Boston Rocks Guidebook has a great section on Crow Hill, as does Stewart Green's Rock Climbing New England Falcon guide. The Falcon guide also covers Rose ledge
The local guides are usually superior to the Falcon ones - especially the Falcon ones that were written by an outsider after a quick superficial tour of the area. Al's Rose guide and Larry/Richard/Susan's Boston Rocks guide were written by long time active locals well versed in the areas who spent an incredible amount of time and effort writing them.
red rocks (gloucester (cape ann)) would be an easy mellow place to practice trad... Not sure how motivated you are to come that far for a few mellow cracks and a few tricky slabs though.
if you're in western mass I would recommend farley. there are many trad lines, mixed lines and sport. there is no guidebook though, so find someone who knows it a little bit
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