Does roam have a boastful connotation

No. I think it's more of a wandering, aimless connotation.

Base on my research  john berryman is  a talented scholar driven to write poetry, is best known for transforming his personal suffering into verse. like robert frost and randall jarrell, he loved teaching poetry and felt most at home with literature and the humanities while  bradstreet enjoyed a relatively privileged life in england, but at the age of eighteen she, her husband, and her parents sailed with john winthrop for the puritan settlement at massachusetts bay.