Hey! Its always good to visit a famous hill retreats like Shimla during off season. The weather will be pleasant in the month of October. You can visit places like Jhakoo Temple, Chadwik Falls, take a walk around Indian Institute of Advanced Studies. You can also head to nearby places like Kufri, Shoghi (for some offbeat experience) and Mashobra.
Chill at Mall road; go to Jakhoo temple and also if you like trekking; figure out small natural treks around the city. The weather is lovely around that time of the year in shimla. Cheers !
Chadwaick waterfall. Do visit this place as it's beautiful and away from the city.
The Ridge which is the heart of Shimla.
Kufri
Jakhoo Hills - A temple of Hanuman ji. Also the highest peak of Shimla
Mall road and explore some cafes
Mall Road shimla
Jakhoo
Indian institute of Advance study
Scandal Point
Kali Bari temple
Sankat mochan Temple
Take a walk in Kuthar Fort Kufri
Johnnies Wax Museum
Experience the Ride on Toy Train