Rajpur Road runs about nine kilometres from the Clock Tower to Rajpur village, where the old bridle path to Mussoorie begins. It is the city’s main street, its café strip and, for most of its length, a gentle climb. Start early and walk north.
The busy stretch
The first two kilometres are showrooms, banks and bakeries. Stop for rusks or cheese straws, then keep going. Traffic thins out after Dilaram Chowk.
Bungalows and kitchens
The middle of the road is where Dehradun still looks like old Dehradun: deep verandas, tall trees and gates with brass name plates. Tibetan kitchens and small cafés sit between them.
The road climbs gently the whole way, so the walk back down is the easy part.
The finish
At Rajpur the road narrows and the hills close in. Have a last chai, then take a shared cab back down.
Local tip · Walk on a weekday morning. Weekend afternoons bring heavy traffic to the lower half.