WOODSIDE WALKING TRAILS
A Guide to Walking in Woodside
Explore the beauty of Woodside on foot!
Our network of sidewalks, nature paths, and scenic trails offers something for everyone — from casual walkers to avid hikers.
The Woodside perimeter sidewalk
7.0 miles
This lollipop-shaped sidewalk trail is Woodside’s most popular walking route and is within easy reach of most homes. It also connects to several nature trails. The “stem” section is 1.0 mile, and the loop portion adds another 6 miles
The Village Trails
The Village at Woodside features multiple paved and lighted walking routes, linked to Woodside by a ¼-mile connector from the Reserve Club parking area. Inside the Village, enjoy several circular walking paths and a 1.5-mile Perimeter Nature Trail through scenic natural terrain.
The Reserve Park Oval
0.25 miles
Located beside the Reserve Club, this ¼-mile paved track offers a beautiful horticultural setting for walking or jogging. Parking is available adjacent to the track. Whether you’re out for an easy stroll or a power walk, this is a great spot to get moving.
The Meadows Loop Trail
0.6 miles
A flat, dirt path looping around the Meadows community — ideal for a short, easy walk. Add 0.2 miles by including the sidewalk around the Meadows Park. Parking is available near Meadows Park.
The Creek Walk
0.5 miles
This shaded, circular trail follows Cottonwood Creek, crossing it several times on wooden bridges. Enjoy an observation deck, a small nature library, and plaques highlighting native trees and plants. A cool, peaceful retreat on warm days. Parking: At the end of Cottonwood Creek Lane, or there is also a well-marked pedestrian access point from the Woodside perimeter sidewalk
The Mill Road Trail
1.0 mile in & out trail
A scenic ½-mile one-way trail along the northeast side of the Hollow Creek Land Preservation Area (HCLP). The trail currently ends near the 16th green of the Reserve Golf Course and returns along the same route. Access to the trail is from the Trail Head Parking area.
The Oakman Trail
2.1 miles
This lollipop-shaped nature trail combines wooded paths, golf cart lanes, and a section of the Perimeter Sidewalk. It winds between the 5th and 6th holes of the Reserve Golf Course, crosses the Oakman Lake Dam, and loops back through the woods. Access: From the Trailhead Parking Area or two pedestrian entry points along the Perimeter Sidewalk.
The Hollow Creek Trail (HCT)
5.0 miles
Woodside’s longest and most scenic trail, the HCT provides a true hiking experience through the Hollow Creek Land Preservation Area (HCLP). The route features wooded terrain, creek crossings, and lake views. Highlights include the Anderson Pond Dam, fishing platform, and scenic outlooks. The trail begins and ends at the Trailhead Parking Area and can be walked clockwise or counterclockwise.
Mill Road/Azalea Trail Complex
This interconnected system begins at the Trailhead Parking Area and includes the Mill Road, Azalea, and Hollow Creek Trails. Follow the blue blazes to stay on course. The Mill Road Trail runs below the Cunning Lake Dam and follows a stream. The Azalea Trail forms a figure-eight with two connected loops, featuring a bridge over a stream and blooming native azaleas in spring. This fully wooded area offers shade, natural beauty, and options for both easy and challenging walks.