Sandy Point State Reservation is a 3.4 mile loop trail located near Ipswich, MA and is good for all skill levels. The trail is primarily used for hiking and walking and is accessible year-round.
Unfortunate that they block cars from going in if the parking at the beach is full. I walked 10 miles back and forth and still felt like I didn't get to see much. A lot of walking on pavement. Not worth it unless you can drive a little further out.