Being a big city—any big city—in a state like Connecticut seems to be an uphill battle without end; you'll never be good enough, tidy enough, keeping-up-appearances enough to satisfy the unwritten requirements of a place that has always been uncommonly committed to beating back reality, even as it clawed at the front door.

This seems a rather difficult way to live, really, considering just how much of the state is (and for generations now, has been) still largely unrecovered post-industrial. It's like being at war with yourself. Like wishing half of your own person did not exist. This cannot be easy.

Some of Connecticut's urban centers get a partial pass—New Haven has Yale, it has some of America's best pizza. Stamford has all those glittering office towers. Hartford has the state government, and an increasingly great restaurant scene. Even humble (or is it humbled) New London has that properly nautical, New England vibe. Others are not so fortunate. The largest city in the state, Bridgeport, is among the least lucky.

Everybody passes through Bridgeport, everybody sees Bridgeport; how could you not, I-95 rips straight through the city's downtown. These days, relatively few people remember Bridgeport's outsized contributions to our shared heritage—P.T. Barnum lived here and was once the city's mayor, Bridgeport was an early center of automobile production, shortly before Henry Ford figured out how to do it cheaper and stole the show. The Frisbee was invented here. Subway, long before it became the world's largest fast food chain, was just Pete's Super Submarines on Main Street.

In modern times, Bridgeport has mostly been synonymous with struggle—its 1991 bankruptcy declaration, after years of decline, became national news. A downtown that long struggled to attract casual visitors, was hit by a particularly forceful tornado in 2010. And yet, there have always been bright spots. Great jerk chicken at spots like Rootsman Kitchen, terrific Turkish cooking at Bereket, and upscale Columbian at El Pueblito have always been reasons to stop by for a bite, perhaps followed by a visit to the Olmsted-designed Seaside Park, or the vintage-y Beardsley Zoo. Also, there has always been Black Rock.

Black Rock, down along the water in Bridgeport's far southwest, has for years been the anti-Bridgeport—sandwiched between affluent Fairfield and the worst of the city's post-industrial wastelands, Black Rock has long been one of those all-too-rare neighborhoods in Connecticut where economic diversity has been cause for celebration, rather than panic.

Black Rock has long been a place where food has served to bring the community together, from institutions like the Harborview Market, a bit of neighborhood history where people gather over breakfast and lunch, to the pioneering Bloodroot, a vegan-friendly café with an emphasis on local and seasonal that's been open for over forty years now. (It's also a feminist bookstore.) Long before ice cream became trendy again, Timothy's was one of the East Coast's better ice cream shops, and still is, a destination worthy spot on Black Rock's main drag, Fairfield Avenue, a strip that's home to a growing number of interesting restaurants.

Not that Downtown is going to be left out, not by a long shot—spots like Joseph's Steakhouse, opened in 2000 by a Peter Luger's veteran, or Ralph 'n' Rich's, an old-school Italian spot, opened at one of the lowest points in the city's history, have become destination spots for diners throughout the relatively affluent region.

These days, as in Black Rock, there's a new buzz around the city center, not to mention the rest of town; while grand plans to create a city-within-a-city at the downtown-adjacent Steel Point have yet to yield much more than a Bass Pro Shops location and a drive-through Starbucks, Bridgeport, apparently, isn't so much waiting around for the bolt of lightning, it's just getting on with it—that is, at least, within the restaurant community.

More than a handful of spots for noteworthy drinks and eats have recently been added to the mix, making the city a perfect day trip destination from nearby cities like New York or Boston. Headed to town? Here are just a few essentials.

Brewport

The largest brewery in the state (Two Roads) might be just a couple of miles away in Stratford, but this cavernous craft beer wonderland in Bridgeport's South End is having no trouble attracting attention—brewer Jeff Browning and his ambitious partners have created a destination-worthy spot featuring not only their own wide selection of beers, but also taps filled with other great local product, alongside a 10,000 lb. pizza oven churning out pretty good New Haven-style pies. brewportct.com

Nom-Eez

The image is all fun and the menu is definitely fusion-y, but this is still at heart a place committed to classic Vietnamese cooking, starting with the fact that you can start any day of the week the Vietnam way, with a steaming bowl of pho. Chef Matt Storch, at this point pretty much a celebrity in Fairfield County, buys hundreds of pounds of bones from noted craft butcher Fleisher's each week to make the broth. The casual spot shares space with an outlet of Donut Crazy, a strong new entry in a state where passion for that most American of breakfasts runs deep. nom-eez.com

Walrus + Carpenter

This accessible gastropub dedicated to the celebration of smoked meat has become a Black Rock institution in the few short years it's been around, a bold entry into Connecticut's surprisingly vibrant 'cue scene. A smoker out back yields great baby backs, pork shoulder and spares; for dessert, the Walrus Pie is the stuff of local legend: a chocolate chip cookie crust studded with smoky bacon pairs with creamy peanut butter ice cream, showered in candied bacon and chocolate. walruscarpenterct.com

Leisha's Bakeria

Very much a passion project for proprietor Leisha Young, this cheerful bakery and cafe brightens up any visit to Bridgeport's downtown. There's lunch, sure, but breakfast is where the real magic seems to happen—Morning Pies, topped with tomato, basil and mozzarella and a sunny side-up egg are a revelation; potato fans will flip for the hash brown waffle: freshly-grated red potatoes, peppers, onions, herbs and spices thrown into the iron and topped with grated cheese. Take that, Waffle House. leishasbakeria.com

Asylum Distillery