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County: Madison, IL
Route 66 had to cross the Mississippi somewhere. It could just never quite make up its mind where.
Even long before the Gateway Arch would tower over the skyline, the logical crossing for the Mother Road was downtown, leaving the largest city of the Metro East, East Saint Louis, for the biggest the road would see until Los 
Angeles: Saint Louis, Missouri. And this is where the road did originally jump the Mississippi...at least until 1936 when.
Route 66 headed into the Metro East from Hamel and Edwardsville, turning left through Mitchell and then, within several miles of the river, making a sharp turn south to head through Granite City and Venice en route to East St. Louis and sights beyond. With the completion of the Chain of Rocks Bridge to the north of the city, traffic began to flow across the river far from the growing congestion of downtown, and in 1936 the Mother Road dropped its southbound trip through the Prairie State and stepped across the river at the very north border of the City of Saint Louis. (For 
a complete summary and chronology of the various Mississippi River crossings of Route 66 check out the Bridges section.)
At just over a mile in length, the Chain of Rocks Bridge was erected in 1929 at a cost of between two and three millions dollars by private investors who later sold the bridge to the City of Madison, Illinois in 1939. For most of the structure's operation it was a toll bridge, originally a five cent charge that evolved upwards until Madison was forced to stop charging a fee after bonds on the bridge were paid off. It was built over an area of the Mississippi that had been dubbed "Chain of Rocks" after a seventeen mile series of rocks that produced wild white rapids and a great danger for traveling vessels; this hazard was bypassed in 1953 with the eight mile long Chain of Rocks Canal on the Illinois side that gave Route 66 yet another brief waterway to cross, forcing the highway to venture slightly to the south sooner than in its original alignment.
The bridge's most recognizable quirk was easily the 22 degree turn that it takes about halfway across the river. Stories abound that different pieces of land were purchased on either side of the Mississippi, forcing the span to bend and head towards a different landing point on the other shore. The accepted truth, though, is that ships needed a way to navigate through the bridge's supports and around the two City of Saint Louis intake valves on the side of the bridge, but there were only certain places on the Illinois side of the river with firm enough footing to fully support the bridge. Thus the bend, which allowed for strong anchoring on both sides of the river and safe passage for boats before the construction of the Chain of Rocks Canal several decades into the bridge's lifespan.
The bridge was originally to be constructed with a forty foot width, allowing ample room for a two-lane highway, but travelers were instead greeted with a twenty-four foot clearance from curb-to-curb, an especially precarious limitation at the bridge's signature bend. While driving at slow speeds to avoid bridge-closing collisions those motoring Route 66 could observe two beautiful, classically built water intake towers to the south of the bridge that date back to 1894 and help provide Saint Louis with much of its drinking water.
Back in the heyday of the Chain of Rocks Bridge, the west shore was an exciting place for travelers, particularly the young ones. Along with the tollbooth (excitement!), visitors were greeted with the sight of Fun Fair Park, an amusement park that for several decades operated just to the south of the bridge on the Missouri side. No relics of the park remain today; the Show Me State shore is rather barren other than a small parking lot for those who wish to walk or bike the mile span. While the west side of the riverbank now offers very little to the contemporary Route 66 traveler, the eastbound roads still feature a few items of interest: along with the Luna Cafe and Bel-Air Drive In sign in nearby Mitchell, two older motels line the Chain of Rocks Road several miles before the bridge's Illinois footprint. An old gas station sign and another travel court greets motorists on the west side of Illinois 3 on the final approach.
In 1967 the New Chain of Rocks Bridge opened to the north, carrying four lanes of Interstate 270 across the Mississippi, and the old bridge was closed for good. The City of Madison looked to sell the bridge for scrap, but when the cost of demolition promised to exceed any potential revenue they allowed the structure to just sit and rot. It was used briefly in the filming of the 1981 movie "Escape from New York," but after that it would be sixteen years before Trailnet, a Saint Louis area organization aimed at improving biking and walking trails, made an arrangement with the city to open the span for pedestrian and bike traffic. The bridge was cleaned up, the state line was marked with shields on each side and pink spray paint at the exact boundary, several benches were placed along the way, and new blue guardrails were installed on the sides. A few Route 66 themed exhibits were also featured on the Missouri side of the span, including several informational boards, replicas of motel and service station signs and a model of an old firetruck. Recently restrooms were also installed at the foot of the bridge where the bike trail approaches the structure after traveling along the Missouri shoreline. Due to the unsafe nature of the area (a double-murder was committed on the bridge in 1991, and the areas leading up to the bridge - especially on the Illinois side - are known to be dangerous) the bridge is only open certain times of year, and though Trailnet attempts to keep the Missouri parking lot staffed at times, with a small fee for ensuring your car's safety, low funding keeps the bridge from being utilized to its utmost potential.
Route 66 followed Chain of Rocks Road west out of Edwardsville before angling to the south to cross the Chain of Rocks Bridge. Originally the road took a hard left close to the river, but with the construction of the Chain of Rocks Canal in 1953 it began to angle south more gradually a bit further to the east. The bridge, and the Chain of Rocks Road approach, was always a two-lane alignment, with the later four-lane Route 66 following the corridor of Interstate 55 into the Metro East through Collinsville. For a complete summary and chronology of the various Mississippi River crossings of Route 66 check out the Bridges section.
