Kid-Friendly Hike to a Playground in Kensington - 510 Families
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Kid-Friendly Hike to a Playground in Kensington

Looking to switch up your family hiking routine? With sweeping views of Tilden Park and Wildcat Canyon, gentle slopes, and plenty of shade, Ye Olde School Trail in Kensington is an ideal hike for families. There’s even a playground just steps away from the out-and-back route!

Child hiking along wooded path with coat on
Views from Ye Olde School Trail can’t be beaten | Photo: Maureen Burke

What to Expect on this Kensington Hike

Ye Olde School Trail is a local gem. It’s an old fire road that doubles as a walking path for elementary school kids. Regardless of its origins, this trail is worth a drive into the hills. It’s become a recreation spot for families, dog walkers, and nature enthusiasts.

The path is an out-and-back loop that’s a total of about 1.5 miles long. You’ll spot plenty of birds, hills, trees, and plants on your hike. Take in the quiet and bucolic atmosphere. The trail isn’t overly challenging and does not overlook sheer drop-offs, but there may be a few stops that require hand-holding or careful footing. Overall, I would not recommend using a stroller (even an all-terrain one) because of the numerous bumpy tree roots and one extreme dip. For similar reasons, this trail isn’t wheelchair accessible.

On the weekends, our family likes to add a short walk to the local playground at Kensington Park. The path is also very close to the Kensington Library and Blake Gardens, for an extended adventure.

Mother and daughter on hiking trail
Take a leisurely hike as a family | Photo: Maureen Burke

Plan Your Hike on Ye Olde School Trail

To hike Ye Olde School Trail, start at the corner of Grizzly Peak Blvd and Kenyon Ave. There’s a small parking area and plenty of street parking. Follow the trail for about half a mile and you’ll come to the backside of Hilltop Elementary School. Turn around or continue along the south side of the building to walk down the stairs to Kensington Park.

Because it’s an out-and-back trail with lots of local offshoots (choose the middle path to reach the end), the path provides a level of flexibility. You can follow my family’s method or discover your own way to trek through the trail.

What to Do With Kids in Kensington >

Tips for hiking Ye Olde School Trail with kids

Ye Olde School Trail is a local favorite, especially among dog walkers. Your family will likely encounter several off-leash dogs along this path.

Hilltop Elementary School sits along the trail. Hikers are not allowed onto school property during school hours (8 am-3 pm). There are signs posted on the school’s fence to remind passersby. The schoolyard playground is tempting but opt for visiting Kensington Park’s playground, which is just steps downhill.

Child climbs on playground in Kensington, CA
Hike to the playground at Kensington Park | Photo: Maureen Burke

Kensington Park is a charming green space with several fields, sports courts, a playground, and swings. There are clean restrooms on the south side, near the tennis courts. Fill up your water bottles and take a quick snack break at the picnic tables to reenergize for the hike back to the trailhead.

Extend your time in Kensington with a stop at The Kensington Library just down the hill from the park. It’s open Tuesday through Saturday (see hours). There’s public parking here if you prefer to start the hike with playground time. Alternatively, stroll down Rincon Road to the beautiful Blake Gardens during non-holiday weekdays.

Child walks down stairs to park
Near the school, take the stairs down the hill to the park | Photo: Maureen Burke

The trail cuts through the edge of Tilden Park’s wilderness and you may see an occasional wild animal, such as a deer or bobcat. This is true for many trails in the East Bay and hasn’t deterred our family.

Tell us, have you hiked Ye Olde School Trail?

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