Well strategically, the real question Allied planners faced in 1944 was how to break out of France and into Germany. Most of Belgium had been liberated, as well as the vital port of Antwerp. But there were still two roads (three technically, but the Ardennes route was never considered) into Germany. The first was the southern root, where an attack out of French Alsace-Lorraine pushed East across the, then North towards Rhine River Valley. The RRV was the heart of German industrial production, and was key to its war effort. The other route was the northbound route out of Belgium, through Holland, into the northern RRV.

The Southern Route was advocated by Patton and his 3rd Army, which was racing towards the Rhine River. Patton felt that he could quickly barrel over the river, smash the German defenders, and capture the RRV. However, the German side of the River was defended by the prewar fortifications known as the "Siegfried" line, which was similar to but smaller than the Maginot line.

Montgomery felt that the northern route would avoid the Siegfried defenses, and would thus be quicker. His view was ultimately adopted by SHAEF and Eisenhower for a lot of reasons. If you watch the movie Patton, from his perspective "Monty" used his influence as a the chief British General to get his substandard plan approved. However, there are other reasons. Patton was far from the American supply base of Antwerp and the Normandy Beaches. He was likewise far from the major bases in southern France. Montgomery was closer to Allied supply bases, and to England, the strategic supply base. Further, he faced less resistance than Patton did. The defenses of the Siegfried line seemed potent, and were manned by troops which were not as battered as those in Holland, just routed from France and the Falaise Pocket. His offensive just seemed to have better prospects for success.

Unfortunately, there were a lot of flaws with Montgomery's plan. First of all, the terrain of Belgium was god awful tank country. Belgium is flat, low, and muddy. It features many rivers and streams, few woods, and lots of built up areas. The infrastructure of the country supports the trade out of Antwerp and Brussels, but there is only one major road from Brussels to Amsterdam. That highway was well paved, graded, and maintained. The problem was it crossed several rivers, and to keep it out of the mud it was built much taller it the surrounding countryside. This silhouetted anything which was trying to travel the highway, and it forced anything moving off the highway to descend the hill.

Montgomery's plan called for airborne landings to capture several key bridges between the starting point on the Dutch/Belgian border, up to the city of Arnhem. These airborne forces would have to operate alone for 3-4 days, while the British XXX Corps and its tanks and heavy equipment pushed up the highway. Once XXX Corps secured Arnhem, it would wheel towards the south and push into Germany and the RRV. He expected to encounter only disorganized and shattered German infantry, which lost most of its heavy weapons in the retreat from the Falaise pocket.

This was Montgomery's second mistake. After the capture of Antwerp, Allied forces paused on the Dutch/Belgian border to build up supplies for another offensive, and to allow time for Antwerp to build itself up as a supply port. German paratroopers and infantry used this time to began to construct a sophisticated defense line to protect against an Allied offensive towards Arnhem and the German border. Further, several panzer regiments and two SS Panzergrenadier divisions were moved to Holland, which was seen as a safe place for them to pause and regain their strength. More importantly, they were placed on the flanks of the route that XXX corps planned to take, and around the landing zones for the three airborne divisions.

Ultimate these were the greatest problems with Montgomery's plan. He asked XXX corps drive a large distance in a short time, on an exposed road, and underestimated the resistance it might face. Further, the airborne forces had to perform almost flawlessly, and secure every major bridge, and most secondary bridges.

Without getting into a blow by blow account of the battle (if you want one, pick up a copy of Cornelius Ryan's legendary A Bridge Too Far. Its not the newest, and it has a few accuracy problems, but its by far the most readable account of the battle.) the problems previously talked about made the battle difficult. The airborne forces landed in good order, and quickly moved towards their objectives, but often faced more serious resistance than expected. In Arnhem, the British 1st Airborne Division found itself cut off, disorganized, and out of contact with XXX Corps or other Allied forces. The American divisions (82nd and 101st) secured most of their objectives, including the massive Nijmegen bridge, but secondary bridges were damaged and destroyed by German forces. Those failures were compounded by the stiff resistance XXX Corps faced. It seemed like around every turn, in every copse of trees, or small hamlet or farm, German tanks and AT guns laid in ambush. And every time a British tank was knocked out, it blocked the narrow road which XXX Corps relied on. Further, the Airborne column came under serious counter attacks by German tanks, which threatened the highway and the key bridges the divisions held.

Ultimately, XXX Corps never reached Arnhem. While it linked up with the 82nd and 101st, the British 1st Airborne had to hold out in the city for 6 days before the division finally surrendered, or fled the city. Those stragglers (including a Polish Airborne brigade) reached XXX Corps as it stood just a few miles south of city, battered and exhausted.

Without the bridge in Arnhem, Montgomery's plan fell apart. XXX Corps was exhausted and unable to continue its offensive. It would have to be rotated to the rear and swapped out with another unit if Montgommery was to continue his attack. And any future attack would be into the teeth of an SS Corps, which Allied forces now knew. Further, by late September the weather was getting worse. The forces had to be rebuilt, and wait for spring.

This time allowed the Allies to build up Patton's strategy. Battle of the Bulge aside, the winter was utilized to build up supplies for an offensive across the Rhine and into the heart of Germany, the RRV.