Mattabesett Trail, Mattatuck State Forest, Middletown, CT
Along the 215-mile New England Trail that runs through Connecticut and Massachusetts, catch the 5-mile section of the Mattabesett between Route 77 and Route 17 to reach Bluff Head, a promontory from which you can see Long Island Sound and the Coginchaug Valley.
Level: Easy | Distance from Boston: 126 miles
Middletown, CT, 203-457-9253, website.
Good for youngsters