Like most of Massachusetts, the best time to visit Gloucester is from June till mid-September when the weather is warm, and it is ideal for enjoying a sunny day out on the beach. Further, it is also the best whale watching season. The winters (mid-October to February), as one would expect, are pretty freezing and wet. However, if one wishes to go skiing or hiking, or enjoy the festive vibe, the winters provide some amazingly cheap deals, and one can make the most of their stay in the off-season.
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