There two ways to reach Dharamshala from kasol, the one you're looking at is via Mandi-Barot-Palampur, I don't know about the present roads condition but there are a few rough patches its twisty winding road, definitely short, the view you get is amazing. The other way is via Mandi-Hamirpur-Kangra, this is a bit longer 7H30min bit the roads are good for driving as they are less twisty and winding wah less than the forst one, the view is good. of you're not comfortable driving or being driven to, in hair pind bends roads for the most part I'd suggest the Hamirpur route. either way there are hotels to stay in Palampur and Hamirpur as well as in Barot. start early in the morning (6-8AM) and then spend the afternoon and evening in places Dharamshala like Tapovan, Nourbulingka Monastery, The Divine Hima, Joyful Cafe, Bakes and brew, HPCA Pavilion, Espresso Bar, and so on. places near Palampur that are worth a look is Andretta for pottery and Shobha Singh Art Gallery, both close at 4 so be a bit early, Bir Billing for paragliding, Barot for trout fishing. Places near Langra are kangra fort and Masoor Rock cut temple worth a look . either way you choose just see these place enroute and your day will be great.