01
Best overall pick
Zanja Peak Trail
Foothills Above Highland • Steep Local Summit Climb With Wide Valley Views • Local Favorite For Sunrise And Sunset
A short but punchy climb straight out of Highland into the chaparral, rewarded with sweeping views over the city and the San Bernardino Valley.
Zanja Peak is the go-to local hike when you want real elevation gain without a long drive into the high country. The route follows a mix of dirt road and singletrack up a prominent ridge, with open slopes that stay sunny and dry most of the year. Start early on hot days, bring plenty of water, and plan to linger at the top to spot landmarks from downtown Highland to distant peaks.
02
Most photogenic stop
Heart Rock Trail
Near Crestline Off Highway 138 • Shaded Creek Canyon Hike To A Waterfall • Best For A Quick Mountain Escape
A short forest walk along Seeley Creek that ends at a small waterfall and the famous heart-shaped pool carved into the rock.
From Highland, a scenic drive up Highway 330 and 18 drops you into cooler air and tall pines before you hop onto this mellow trail. The path meanders beside the creek, with just enough up-and-down to feel like a hike without intimidating newer walkers. Go early on summer weekends if you want quiet time at the rock and pool, as this spot draws day-trippers when the temperatures climb in the valley.
03
Best relaxed loop
Lake Gregory Trail
Lake Gregory Regional Park • Gentle Lakeside Loop With Forest And Water Views • Easy Scenic Loop
A mostly level path circling Lake Gregory, ideal for an unhurried walk with mountain air, shoreline scenery, and frequent benches.
The Lake Gregory loop is a great choice when you want fresh air without a hard climb, or when you are introducing friends to the local mountains. The trail hugs the water, with short boardwalk sections, side paths to small beaches, and views back to the surrounding ridges. It works equally well for a brisk training lap or a slow stroll with coffee and plenty of photo breaks.
04
Best for families
Dogwood Campground Loop
Near Running Springs Along Highway 18 • Quiet Pine Forest Loop With Interpretive Signs • Best For Families And New Hikers
A mellow loop through mature pines and dogwoods just off Highway 18, with soft trails, shade, and kid-friendly terrain.
This loop starts right from Dogwood Campground, making it an easy add-on if you are camping or a low-stress outing if you are just driving up for the day. The grade stays gentle, the footing is mostly smooth, and interpretive signs add a bit of natural history along the way. It is a smart pick for mixed-ability groups or anyone easing into mountain hiking from Highland.
05
Best big-day objective
San Bernardino Peak Trail
Angelus Oaks Along Highway 38 • Long High-Elevation Trek Into The San Gorgonio Wilderness • Big-Mountain Challenge
A demanding all-day climb from Angelus Oaks to a high summit ridge, with classic San Gorgonio views and a true backcountry feel.
If you are ready to graduate from foothill hikes, this is the closest taste of true high-country trekking to Highland. The trail winds up through oak and pine, past water sources early on, and eventually breaks onto open slopes with huge views toward the Inland Empire and deeper into the San Gorgonio range. Start pre-dawn, check seasonal conditions and permit requirements, and treat it as a full-value mountain day rather than a casual outing.