On the waterfront patio of the Harbor Restaurant and Bar, while all manner of yachts floated by, diners in swimsuits chatted happily and passed around a live parrot. Reggae music wafted from the restaurant’s outdoor tiki bar, and when the dreadlocked barkeep took an order (“two caipirinhas, please”), he answered with a Jamaican accent: “Nine dollars.” A little boy sprinted along the docks of a nearby marina and a family of ducks waddled by, their placid presence disrupted only when a waitress dropped two plates of jerk chicken.
This is no Caribbean postcard, nor does the Harbor resemble a pedestrian theme restaurant. The watering hole is sandwiched between campgrounds and situated in an unkempt suburban-style tract house on the edge of the Mississippi River’s Trenton Island—technically in Hager City, Wisconsin, but just across the river from Red Wing, Minnesota. One can spot the Harbor while standing on Red Wing’s historic downtown strip. On clear summer days, an unexpectedly festive scene peeks out between brick buildings. A multi-colored mess of people fans out across the island’s lawn, flanked by Trenton’s most visible feature—a huge and fairly ugly yellow and black sign that reads “Harbor Bar.”
Even from a distant vantage, it’s obvious that the island is the antithesis of manicured Red Wing. Trenton has long been a lightning-rod for area crime and other bad behavior. During the nineteenth and twentieth centuries, it was a noted haven for hookers and moonshiners. Legendary thugs such as Jesse James, Al Capone, and John Dillinger are said to have frequented the locale. “These streets on the island here were some of the most notorious streets in the country—worse than the streets of Chicago,” said Brad Smith, the bar’s scruffy, forty-eight-year-old owner, patting the shellacked surface of his tiki bar.
Indeed, a stranger’s first impression of the Harbor Bar is not of an island paradise, but of a scrappy roadhouse. Passing through the Harbor’s main entrance, one enters a dark, cavernous room populated by biker dudes and throbbing with classic rock. A visitor must hike across the vast dance floor, past the pool tables, then through a sliding screen door if she is to find the charming outdoor patio. Smith courts the island’s blemished reputation; no doubt it’s good for business. Printed on the menu—next to a description of a tasty-sounding, Jamaican-style, steam-roasted red snapper with garlic, jalapeños, and thyme—is a vintage Red Wing Republican Eagle account of a notorious 1908 vigilante raid of Trenton’s seedier establishments. The Harbor regularly hosts bikini contests and sweaty, late-night dance parties, to boot. “It might be a restaurant, but it’s still the Harbor Meat Market,” laughed Smith. “You can’t have a fun place without being a little wild-ass rock ’n’ roll.”
Smith maintains this fast and loose atmosphere with the considerable assistance of his staff, some of whom travel each summer from Jamaica (where, incidentally, Smith keeps a winter home). The dozen or so guest workers, who began making the trek in 1999, have significantly boosted the quality, or at least the perceived quality, of the menu, especially when it comes to longstanding offerings like jerk rubs, “rasta pasta,” and even the breaded cheese curds. Furthermore, Smith explained that these hard-working employees spare him the burden of hiring flaky college students during the busy summer bar and restaurant season. Students, he said, tend to skip out when the weather turns nice.
In turn, the Harbor Bar’s waterfront views seem to ease the Jamaicans’ longing for home. On the patio, beyond the reach of the formidable interior sound system, toy toucans and tropical murals mimic a serene, unrushed Jamaican landscape. As Sandra, one of the Jamaican waitresses put it, “I take one look at this place and say ‘Let’s pretend we’re hanging out under a coconut tree and drinking a Red Stripe.’”
On one particular evening, a group of four Jamaicans—a cook and three servers—socialized at the tiki bar while the aforementioned dreadlocked bartender steadily poured caipirinhas, margaritas, and blue Hawaiians. Another ambled up and down the staircase leading to the seasonal workers’ living quarters, situated in an apartment just above the dance floor. A team of Jamaican and Wisconsinite waitresses worked a circuit of picnic tables, hammock swings, and plastic lounge chairs scattered along a tiny, shaded promontory. It felt like a cozy, family-owned resort, one that came together only after Smith accumulated enough cast-off patio furniture. Being there induced an inner calm that could only be broken by a trip to the restroom inside, where Jon Bon Jovi was blaring.
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