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Is there ever any way, in any chapter, to cross the region from Wyke to Highcastle, or vice versa?
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UndeadHalfOrc: Is there ever any way, in any chapter, to cross the region from Wyke to Highcastle, or vice versa?
Not really. The whole northern side of the mountains is accessible only in Chapter 4 and you both arrive and leave without travelling 'on road', so to speak.