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Hopkinton Area Land Trust A Taste of Winter If youre a crosscountry skier or snowshoer the best place to do it is at the Fruit StreetPratt Farm complex. For the beginner skier there are perfectly flat trails at Pratt Farm and for snowshoeing and more advanced skiing there are gently rolling woods trails with a couple of steep spots on the Fruit Street trails. Keep a lookout for ski bypasses on the steepest sections. But you have to get out there right after it snows because great conditions dont last long.