Bridgeport on a Sunday morning: a seating queue winds snugly around the corner of the organic eatery Nana, its outdoor café space buzzing both with young brunchers and the bees that dive-bomb them from the planters. There’s a sidewalk sale assembled on the stoops of Jackalope Coffee and Tea House, attracting a crush of folks who are perhaps too cool for you. Bridgeport Coffee is also looking pretty hip. The one dude absently staring into his mug might well be nursing the aftereffects of an evening spent at Maria’s Packaged Goods—the titular Community Bar directly across the street, which has only just announced an expansion. The vintage neon signs of the coin-operated laundromats that line 31st Street match the neon joggers who trek the neighborhood’s nature preserve. Below its summit, parents and children celebrate local Little League with painted trophies and a feathered mascot, anticipating Jackie Robinson West’s ticker-tape triumph. In your pedestrianism, a dozen bikes overtake you, and you almost blunder into two of them head-on.

The “community of the future” seen here actually qualifies as one of Chicago’s oldest neighborhoods. This nineteenth-century Irish enclave, once named Hardscrabble, shares roots with the canal-building squatters who founded McKinley Park, just to the west. Although many of Bridgeport’s red-brick blocks still stand intact,  and the Art Institute has even restored a few churches in the area, the neighborhood is layered with cultural accretions.  The Polish and Lithuanian cohorts, the newer Chinese and Latino communities, the Zhou B Art Center and St. Mary of Perpetual Help have combined almost as smoothly as the flavors in Filbert’s Old Time Root Beer, first bottled in Bridgeport in 1926.  Accessible by the Red Line, the 62 bus,  and—as we’ve learned—positively crisscrossed by cycling paths, everything from a monastery-housed bed and breakfast (Benedictine Bed and Breakfast) to a “Front for the Left in the Arts”  (Lumpen Magazine) has flowed in over the years. Look to the shelves of Let’s Boogie Records or the Monster Island Toy Store for the neighborhood in microcosm: a lightly curated place populated with well-loved odds and ends drawn from around Chicago and abroad.

Sugar Shack
There’s a foolproof way to end a good summer day in low-slung, sunny Bridgeport. Wait for nighttime, emerge from whatever cool, dark room you have been taking cover in, and make the trip to Sugar Shack. More often than not you’ll find yourself waiting in a long sidewalk line behind everyone else who had the same notions in mind—notions like soft-serve, waffle cones, malts, rainbow sprinkles, and fairground fare like funnel cake and frozen bananas. It’s all deliciously excessive, reminiscent of a fifties-era ice cream joint somewhere in corn-fed Middle America. “Shack” is a dubious name as far as eateries go, but that’s just a nod to the modesty of the operation: one bright room on a quiet street, with one window where money goes in and one where snacks come out. It’s cash-only and strictly seasonal. For seating, most patrons avail themselves of curbs, stairs, and stoops, sweating and chatting over the drone of dripping air-conditioners. Sit awhile and you’ll realize it’s a frontier of sorts; delegates from Armour Square, Bronzeville, and Chinatown have all crept here over the interstates and under the viaducts in search of late-night treats. You might spot some takeout bags from Ricobene’s up the street, indicating a dining combination that really hits the spot if you happen to have been without solid food for a period of weeks. Sugar Shack, 630 W. 26th St. Sunday-Thursday, noon-10pm; Friday-Saturday, noon-11pm. (312)225-6568. (Andrew Lovdahl)

Blue City Cycles
Having recently celebrated five-plus years of business with a badminton soiree at Promontory Point, the mechanics of Blue City are a welcome fixture among Bridgeport’s can-do small businesses. Drop in at their corner storefront and they will give you a nice hello. They will ask, “Does this bike sleep in the rain?” and you will feel like a bad parent, and blame your roommate. They will not make a big deal about the cats running around the shop, so neither will you. They will get to work in their shop—right behind the counter, so you can watch the sordid proceedings yourself. They will refer you to a refreshingly precise service menu that lets you decide, piece by piece, how closely your ride aspires to the mythical condition of “fixed.” That’s anything from a wholesome “tune-up” to an exciting, possibility-fraught “overhaul.” They will get you back in business—depend on it—whether it’s right away or overnight. (In the latter case, they might call you at work the next day for a cheery status update, as if they were running a bicycle daycare.) When everything’s good to go, they’ll scoop the cats off the register, ring you up, wish you a good one, and remind you to use your shifter more often. You will leave with your thirty-day labor warranty, your five percent cash discount, and your two wheels below you. You will get back to the important stuff in life, like hexing taxi drivers, and working on your farmer’s tan. And you will, thanks to Chicago’s moonscape streets, be looking forward to another visit soon. Blue City Cycles, 3201 S. Halsted St. Hours vary. (312)225-3780. (Andrew Lovdahl)

Homestyle Taste Chinese Restaurant
A rule of thumb for dining in Chinatown is to listen in on the ambient conversation. If you don’t hear much English, you’re probably right where your stomach wants you to be. Homestyle Taste is approximately ten blocks and a Dan Ryan Expressway south of Chinatown, but the rule still holds true. Tucked into Halsted’s main drag but conveniently flagged by the bright red canvas enclosure over the doorway, Homestyle boasts a gratifyingly thick menu with a dizzying number of options. The Chef’s Specials leaflet is positively crammed with his hand-written novelties and experiments. Cumin stir-fried lamb? With the bone? Lamb kidney? (We settled on the more sedate scallion accompaniment.) Semantic quibbles like translating mushrooms as “fungus” ought only to tempt your curiosity. Heartwarmingly nutritious cabbage and tofu soup on a cloudy day; rich sauces that take “savory” seriously and exhaust you with meaty tones; a spicy dish that has a Taiwanese national loudly snorting to her local friend is righteously (read: unexpectedly) fierce! These and other offerings from Homestyle Taste will prove that it lives up to the near and dear sensibilities that its name invokes. Homestyle Taste Chinese Restaurant, 3205 S. Halsted St. Sunday-Thursday, 11am-10pm; Friday-Saturday, 11am-10:30pm. (312)949-9328. (Stephen Urchick)

Mr. Spanky’s Farm Fresh Artisan Foods
There it was, in my mailbox—not frozen. I’d never had bacon that hadn’t come from a freezer case. It looked safe though, and this bacon had a reputation. Mr. Spanky’s used to be a South Side institution. Before the owner, John Schultz, left the bacon-making trade to follow his passion for catering, the company made—among other meat-lovers’ favorites—bacon, breakfast sausage, and Sicilian sausage. Though the Bridgeport butcher has closed his doors for good, you can still have the dry-cured bacon—an applewood-smoked classic and, for the all-organic folks, a nitrite free  variety—delivered directly to your door. I was initially skeptical; there’s something unsettling about having a mound of meat arrive alongside your letters and electricity bill. But the bacon fulfills Mr. Spanky’s promise of bringing “the party to your mouth.” When thrown into a frying pan, the bacon crisps quickly, and its smoky scent lingers in the air for considerably longer than your ordinary store-bought varieties, sating your bacon craving for days to come. Mr. Spanky’s Farm Fresh Artisan Foods. Available online. (Alexandra Garfinkle)

33rd Street
For a place that’s only a couple miles from downtown, Bridgeport sure plays hard-to-get-to—there’s only one L station in the neighborhood proper and two more on the outskirts. That leaves a lot of people bumming around the bus stops on Halsted and 35th, a pair of supremely unreliable routes. It’s not all bad—it’s surely one of the reasons for the area’s low, low, tell-your-friends rents. But a daily winter slog to the Sox station is more than enough to sow the seeds of car ownership in even the staunchest young idealist. Biking is effective if you’re not going far; the short, skinny, angled streets conspire to keep local auto traffic slow and docile, and neat secret routes like the Loomis bridge to Pilsen help you venture a little further out. The problem with longer-distance forays is that Chicago has backhandedly blessed Bridgeport with an abundance of interstate highways. Take the Dan Ryan, a concrete canyon spanned only every now and then by a bridge choked with meat-grinding traffic. Bike lanes have a habit of quietly disappearing as you approach, which is the Department of Transportation’s way of saying “Good luck, kid.” But fear not—someone built a bridge extending tranquil 33rd Street. This creates a straight shot from Halsted (around Nana’s and Taqueria San Jose) to Bronzeville’s King Drive. Sights along the way include pretty Armour Square, Mies van der Rohe’s retro-futuristic IIT campus, and plenty of connections to north-south arteries. You can make short work of this trip even when the Sox are playing at home. If you prefer to cross further south, Canaryville’s Root Street (between 41st and 42nd) is another fine option. (Andrew Lovdahl)

Filbert’s Old Time Root Beer
About the size of a middle-school classroom, the area where Filbert bottles soda makes up a little less than half of his plant on the first floor of a brick building at 3430 South Ashland Avenue, in the McKinley Park neighborhood. It’s this small space, however, that helps make Filbert’s soda something special. See feature-length story. Filbert’s Old Time Draft Root Beer, 3430 S. Ashland Ave. Found throughout Chicago. (773)847-1520. (Robert Sorrell)

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