Ready to hit the trails? From wooded ridges to lakeside paths, here are the top 12 year-round hiking locations throughout the Commonwealth of Massachusetts.
1. Mount Wachusett (Princeton, MA)
At 2,006 feet, Mount Wachusett is the tallest peak east of the Connecticut River. With 17 miles of trails, hikers can choose from gentle woods walks to steep summit climbs.
Difficulty: Moderate
Trailhead: 345 Mountain Road, Princeton, MA
2. Mount Watatic (Ashburnham/Ashby, MA)
A beloved 1.1-mile climb to the 1,832-foot summit, offering sweeping views and a short spur to Nutting Hill.
Difficulty: Moderate
Trailhead: 248 Massachusetts Ave, Ashburnham, MA
3. Leominster State Forest – Crow Hill & Monoosnoc Trails (Leominster/Westminster, MA)
A 4,300-acre forest with pond loops, rocky cliffs, and a long ridgeline leading to Sholan Farms.
Difficulty: Easy to Moderate
Trailhead: 80 Fitchburg Road (Route 31), Westminster, MA
4. Purgatory Chasm (Sutton, MA)
A dramatic granite gorge with boulder scrambles, caves, and rugged terrain. Rim trails offer easier options.
Difficulty: Moderate in the chasm, Easy on rim trails
Trailhead: 198 Purgatory Road, Sutton, MA
5. Winnekenni Park & Kenoza Lake (Haverhill, MA)
A 700-acre natural area with 9.5 miles of lakeside and wooded trails leading to Winnekenni Castle.
Difficulty: Easy
Trailhead: 347 Kenoza Avenue, Haverhill, MA
6. Harold Parker State Forest (Andover/North Andover, MA)
A massive 3,294-acre forest with 56 miles of trails around 11 ponds, suitable for hiking, biking, and skiing.
Difficulty: Easy to Moderate
Trailhead: 305 Middleton Road, North Andover, MA
7. Moore State Park (Paxton, MA)
A scenic 400-acre park with waterfalls, mill ruins, and flat, family-friendly walking paths.
Difficulty: Easy
Trailhead: 1 Sawmill Road, Paxton, MA
8. Jewell Hill (Ashburnham/Ashby, MA)
A Trustees property featuring meadows, woodlands, and a hilltop overlook with distant skyline views.
Difficulty: Easy to Moderate
Trailhead: 232 Crocker Road, Ashburnham, MA
9. Doyle Community Park (Leominster, MA)
A 157-acre former estate with gardens, forested paths, and ADA-accessible trails.
Difficulty: Easy
Trailhead: 464 Abbott Avenue, Leominster, MA
10. Burncoat Pond Wildlife Sanctuary (Spencer/Leicester, MA)
A Mass Audubon sanctuary with wooded trails, wetlands, and quiet pond views.
Difficulty: Easy to Moderate
Trailhead: 229 Greenville Street, Spencer, MA
11. Burncoat Park (Leicester, MA)
A 115-acre conservation area with easy forest loops and pond access.
Difficulty: Easy
Trailhead: 70 Royce Road, Leicester, MA
12. Ward Reservation (Andover/North Andover, MA)
Features Holt Hill—the highest point in Essex County—and the Solstice Stones with sweeping views.
Difficulty: Easy to Moderate
Trailhead: 65 Prospect Road, Andover, MA
Directions: All trailheads above include direct street addresses or standard GPS entry points. For detailed maps, consult DCR, The Trustees, or Mass Audubon.
