Distance: 8 miles
Swallow Cliff Woods, a steep bluff area that cuts into Sag Valley near Chicago, provides direct access to an 800-acre preserve full of hilly, forested trails. From the north entrance, you’ll climb 125 limestone stairs up to a short connector trail that eventually splits off into brown and yellow tracks. Go for the yellow, which runs about eight miles extending west to Cap Sauers Holding Nature Preserve and east to Palos Park Preserve. You’ll cruise through wetlands, prairies, and meadows, and if you’re lucky, you’ll hear the park’s songbirds. The best part? It’s open year round, so snow shouldn’t stop you from getting in your workouts.