Kitzbühel got its city rights from a Bavarian duke in 1271 and belonged to Bavaria until 1504, a border town on the trade road to the south. It was a summer resort first. In the early 1890s the hotel pioneer Franz Reisch skied down the Kitzbüheler Horn (the year is given as both 1892 and 1893), and the town went on to become one of the first winter sports destinations in Austria. The Hahnenkammbahn opened in 1928, the first ski race on the Hahnenkamm was held in 1931, and since 1967 the Hahnenkamm Races have been part of the World Cup, on the Streif, a course the organizers call one of the hardest downhills in the world.
What the Streif doesn't tell you is that Kitzbühel is a small, old and walkable town of 8,284 people, with a pedestrian old town, a church tower of 48 m, a good Alpine painter's museum and a lake you can skate on. It is also low. The ski area runs from about 800 to 2,000 m, and a plan has to be honest about it: snow is made and managed here, the Horn runs for less of the winter than the rest, and the best snow is on the far side at Resterhöhe. That is why this guide has four ski days on four different mountains, and a town day that doesn't need snow at all.
Day one is the Hahnenkamm and the Streif, day two the Fleckalm and Pengelstein side with a toboggan run at night, day three the 3S cable car to Jochberg and Resterhöhe, day four the separate Kitzbüheler Horn, and day five the old town, the museum and the Schwarzsee. Start on a Monday, arriving Sunday evening: the museum is open on Friday afternoon, and the restaurants named here were open on the evenings they are given in autumn, so confirm their winter hours. For the country as a whole see Austria, and for the big cities you may fly into, 5 Days in Innsbruck and 5 Days in Salzburg.