March to June and September to November are the best months to do the Delhi to Dehradun trip. The weather is pleasant with temperatures ranging from 15°C to 30°C making the drive comfortable. Monsoon from July to August should be avoided as heavy rains can cause waterlogging in low lying areas around Saharanpur and Muzaffarnagar and can cause traffic disruptions.
Winters from December to February are also good to visit especially if you love cold weather as Dehradun becomes a misty paradise. How