The track was built in 1958 at the intersection of Illinois Route 31 and Huntley Road, north of Carpentersville — at the time a small industrial town on the Fox River that was beginning to experience post-war suburban growth. The developer behind it, Besinger, was erecting a housing subdivision along the river and conceived the road course as an attraction across the highway from the new homes.
As originally configured, Meadowdale measured 3.27 miles (5.26 km). Its most distinctive feature was a steep 180-degree curve known as the Monza Wall, which swept cars onto a three-quarter-mile front straight. The circuit was designed on European road-racing principles, with cambered corners and minimal run-off — a philosophy that would define both its appeal and its problems throughout its existence.
The Chicago Region of the Sports Car Club of America (SCCA) conducted the track's inaugural event on September 13–14, 1958, a regional race that drew an estimated 150,000 spectators. Despite the impressive crowd, the opening weekend was troubled from the start. Grass seeding had not been completed, and dust clouds engulfed the circuit and its surroundings throughout the weekend. The paving on the Monza Wall was rough; run-off areas were minimal and ended abruptly at bridges set at dangerous angles to the track. A fatal accident during the third race further damaged the event's reputation before the circuit had established itself.
Following the inaugural meeting, SCCA entered a long series of negotiations with track management over required safety improvements. Dissatisfied with the pace of change, the organization scheduled no events at Meadowdale during 1959 or 1960.
Despite the difficult opening, Meadowdale hosted a variety of motorsport disciplines across its operational life. SCCA regional and national events returned to the circuit after the initial hiatus. The track also hosted USAC auto racing, AMA motorcycle racing, and kart racing. In addition to sanctioned events, rental days to driving clubs and private groups provided the most reliable source of income for the facility.
The track hosted an SCCA Trans-Am Series race in its final year, on July 7–8, 1968, as a last-ditch effort to secure the circuit's future by attracting major professional competition. The attempt came too late.
Meadowdale's management was never able to secure the funding necessary to complete the safety improvements demanded by SCCA and other sanctioning bodies. The track also faced direct commercial competition from Road America in Elkhart Lake, Wisconsin, a more polished and better-funded circuit that drew entries and spectators away from the Carpentersville venue. The combination of an unshakable "killer" reputation, inadequate facilities, and financial pressure proved fatal. The track ceased major racing operations after the 1968 Trans-Am event and closed in 1969.
Proposals to revive racing at the site surfaced periodically in subsequent decades but foundered on the same obstacles — unsafe conditions and competition from nearby circuits — that had doomed the original venture.
In 1994, a group of local park districts purchased the northern 90 acres (approximately 360,000 m²) of the track's land for a forest preserve, acquiring the remainder of the site in 2002. The area, now known as Raceway Woods, is maintained by the Dundee Township Park District and the Forest Preserve District of Kane County as a nature preserve and recreational area. Volunteers who care for the site have made efforts to retain the original track surface and related structures, and the circuit's heritage is honored through an annual mountain bike race called the Raceway Rally. Engine blocks and other castings from the racing era remain scattered through the preserve, visible to visitors on the trail network.