Rohru - Chakrata around 7-8 hours. Its not difficult but challenging

Chakrata will be a bit off the route if you wanna do rishikesh. For that you would have to follow this route i.e. Tiuni-Naugaon-Vikasnagar-Haridwar-Rishikesh. So i would suggest stick to Chakrata only.
I did it the other way round via chandigarh. But my motive was just to enjoy the ride and the journey, rather than the destination. 3 days would be sufficient, but not enuf if you want to explore rohru
You could follow this itenarary if it suits you(ex chandigarh):
Day 1: Chandigarh - Shimla - Rohru (220 kms)
Day 2: Rohru - Tiuni - Chakrata (~125 kms)
Day 3: Chakrata - Poanta - Chandigarh(205 kms)
Quite poss



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