5 Reasons To Visit Bridgeport Before Fall

Mention Bridgeport as the scene for a prospective night out, and you might be met with a few blank stares and even some half-hearted objections: Isn't that on the South Side? Is there even anything to do there? But just because it's the historical home of both Mayor Daleys that doesn't mean that it's stuffy or—we know what you're thinking—lame.

Little by little, the quaint neighborhood has transformed into a hidden gem of stellar food, booze, sweets, and art—the perfect, tourist-free spot for a local staycay. So, have your transit card at the ready—here are our five must-hit to-dos for a progressive day in the self-styled "community of the future." Ready to explore?

Who says that Co-Prosperity Sphere and Zhou B have the corner on the art world in Bridgeport? If you find yourself in more of a buying mood, check out one of the neighborhood's artist in residence: Dolan Geiman. Working from his studio in the Chicago Sustainable Manufacturing Center (a green renovation that's pretty magnificent in its own right), Geiman dreams up mixed media masterpieces that usually focus on wildlife and Americana—with occasional homages to his Southern roots in the Shenandoah Valley. Viewings are available by appointment.

Dolan Geiman Studio, 1048 West 37th Street (between Morgan Street and Racine Avenue); 773-247-3775.

Top off the night by shuffling inside what looks like a low-profile liquor store. Closer inspection reveals a doorway behind the cash register that leads to the real Maria's, a backroom cocktail hangout that offers some of the best old-fashioneds and sazeracs in the city. Extra points for their creations like the "Bubbly Creek," a nod to the river that used to run through the old stockyards. And with Pleasant House bakery next door, this street corner is a gem.

Maria's Packaged Goods and Community Bar, 960 West 31st Street (at Morgan Street); 773-890-0588.

Organic paradise has arrived on earth. Not only does this healthy spot only use natural and pesticide-free ingredients, it also insists on serving up spreads from a sizable list of farms right here in the Midwest. Our favorite dish? The Nanadict: poached eggs, pupusas, chorizo, and a poblano cream that seals the deal.

Nana, 3267 South Halsted Street (at West 33rd Street); 312-929-2486.

Sometimes, you just gotta get off the pavement and into the field. Enter one of the city's best-kept secrets: 27 acres of rock-quarry-turned-park with wetlands, old stone walls, and open spaces beneath a spectacular skyline view. Basically the perfect marriage between the urban and the rural. Here's some free trivia: The location set one of the scenes in Boss, Kelsey Grammer's new Starz! drama about corruption in the Chicago mayor's office. Highlights include a fishing lake and an overgrown path snaking up the hill above the basin. Fair warning, though: no dogs.

Palmisano Park, 2700 South Halsted Street (between 27th and 31st streets).

Look no further than the funnel cake sundae at this walk-up ice cream parlor. Trust us — you can't find this one anywhere else in the city, and its fluffy, golden-brown dough smothered in ice cream reinvents summer dessert as we know it. Best part? It's only $3.75.

Sugar Shack, 630 West 26th Street (at Lowe Avenue); 312-225-6568.