The best walks and hikes around Bradford West Gwillimbury

Cookstown is a small town that the Trans-Canada Trail runs through, built over the 1858 Grand Trunk Railway bed. There are a few family restaurants and chain restaurants in Cookstown, a few shops and antique markets. Some visitors come just for the antique market scene.

The Trans-Canada Trail, in total, stretches over 28,000 kilometers across Canada and stands as the longest recreational, multi-use trail network in the world. This section is unpaved with a gentle change in elevation, passing though clumps of forest, small towns and open farmland.

Thornton was a small town developed during the 1820s, on flat farmland. The Trans Canada Trail runs through the heart of the town, with a handful of family-owned restaurants, and, of course, a Tim Hortons. About 1000 residents call Thornton home.

Spanning more than 13,000 hectares across multiple tracts throughout the county, Simcoe County Forest is one of the largest municipal forests in Ontario, protecting a diverse mix of pine plantations, hardwood forest, wetlands, and other natural areas. Established through large-scale reforestation efforts beginning in the 1920s, the forest now includes an extensive network of trails popular for hiking, trail running, mountain biking and other outdoor activities. While each tract has its own character, the forest as a whole is a patchwork of natural areas that preserve green space and wildlife habitat across much of Simcoe County.

The Hodgson Tract is part of the Simcoe County Forest, and includes a network of trails that wind through mixed forest and regenerating woodland. Popular with hikers, trail runners, mountain bikers, and horseback riders, the trails range from wide forest roads to narrower singletrack paths, with some sections that include steeper climbs and descents. These sections are especially popular for mountain biking, so keep an eye out for riders as you explore the trails. The tract sits relatively close to Highway 400, but the forest setting still makes the trails feel secluded, with long stretches of wooded paths and few signs of the surrounding urban area.

This trailhead also includes a small parking area that sits right off 11th Line, and provides access to the Hodgson Tract and its extensive network of forest trails. From here, you'll quickly enter the mixed woodland, with plenty of winding singletrack routes that extend throughout the tract. Parking and access to the trails are free, making it an ideal starting point for exploring one of the county’s most popular forest recreation areas.

This small pond is home to a variety of birds, especially ducks, and plenty of small fish, making it a fun spot to bring kids. The trails aren’t paved but are still easy to walk and bike-friendly. A short path leads out toward the middle of the pond, giving you a close look at the little ecosystem that forms around this quiet stretch of water.

Peggy’s Wood Tract is a forested loop with a mix of conifer stands, soft earth paths, and short stretches of gravel. The trail feels surprisingly natural for such an urban spot, with rooty sections, a few muddy patches, and the occasional fallen log to step over. It isn’t heavily signed, so having a map helps, especially at the smaller junctions. Despite being close to town, the woods stay peaceful, and you’ll often spot birds or small wildlife along the way. It’s a beautiful place to walk in any season, especially in the fall.