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Yes you can. Triund trek is a great trek for beginners and is properly marked throughout.
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Yes, you can do it without a guide. You will always find people on the trail to tag along with. You can go to the tour operator's shop near Snow Lion Cafe in Mc Leodganj before starting the hike and check if the tents are available at the top.
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Yes, you could. But be extremely careful during this season. The path tends to be slippery, and hence extremely dangerous.
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Yes. There are going to be many people on the trail and you can join anyone if you need company. I would suggest to book a tent on top before if you do not want to carry your own. This can be done at travel offices in McLeod Gunj. Also start early so you reach on top before sunset. Happy Travelling!
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I went to McLeod Ganj, Triund, Dharamasala and Naddi with a group led by https://www.facebook.com/madcapodyssey
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