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Scenic route from Sheffield to Easton, NJ?

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What would be the best route from the Berkshire Hills to Easton? We need to go on a fairly direct route and wondered if the Delaware gap offers tourist possibilities - short hikes and a place to stay. What is Harriman SP like? Would we be able to travel from Bridgeport to Long Island by ferry, with a car and explore east of NY? Long Island looks rather urban so where are the most scenic bits? We shall be there mid June.

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