of fun...
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 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.
The Lafayette-Moraga Regional Trail links its two namesake communities via a former logging railroad corridor that largely parallels St. Mary's Road. Uniquely, mules hauled lumber on the corridor...
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...
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 NWP Railroad Trail runs on an arrow-straight course through Larkspur and Corte Madera in ritzy Marin County. Its name is derived from the railroad that once made use of the corridor: the...
The Centennial Way Trail follows the path of the BART line between San Bruno station and South San Francisco station. The BART, of course, runs underground while the trail doesn't. The 10-foot-wide...
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...
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...
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 Ohlone Loop Trail offers a birder's paradise in a wetland area of Watsonville on California's central coast. Its location, bordering a residential area, provides easy access for residents to...
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...
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This segment of the California Coastal Trail (also known as the Half Moon Bay State Park's Coastside Trail) runs parallel to the Pacific Coast along what used to be the Ocean Shore Railroad. The...
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...
Winding along the Pacific coast, the Monterey Bay Coastal Recreation Trail offers breathtaking views of the Pacific Ocean and a great way to tour Monterey and adjacent communities while enjoying the...
The Lower Silver Creek Trail runs in a nearly straight line between Ocala Avenue and Dobern Avenue (Abed Court). Between Foxdale Drive and Logsden Way there's a short (about 0.25 mile) on-street...
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...
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 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...
The Stevens Creek Trail is open in two disconnected segments in Mountain View and Cupertino, two of Silicon Valley's growing communities. As its name suggests, both segments closely follow Stevens...
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...
This extremely scenic rail-trail is located in the majestic Forest of Nisene Marks State Park near Aptos, California. The park was the site of major logging operations by the Loma Prieta Lumber...
The Crystal Springs Regional Trail is a developing network made up of three distinct portions: the San Andreas segment, Sawyer Camp segment and Crystal Springs segment. The two northern segments are...
The Matadero Creek Trail, also known as the Page Mill-Arastradero Connector, offers beautiful views of the San Francisco Bay and Santa Cruz Mountains as it winds its way through gently rolling hills...
The Upper Struve Slough Trail is part of a network of trails running through Watsonville's wetlands, offering a natural, outdoor experience and birding hotspot right in the heart of an urban area. The...
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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...
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...
The Great Highway Bike Path parallels its namesake road on the western edge of San Francisco, offering stunning views of the Pacific Ocean throughout. The trail provides direct access to the San...
The Beach Range Road Multi-Use Trail runs parallel to State Route 1 along the Pacific Coast, offering a safe alternative for commuters in Sand City, Seaside and Marina, and for students attending...
The Mori Ridge Trail is one trail of many in beautiful Sweeney Ridge, a prime bicycling and hiking area in San Mateo County. The natural surface path runs from a junction with both the Sweeney Ridge...
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 Umbarger Road Parkway parallels its namesake road for just over 0.5 mile between Plumas Drive and Tuers Road in a narrow strip of greenspace surrounded by suburbia. The similar Barberry Walkway is...
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.
The Black Diamond Railroad Trail is within the Black Diamond Mines Regional Preserve, a splendid place to visit with a fascinating and unique history. From the 1850s to the early 1900s, the region was...
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 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 Delta de Anza Regional Trail is 15 miles long, running between Willow Pass Road at Route 4 near Concord and Main Street (Rt. 4) at E. Cypress Road in Oakley. The eastern end in Oakley intersects...
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...
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 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 Mori Ridge Trail is one trail of many in beautiful Sweeney Ridge, a prime bicycling and hiking area in San Mateo County. The natural surface path runs from a junction with both the Sweeney Ridge...
The Guadalupe River Trail is the spine of San Jose's growing trail network, running north-south through much of the city. Portions of the trail run along both banks of the Guadalupe River, with signs...
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,...
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...
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 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 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...
The San Lorenzo River Parkway Trestle Trail is the first completed segment of the Coastal Rail Trail, which will eventually run 32 miles from Davenport to Watsonville. The segment from Santa Cruz to...
The Penitencia Creek Trail follows its namesake creek through a suburban greenbelt in northeast San José. On the northeastern end, the trail passes by a series of percolation ponds, and you can take a...
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...
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...
The West Cliff Drive Bicycle Path is just over 3 miles long, but, with its gorgeous backdrop of ocean waves and dramatic cliffs, you'll wish it was longer. The fairly flat, paved trail winds its way...
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 Embarcadero Bike Path is an important connector between the local commuter rail, schools, and a commercial area on Palo Alto's west side and the outskirts of Stanford University. The paved...
A half mile of the East Bay Greenway is currently open from the Coliseum BART Station (at 75th Avenue) to 85th Avenue in Oakland. The paved trail parallels San Leandro Street with traffic signals and...
The Watsonville Slough Trail follows its namesake waterway through a residential area of the city. It's part of a system of trails in a wetland area abundant with birds; you might see ducks,...
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...
The Matadero Creek Trail, also known as the Page Mill-Arastradero Connector, offers beautiful views of the San Francisco Bay and Santa Cruz Mountains as it winds its way through gently rolling hills...
I literally grew up on this trail, back when it was unpaved, and was just some weird, seldom-used backwater ie., prior to the early 1980s or thereabouts, at which point it started getting much more developed & popular. I have seen (quite large!) blue herons on (or adjacent) to this trail many times, and in 1995, I once saw a bobcat (at night, between Vasona dam and Lark Avenue). There are many turtles, and about 40 years ago, I once saw a Northern Pike (just behind Vasona dam). I've witnessed scores of salmon spawning at the Camden Avenue dam.
Gorgeous day in Half Moon Bay - what a terrific opportunity to explore this trail! It appears that many enjoy its wonders as well...pretty remarkable, considering this is the middle of the week! There were walkers, bikers, and dogs on the path - everyone was very respectful of passing each other and sharing the width of the path.
Nice to have the ocean 'on your shoulder' as you move up and down the path, as well as seeing all the wildlife - hawks, herons, rabbits to name a few!
I rode part of this trail last week, from Pacific Grove up to the town of Seaside. It is quite scenic, in spots, but you also ride through some urban congestion and cross a number of busy intersections. It's also not very well marked. I got some advice from Adventures By the Sea, an outfitter located at the beginning of the trail, that was very helpful given the relative lack of signage. Maybe this trail gets quieter and more protected from traffic as you get further from Monterey, but I decided to turn around and ride part of the 17 Mile Drive instead when I hit the busy intersection at Seaside. If I try it again, I think I'd rather start in Castroville, at the northern end, and ride south.
It is awesome my sister and I play there all the time!! Great surrounded park area!!
Whenever we visit the Monterey Peninsula, we always make sure to ride our bikes or walk multiple times on the Monterey Bay Coastal Recreation Trail. Very few places in the world can match the beauty and splendor of this trail, especially between Lovers Point Park in Pacific Grove to the Wharf in Monterey. This portion of the trail is most certainly perfect for visitors and walking enthusiasts.
Beyond the wharf up to Castroville (the Artichoke Capital of the World) is for individuals looking for a much more intense workout.
If I lived on the peninsula, I'd be somewhere on that trail every day!
On a gray May morning in 2018, my wife and I headed north from Pacific Grove to ride the West Cliff Path. We parked on Swanton Blvd., which is pretty much right at the trailhead, and then headed down the smooth asphalt path/promenade.
The path has spectacular ocean views, plenty of benches to relax upon, restored Victorian homes, art installations, a surf museum, huge amounts of surfers, an extra long pier with a residence of sea lions, a multitude of photo ops, and even an amusement park when you reach the end.
At the trail's end consider continuing across the San Lorenzo River and navigating some quiet residential streets to get a better view of the Walton Lighthouse and look back up the coastline.
Even though we rode on a weekday morning, the path had quite a bit of use by walkers, joggers, dog walkers, amusement park goers, and surfers. It slows you down a bit, but that's OK since to ride this trail is all about the essence of the scenery!
With the exception of one hill as you descend the cliff down to sea level near the pier, it's all flat which is perfect for a couple of sixty somethings.
All in all, it's a path to be taken slowly and to be savored, an ideal experience!
Started at the Rosie the Riveter/World War II Home Front National Historical Park in Richmond and traveled south (clockwise) along the bay to the Central Ave intersection and return. A good portion of the trail is wide and plenty of room for walkers and bikers. The last couple miles we rode is a bit narrower, still enough room for both. Trail condition is great. A number of interpretative signs are placed, discussing the history and nature of this area. Well worth the visit. Take time to see the Rosie Visitor Center. Luck was with us when we visited and were able to attend a talk by the National Park Service’s oldest park ranger (97 yrs old). Betty Reid Soskin is an articulate speaker and recounted her time living in the area and working in the ship yards during WWII. If given the opportunity don’t miss out. Noted that the trail in this area had great signage and shouldn’t have any trouble following the route. Some of the trail going north (counterclockwise) was on the street with designated bike lanes. Looking forward to doing other sections of this trail when we visit again in the future.
Only rode a short distance of this trail from Trader Joe’s parking lot down to the West Cliff Drive Bicycle Path. Some traffic on this trail but not as much as the West Cliff path. Path condition was fine, not a real wide path but ok. A number of homeless folks hanging out on and along the path. Was panhandled while in Trader Joe’s parking lot. At no time did we feel uncomfortable with environment, just unfortunate.
Started the ride at Trader Joe’s parking lot along the Santa Cruz Riverwalk, rode downstream to the intersection with the West Cliff Drive trail. Then rode up the coast to the end of this trail. Trail in good condition and nice surface but lots & lots of other folks on the trail, mostly walkers. Great scenery of Santa Cruz bay, coastline, and surfers along the trail. So much traffic on the trail made it challenging. Once at end of trail decided it would be easier to ride the road. So on return trip stayed on the parallel road and sailed along without obstruction. Consider this as the return option.
We rode this in two sections.
First section started at Casa Verde Way and rode North to the intersection of Lapis Road and Hwy 1. Missed the first left turn to go over dunes (no directional signage) and after a short distance realized we needed to back track. Then at Lapis Road & Hwy 1 the trail appeared to end at this intersection (no directional signage), could have explored down the highway at little to find remainder of trail but by then had ridden about 15 miles, so called it at that point. We did divert off of this trail to ride the parallel Beach Range Road trail in Fort Ord Dunes State Park. That road is much wider and nicer to ride. Depending how long of ride you want but recommend ending at the North end of Beach Range Road and then return.
Second Section: Started again at Casa Verde Way heading south to end of trail at Lovers Point and return. This portion of trail has many more walkers and bikers but trail is wide enough for all and in very good condition. This portion has some great scenery, a number of interpretive signs along the way, stopped to watch the Harbor Seals at a number of stops. Highly recommend this portion of trail.
Connected on to this trail from the Monterey Bay Coastal Trail at the south end and rode to north end of trail. Nice wide paved trail/road that used to be a main road for Fort Ord (no longer used for vehicle traffic). At south end of trail a number of homeless camps and trash tossed around. Nothing threatening just an eye sore. A spur trail leads down to some old military munitions storage bunkers. A few information panels are along the trail. I went through basic training at Fort Ord and the trail passed by one of the rifle ranges we used, brought back some memories. Much better, wider, trail than the parallel running Monterey Bay trail.
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