Day 1  

I’m almost to my hotel in Oak Cliff, the historic neighborhood southwest of downtown Dallas, when I come to an itinerary-altering realization: I have more than two dozen places on my “must-visit” list but an all-too-finite amount of time. Check-in can wait. I reroute myself to Bee Enchiladeria (202 West Davis, 214-941-1233), a casual counter-service spot with a made-to-order menu. As I enjoy pork carnitas enchiladas aswim in a chipotle crema, I survey my fellow diners. There’s a pack of well-maintained ladies of a certain age, a young Spanish-speaking family, and a trio of tattooed dudes in skinny jeans. Already, I can’t help but be charmed by Oak Cliff’s laid-back vibe and cross-cultural appeal.

The humble enclave, which started out as a 320-acre farm in the late 1800’s, grew to be an affluent residential area that was annexed by Dallas in 1903. By the sixties, though, Oak Cliff was succumbing to disrepair and disrepute. But over the past decade, a turnaround has taken hold as artists, musicians, and entrepreneurs have transformed the area’s buildings and Craftsman-style houses into indie boutiques, art galleries, and top-chef restaurants. Factor in a new film festival and a new music festival, and you can see why Oak Cliff is often described as Big D’s Brooklyn.    

The Belmont Hotel (901 Fort Worth Avenue, 866-870-8010) certainly has all the markings of a hipster hangout. Built in 1946, this former motor court is now a spartan escape with 68 rooms spread among several white stucco buildings that sit high atop a bluff with a stunning view of the Margaret Hunt Hill Bridge. In my room, I find a green pleather armchair, a handwritten welcome note, and paraben-free toiletries. I then dash over to the Bishop Arts District, Oak Cliff’s pedestrian-friendly, restaurant-dense shopping nucleus. I meet some friends for an aperitif at Eno’s (407 North Bishop Avenue, 214-943-9200), a cozy pizza tavern, before our reservation at Hattie’s (418 North Bishop Avenue, 214-942-7400), one of the area’s fine-dining pioneers. Since I’m the only nonlocal in our party, I’m given first dibs on the fried green tomatoes. Dessert, however, is devoid of such niceties as we descend on a banana-almond bread pudding. Maybe I don’t share as well as I thought.

Day 2  

Because I’m still adding recommendations to my sightseeing list, today is going to be a “shop, eat, repeat” marathon. The Belmont’s adjoining restaurant, Smoke (901 Fort Worth Avenue, 214-393-4141), is swarmed with brunch enthusiasts, so I decide to try my luck at Oddfellows (316 West Seventh, 214-944-5958). The wait is just as long, but I’m fascinated by the baristas using their $15,000 Marzocco Strada (the Aston Martin of espresso machines). As luck would have it, two old friends happen to walk in, and we’re soon catching up over Bloody Marys and brisket hash. I mention there’s a new pie place a few blocks away, and off we go to Emporium Pies (314 North Bishop Avenue, 469-206-6126) to sample a slice of the Drunken Nut, which is laced with bourbon-soaked Texas pecans. I mention another sugary specialty shop nearby, and they gamely say, “What are we waiting for?” We walk over to Dude, Sweet Chocolate (408 West Eighth, 214-943-5943), which is overflowing with handmade creations like Jim Beam–and–walnut fudge and pillowy Valrhona marshmallows plopped into cups of hot chocolate. 

My friends peel off in search of a necktie, and I wade into dangerous territory: a gift shop called We Are 1976 (313 North Bishop Avenue, 469-248-2457), which stocks vibrant screen-printed posters and obscure Japanese notebooks (my Kryptonite). Equally hazardous to my bank account is Neighborhood (411 North Bishop Avenue, 214-943-5650), where modern furniture is arranged in Pinterest-worthy vignettes. Later that evening, I feel just as at home at Boulevardier (408 North Bishop Avenue, 214-942-1828), a nouveau French bistro whose cassoulet of duck leg confit and pork belly is the perfect chilly-weather meal. I would linger, but I’ve found out that Mindy Smith, one of my favorite singer-songwriters, is playing at the Kessler Theater (1230 West Davis, 214-272-8346), a seventy-year-old art deco gem that was restored last year. I’m beginning to think that Oak Cliff has karmic powers.

Day 3  

The only person waiting at Smoke this morning is my waiter as I waver between the blueberry-and-ricotta pancakes and the house-smoked salmon on buttermilk-dill toast. Fine, I’ll have both before heading off to a few more stops: IndieGenius (409 North Zang Boulevard, 214-941-0075), a “micro-boutique marketplace” that peddles local artists’ wares; M’Antiques (424 West Davis, 214-941-4195), a purveyor of manly curiosities; and Lucky Dog Books (633 West Davis, 214-941-2665), which has two floors of used hardcovers and paperbacks. When I score a half-price copy of my book club’s next selection, I feel as if the Oak Cliff gods are smiling on me again. 

When I discover there’s a juice bar and house-made sausages at Bolsa Mercado (634 West Davis, 214-942-0451), just thirty paces away, I’m ready to change my zip code. I settle into one of the burlap-covered wingback chairs, my fresh Just Beet It juice in hand, and pull out my crumpled itinerary. I resign myself to the fact that I’ll have to save some of Oak Cliff’s most buzzed-about eateries, like Bolsa (614 West Davis, 214-943-1883) (the market’s sister restaurant), Driftwood (642 West Davis, 214-942-2530), Lucia (408 West Eighth, 214-948-4998), and Lockhart Smokehouse (400 West Davis, 214-944-5521), for my next visit. As I’m leaving, I’m drawn to a red, white, and green shack called Taqueria El Si Hay (601 West Davis, 214-941-4042). It’s doing a brisk business as construction workers and soccer moms pull in and order $1.50 tacos. The lengua taco is my favorite until I eat the bistek, which is then overshadowed by the barbacoa. I decide that this may be my best meal yet—at least until I come back and cross a few more places off my list.