Jay:
try
LOCKE'S HILL, specifically, the Lakeview Trail.....only .7 of a mile and great views!
http://forum.hike-nh.com/viewtopic.php?t=3788
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Went on a great hike today with my wife and our 3 1/2 yr old. Locke's Hill in Gilford, NH is a great first hike or with little ones. Our 3 1/2 yr old did this hike on her own( was her first hike also). We parked off rte 11 by the scenic view( there's signs for the parking lot) and grabbed a map out of the green mailbox and started up the Quarry trail. Some wet areas but real nice. Not too hard of a climb. Follow the Blue marks on the trees.
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WINNI FORUM COMMENTS....
PS - I don't think you are going to get a stroller up there but at only .7 of a mile the little rugrat can walk or be carried. don't forget to bring your lunch along and enjoy the stone chairs!