Trekking in Nepal up to Dharamsala in September

I am scheduled to land in New Delhi on September 17th for my first trip to India for 4-5 months!! I want to trek in Nepal while the weather is nice and have to be in Dharamsala by the end of September (27th) that leaves 10 days to get from Delhi to Dharamsala. Where do i begin the trek? I am mid 30s fit and traveling with fit male. Medium budget, I wouldn't be able to trek due to yoga and other engagements until mid November....so that's the only chance to go to Nepal....any suggestions??

Our first time to India, but I am a versed traveler...my male friend, not so much. Do I need to schedule a private trek? Schedule when I get there? Get a ticket from Delhi to where?? Please help!!

CA note: I'm thoroughly confused by your post. Given below are some questions that should clarify and help IMers suggest something:

a) When do you have to go to Nepal. Dates (I gather mid november but what until then?)
b) Nepal is nowhere close to Dharamsala. Dharamsala is in HP. Assume you have to come back to Delhi. When?
c) Are you seriously planning to Hike upto dharamsala from delhi? Not that it's not doable, just might be boring / near highways.

.... that's about all the logic i can throw in at this point of time.

- Vaibhav

Thank you! I suppose it makes more sense in my head.
1. I arrive in Delhi on Sept 16 - was wanting to go to Nepal right after then possibly?
2. I realize it is nowhere close, but is there any point of entry/exit that would make more sense than Delhi- Kathmandu - trek back to Kathmandu- back to delhi - up to dharamsala by the 27th of September? that wouldn't leave much time for trekking
3. highways are not interesting me at the moment - I have plenty of those in the US

Plan on attending teachings in Dharamsala - then go to Rishikesh for a yoga training until Nov 8 - isn't it too cold to trek in Nepal after that??

Thank you so much for your time and sorry about confusion - first time here

If you leave India & go to nepal you won't be allowed back into India for 2mths. You could go trekking near d'sala or other area's of HP. Or you could fly straight to Nepal then India.KK

Is this being enforced? Or is there a multiple entry exception I can get?? I have heard mixed things about this 2 month rule.

Sidestepping the visa question (doesnt apply to me), quick comments:

a) Yes, it will be cold in Nepal in November. Late september should be fine after the monsoon has receded.

b) There's a border crossing - see this forum for details: http://www.indiamike.com/india/crossing-the-border-f57/. but given your timeframe (you'd like to trek inside nepal and get in and out of Nepal in the September 17-27 window), the only possibility is flying.

Thank you so much!! I will plan on flying in to Kathmandu and taking it from there. Thank you thank you!!