There should be several choices. I live at the bottom of a 1200’ hill so you could just drive up there. You can hike up the access road to South Pack (Miller State Park) and that’s 2290’. Across the road, Temple Mountain is 2044’. In Bennington, Crotched is 2064’. The Crotched Mountain Rehab Center in Greenfield is close to the same height and you can also drive to the top there. There’s a couple of hiking trails too.
If you want small mountains, it’s not that far.