On the way to Shimla, you will pass Yadavindra Gardens, also known as Pinjore Gardens. The sprawling garden complex was built as a retreat for Mughal Emperor Aurangazeb and is a perfect place for a quick chai break. However, Giani Dhaba at Dharampur (50 km further) is a better pit-stop, and quite a popular one too.
A left turn at Dharampur will take you to the little hilly town of Kasauli. If you take this 10 km detour, make sure to swing by the Kasauli Brewery and visit the beautiful New England Church.
Another highlight on the NH5 is the Timber Trail Resort. The resort allows visitors to take a trolley ride to the gorgeous mountain range that runs alongside all the way to Shimla. Located a little before Shimla is the Tara Devi Mandir, a 5 km detour from NH 5. The temple is at 1851 metres above the sea level, and offers a stunning view of the surrounding valley.
NH5 is a mostly convenient highway to drive on, though trucks can be a bit of a nuisance on hilly sections. We advise extreme caution, especially in the face of state buses - their sure-footed driving is often borderline dangerous.