Arrive in New Delhi, India. Delhi is home to the region's largest international airport. Spend the night here (most likely you've arrived in the middle of the night anyway)--you've got a long day ahead. Round-trip economy tickets from New York to Delhi usually run between $850 and $1,500.
If you have the money, catch a plane to Siliguri. The plane option typically costs around $250 and takes about 4 hours before landing just outside of Siliguri in a town called Bagh Dogra. You can purchase your tickets online or at the domestic airport, right next to the international airport at which you recently landed.
If you are more of a budget traveler, catch a train. The train option takes about 20 hours, costs anywhere between several dollars and over $100 (depending on the type of seat you purchase), but takes you straight to Siliguri. You can buy train tickets at the central train station in Delhi; any cab driver can take you there.
Find a shared jeep bound for Kalimpong. If you traveled by plane to Bagh Dogra, shared jeeps and taxis are waiting outside of the arrival terminal. Typically these costs you between 1,000 and 2,000 rupees to get you all the way to your destination. If you traveled by train to Siliguri, find a taxi or a jeep outside of the train station. The price will be about the same, perhaps a few hundred rupees less.
Drive to Kalimpong. This generally takes between 2 and 3 hours. You'll head across the open plain, into the jungle and up the windy roads that climb the mountains and descend the valleys until you reach Kalimpong. It's an amazing ride!
Enjoy the foothill town of Kalimpong. Don't miss out on the town's several monasteries, its flower gardens,and its incredible views of the high Himalayas, including Kanchenjunga--the world's third-highest mountain. Opportunities for day hikes are also plentiful in and around Kalimpong.
