Meet Jack Staines, a "Black Jack" in Historic Old Portsmouth

Step onto Portsmouth’s waterfront in Portsmouth, New Hampshire, and you enter a working harbor where wooden piers, brick streets, and the low roar of tides form a backdrop to stories seldom heard on standard history walks. Meet Jack Staines, a “Black Jack” whose life illuminates the complicated seam between captivity and freedom that Black mariners navigated from 1740–1865. This 90-minute walking tour, led by Sankofa Scholar & tour guide Garrett Walker, traces those paths between ship decks and shore, revealing how the sea offered both danger and opportunity.

The route threads historic streets and the harbor edge, where sailors once loaded cargo and pressed men into service, where others found wages, travel, and a degree of autonomy beyond land’s restrictions. Key features include the waterfront itself, winding cobbles and wharves, and views into the harbor and its tidal channels—natural elements that shaped work rhythms and escape routes. Visitors will hear the story of Ona Judge Staines, whose escape from enslavement connected intimately to Jack’s story, situating personal courage inside larger maritime networks.

What sets this tour apart is its focus: not on ships or captains alone, but on Black mariners as active agents—navigators, laborers, and risk-takers whose choices altered families and communities. Small group size (max 20) keeps the experience intimate; the guide’s scholarship layers local archival detail over physical landmarks. Practical notes: the tour runs rain or shine, departs from the operator’s office at 2:00 p.m., and asks guests to arrive ten minutes early.

Tickets are final sale; organizers will reschedule or refund only if they cancel for safety or illness. Expect the walk to be conversational and evidence-driven: documents, maritime contracts, and residents’ accounts get woven into the stops. Bring a notebook if you want to jot names and sources; the guide often cites archives and points out markers or plaques.

With a maximum of twenty guests the pace stays conversational, allowing questions about labor conditions, routes to freedom, and how maritime law intersected with everyday life for Black sailors today. For visitors, this is a way to see Portsmouth through an alternate lens. The walk highlights the mechanics of maritime life—tidal pulls, stone quays, and narrow alleys—while lifting untold human stories from 18th- and 19th-century records.

It’s recommended for history lovers, families with older children, and anyone curious about how labor, law, and the Atlantic shaped opportunity and risk. The tour contributes to a fuller public memory of Portsmouth, widening the interpretive map beyond grand houses to working waterfronts and the people who kept them moving. Whether you’re on a weekend escape or a longer stay in the Seacoast region, this walking tour provides a compact, powerful primer on maritime freedom and the human cost behind it.