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Yes actually geographically u can and there are some epuc treks that starts from utrakhand and ends at himachal.
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Yes.. but needs good planning
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There are some High mountains passes which connects uttarakhand to himachal but they are difficult ...by road you can reach from Paonta Sahib and tyuni
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Rupin Pass Borasu Pass
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Yes, u can, but study the maps well
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Yes, its possible. The roads are good as well. Would be probably around 250-300 kms
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Yes you can
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