Cotton Valley trail...
..is more of a walk than a hike but, at 6 miles one way, it travels from downtown Wolfeboro, passes by a lot of history, a few beaches with time to dip the toes in the water and lots of flowers now. Ran it this morning and passed more Lady Slippers than I have ever seen in one place.
Crushed stone/dirt and flat the whole way.
You could also hike up the Castle in the Clouds road or check out the Bearcamp River (Beede Falls) in Sandwich off of Sandwich Notch Road (You would be near the Sandwich Creamery afterwards as well!)
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