01
Best overall pick
Sugarloaf Ridge State Park
Foothills East Of Kenwood • Waterfall And Summit State Park • Most Versatile Trail Network
Waterfalls, big views, and shaded creek canyons make Sugarloaf the go-to hiking hub right above Kenwood.
From the Canyon Trail to Bald Mountain’s fire-road grind, Sugarloaf packs a surprising variety of terrain into a compact footprint. You can keep it mellow with a family walk along Sonoma Creek or push for a thigh-burning climb that rewards you with one of the best 360-degree views in the valley. Parking fills on spring weekends, so locals either start early or aim for late-afternoon golden light.
02
Rugged ridge adventure
Hood Mountain Regional Park & Open Space Preserve
Ridge Between Kenwood And Santa Rosa • Rugged Backcountry Regional Park • Best Challenging Climb
Steep, rocky trails and a dramatic overlook above the valley make Hood Mountain the spot for hikers who want a real workout.
The main routes to the summit are sustained and often rocky, with sections that feel more like backcountry than wine country. On a clear day, the Gunsight Rock overlook gives you a bird’s-eye view down Sonoma Valley and, on the best days, all the way toward San Pablo Bay. Pack water, expect limited shade on the upper slopes, and treat this as a half-day outing rather than a casual stroll.
03
Classic oak woodland loop
Trione-Annadel State Park
Santa Rosa Side Near Spring Lake • Lakeside Oak Woodland State Park • Best Mellow Mileage
Rolling singletrack, wildflowers in season, and quiet loops around Lake Ilsanjo make Annadel ideal for longer but moderate hikes.
Annadel’s network of fire roads and singletrack lets you link together custom loops, from short leg stretchers to 10-mile rambles. Many hikers aim for Lake Ilsanjo as a turnaround point, using shady forest sections and open meadows for variety along the way. Expect some shared use with mountain bikes, but the scale of the park means you can usually find a quieter corner if you venture a bit farther from the main trailheads.
04
History-meets-nature escape
Jack London State Historic Park
Glen Ellen Countryside • History-Rich Hillside Park • Best History-And-Hike Combo
At Jack London, you can walk past ranch ruins and red barns before climbing into shady forests and open hilltop meadows.
Many visitors start by exploring the historic buildings, then follow the Mountain Trail or Sonoma Ridge routes for a proper hike. The trails transition quickly from vineyard edges and orchards into quiet oak and bay forest, with occasional breaks where you can look back over the valley. It’s an especially nice choice for mixed groups where some are more interested in stories and scenery than hard elevation gain.
05
Skyline ridge walk
North Sonoma Mountain Regional Park & Open Space Preserve
Bennett Valley Ridgeline • High Ridge Connector Trail • Best Skyline Traverse
The North Sonoma Mountain Ridge Trail offers a steady climb to long, airy views and a high-country feel surprisingly close to Kenwood.
From the lower trailhead, the path climbs through shady forest and pasture edges before breaking out onto an open ridge with sweeping views toward Sonoma Valley and the Mayacamas. On cooler days and clear evenings, locals come here for the sense of space and big sky rather than a technical challenge. If you have a car shuttle and strong legs, you can link this ridge toward Hood Mountain for a memorable point-to-point day.