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Both are good options
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Both the options are equally beautiful and doable in October . Depends upon which places your family wants to visit.
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2nd option is better as per my point of view...
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2nd option is recommended based on my experience. It's a different world in Dharmashala
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With family both are equally good options. If this is solo or more of trek like trip I would have said option 2
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I personally like Dharamshala belt.. It will be quite relaxing..
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I would like to suggest the second one..less crowded please than simla Manali trail..
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Dalhousie-Khajjar-Dharamshala
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I would suggest squeeze in 2 more days and add manali to the second circuit.
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