Route: Skokie Valley Trail (Lake County, IL)

From TrailLink.com:

An excellent example of land use in greater Chicago, the entire Skokie Valley Trail corridor is a rail-with-trail, paralleled by double tracks that sit about 40 feet to the west of the trail surface. The well-maintained asphalt path offers a nice, smooth experience for a multitude of uses. In addition, the trail shares right-of-way with a major electricity service company, and you will see high-voltage electrical wires overhead.

The trail connects Highland Park in the south to the northern trailhead in Lake Bluff. Although there is no parking or proper trailhead in Highland Park, you can park less than 0.25 mile to the south at the Village Square at Northbrook, a large shopping mall off Skokie Boulevard.

It's amazing to see how nature can flourish in such an urban environment. Even as you pass suburban Chicago life along each side of the corridor, it's not uncommon to come across rabbits, deer, blackbirds, hawks and robins among numerous tree and low-brush species. The trail is sandwiched between US 41 and the train tracks for most of its course, and there are several major road crossings. While these are well marked and include crosswalks, use caution when crossing.

The 200-plus-foot trail bridge over State Route 22 signals the midpoint of the trip. The remainder of the trail passes through mainly commercial and light industrial developments, and, as you approach Lake Bluff, some residential subdivisions. Just after you reach the Deerpath golf course in Lake Forest, the Skokie Valley Trail splits, with a short spur turning east toward the lake and ending at the Laurel Avenue trailhead.

The main trail carries on north another 1.45 miles, still paralleling US 41, to its terminus at State Route 176/Rockland Road. You'll pass through a tunnel under the train tracks just north of Laurel Avenue. At SR 176/Rockland Road, the trail connects to the North Shore Bike Path, which runs east–west along Rockland Road. Turn left on the trail and you can access the Des Plaines River Trail near Libertyville; turn right on the trail to join the Robert McClory Bike Path, which heads north into Wisconsin and south back towards Chicago.