Travel into Shimla
The best option is to fly to Chandigarh, landing before noon and hire a car. Shimla is ~115 kms away and the drive takes about 3 to 4 hours. I got caught in a traffic jam at the entry to Shimla town-a normal 15-minute drive took over an hour.
Another good option is to take the toy train – it can take ~5 hours but the scenery is great. Kalka-Shimla narrow gauge line was opened in 1903 and today, few trains run on this line daily.
For travel to nearby areas, best to engage a taxi. I don’t find the public or private buses very comfortable.
Shimla also has an airport located about 22kms away. You can check if there are any scheduled flights. I did not find any.
When to visit
The weather has surely changed over the years. In the summer months, temperatures sometimes go above 30 degrees Celsius though evenings are pleasant. It also rains heavily during the monsoon season-June to September with July and August receiving relatively more rains. The winter months, say from October to March are very nice with temperatures below twenty degrees Celsius.
During winters, there is snowfall in nearby areas like Chail and Kufri, but not always in Shimla. Bit unfortunate but the locals confirmed that it rarely snows in Shimla. After several years, it snowed heavily in Shimla in 2018 and also in 2019. So don’t get carried away by the photos of Shimla carpeted with layers of snow every winter.
Also, Shimla does get crowded, in both summers and winters. But relatively, winters are better. But whenever there is snowfall, hordes of tourists are certain to land in Shimla.
Accommodation
Plenty of choices. So take your pick as per your budget. But as much as possible, do stay in a hotel which is walking distance to Mall road. And remember there could be ups and downs along the route and hence even a 2 km stretch can seem long. Some hotels offer complementary drop but you may still have to walk one way.
Another option could be resorts/hotels within say 20-25kms radius and drive to Shimla when needed. There are few very good options though that would reduce your restaurant options(I would not recommend driving after dark on the hilly roads) and will likely be more expensive.
Traffic jams
More common than you can imagine. Our driver was saying that local taxi drivers never break the lane discipline but tourists don’t care. The mountain roads are generally narrow with less than 2 lanes and hence, one should never jump the queue. But amazingly, whenever there is a jam, volunteers appear from nowhere and help in flow of traffic.