Operation MARKET-GARDEN had two major objectives: to get Allied troops across the Rhine and to capture airborne divisions, to drop in the vicinity of Grave, Nijmegen, and Arnhem to seize bridges over several canals and the Maas, Waal (Rhine), and Neder Rijn Rivers. They were to open a corridor more than fifty miles long leading from Eindhoven northward to Arnhem. Operation GARDEN, called for ground troops of the ninety-nine miles. The main effort of the ground attack was to be made by the British XXX Corps. On either flank the British VIII and XII Corps were to launch supporting attacks.
The 101st Airborne Division was responsible for a 15-mile segment road of narrow concrete and macadam ribbon stretching northward and northeastward from Eindhoven in the direction of Grave. The men of the 101st would soon call that segment of road the nickname Hell’s Highway. The objectives vital for subsequent passage of the British XXX Corps were located at intervals along the entire 15-mile stretch of road. The division commander, Maj. Gen. Maxwell D. Taylor, later compared the situation to the early American West, where small garrisons had to contend with sudden Indian attacks at any point along great stretches of vital railroad.
Recalling dispersion that had plagued the division in Normandy, General Taylor insisted upon drop zones fairly close together, no matter how scattered the objectives. Two regimental drop zones and the division landing zone were located near the center of the Division sector, west of Hell's Highway in a triangle marked by the villages of Zon, St. Oedenrode, and Best. The 501st PIR, commanded by Col. Howard R. Johnson, would drop to the north of the other regiments near Veghel onto Drop Zone “A” in order to seize rail and road bridges over the Willems Canal and the Aa River. Gen Taylor ordered the 506th PIR, commanded by Col. Robert F. Sink, to drop close to Zon onto Drop Zone “C”, secure the highway bridge over the Wilhelmina Canal a few hundred yards south of Zon, and then march south on Eindhoven. Gen. Taylor tasked the 502nd PIR, commanded by Col. John H. Invasion from the Sky Michaelis, to land just north of the 506th onto Drop Zone “B”, guard both drop zones and secure Landing Zone “W” for gliders, and to capture the road bridge over the Dommel River at St. Oedenrode. Additionally, General Taylor tasked the 502nd to secure bridges over the Wilhelmina Canal south of Best, four miles from Zon off the west flank of Hell's Highway in order to strengthen the over-all position of the 101st. In order to meet Gen. Taylor’s intent, Col. Michaelis sent a company to these bridges.
Beginning three minutes after H-Hour, at 1303, men and equipment began to descend upon the parachute and glider landing zones. Despite flak and small arms fire, only one Pathfinder plane and two of the other parachute aircraft of the 101st Airborne Division failed to reach the drop zones, although some planes went down after the paratroopers had jumped. Incurring casualties of less than two percent in personnel and five percent in equipment. In an hour and one half 6,769 men were on the ground. Only 1st Battalion, 501st PIR and 1st Battalion, 502nd PIR failed drop on their planned drop zones. The mission called for the entire 502nd PIR to drop on Drop Zone “B” which was the northernmost of the two drop zones between Zon and St. Oedenrode; 1st Battalion commanded by Lt. Col. Patrick Cassidy, came down two miles away on the neighboring drop zone. Although delayed by this misadventure, by nightfall had brought a persistent bunch of rear echelon Germans to heel in St. Oedenrode and thereby secured both a main highway and an alternate bridge over the Dommel River. After deploying troopers to defend the village, Lt. Col. Cassidy sent a patrol northeast along Hell's Highway which contacted the 501st Parachute Infantry at Veghel.