Arrive in New Delhi. India's capital city is home to the region's largest international airport, named after assassinated Indian leader Indira Gandhi. Round-trip economy flights from New York to Delhi usually cost between $850 and $1,500 or more, depending on the carrier and the time of year.
Buy a train ticket to Pathankot. Any cab driver in Delhi will be able to take you to Delhi's central train station. Be sure to arrive around 7:30 or 8:00 in the evening, as trains typically depart for Pathankot soon after 9:00. The ticket will cost anywhere from a few dollars to $80 or more, depending on the level of comfort you desire.
Arrive in Pathankot. The train ride should last about 10 hours, most of which, hopefully, you are able to sleep through.
Find a taxi to take you to Dharamsala. The jeep may present Mcleod Ganj as its destination; Mcleod Ganj and Dharamsala are essentially the same town, so any jeep going to Mcleod Ganj will take you to Dharamsala as well. There are shared jeep taxis, which charge a few dollars for the entire 2 to 3 hour ride, or you can take a private taxi, which will cost you between $20 and $40.
Arrive in Dharamsala and enjoy. The town is a center of Tibetan culture, home to several monasteries, and teeming with Tibetan cultural and political organizations. In addition, there are a variety of good hole-in-the-wall restaurants to choose from, and hotels range in price from extremely budget to luxurious and costly. Take advantage of the day hike opportunities--the local Tourism Bureau (anyone in town can direct you to it) has hiking maps that it hands out for free.