Even as strong earthquakes have shaken the region, the centuries-old city of Oaxaca remains largely unrattled. In the shadow of Monte Albán, the hilltop capital of the Zapotec civilization, this multicultural hub in the highlands of southern Mexico was once a quiet regional center. In recent years, the city has been transformed, for better or worse, as bohemian expats and artists have been drawn to its mild, semitropical climate, sturdy Spanish colonial architecture, rich culinary and craft traditions and thrilling art scene. Galleries and boutique hotels, upscale restaurants and trendy mezcalerias have opened in dizzying succession. Increasingly worldly, it remains a place where Mexico’s perilous and complex history reveals itself in ways both beautiful and brutal.
1) 4 p.m. GET CULTURED
Opened in 2011, the Centro Cultural San Pablo is housed in a former 16th-century Dominican convent and set around a tiled patio etched with bright green moss. The beautifully restored center has multiple exhibition and performance spaces, including one in the Rosary Chapel, and showcases everything from Oaxacan crafts — ornately carved alebrijes (whimsical wooden statues), indigenous textiles and traditional black pottery — to pop art, photography, string quartet performances and even the odd adults-only marionette show. The complex also has a cafe, an indoor children’s play area, a research library and a terrace restaurant popular with local bigwigs in natty business suits, which makes for excellent people watching.
2) 6 p.m. COMIDA LOCAL
A block east of San Pablo, in a storefront behind a pumpkin-colored facade, Cabuche is a festive restaurant serving reverential interpretations of street food and market staples: huaraches Menonita, edible tablets of sandal-shaped masa topped with tasajo (dried salted beef); Oaxacan string cheese and purslane (130 pesos, or about $7); and deeply flavorful soups, ranging from classic pozoles (choose between the red, green or white version, starting at 60 pesos) and a fiery shrimp caldo called levantamuertos (translation: raises the dead, 130 pesos). Sample the daily selection of guisados (25 pesos) — the miscellaneous stews that traditionally fill street tacos — like huitlacoche (corn fungus), potato with chile de agua (a light green pepper popular in the region) and rajas (strips of mild poblano pepper) with cheese. Specials, including house-made craft beer (dark and amber) and pulque (fermented sap from the maguey plant) flavored with celery, mango or oats, are advertised in multicolor chalk around the art-filled, two-room dining room.
3) 8 p.m. GRANDE DAME
Completed in 1909, one year before the Mexican Revolution, the grand Macedonio Alcalá Theater took six years to build. A baroque Renaissance-inspired facade topped by a green dome with an interior painted with portraits of artists and writers, the theater is among the most unusual buildings in Oaxaca’s Spanish Colonial city center. The striking structure hosts everything from operas and Latin American art house films to the Oaxacan symphony orchestra and book festivals. Drop by the ticket office to view the event calendar and request a tour of the century-old building.
4) 9:30 p.m. PIZZA PIT STOP
Eating pizza in a city revered for its regional Mexican food may seem like sacrilege. But the exceptional pies at two-year-old La Matatena are a worthwhile diversion. The mom-and-pop restaurant serves thin-crust pizza ranging from the traditional (pepperoni or margarita) to distinctly Mexican combinations like Oaxacan chorizo and roasted poblano chilies or chapulines (grasshoppers) and tomatoes. The 10-inch version (starting at 100 pesos) makes an excellent evening snack for two (vegan and gluten-free options are also available). Other offerings include Argentine-style empanadas (60 pesos) and mezcal from the mezcal distillery of the indigenous collective Pro Arte Ayuuk (125 pesos for a tasting of four one-ounce pours).
5) 10:30 p.m. SIP SMALL
Head to La Santísima Flor de Lúpulo (The Holiest Hop Flower), a nanobrewery that crafts potent, regionally inspired beers — still something of a novelty in Mexico — 50 gallons at a time on a four-tap rotation (90 pesos for a three-beer flight). The brewery’s kitchen, shared with the deli next door, makes a mean hamburger, and is also open until 1 a.m. for late-night hamburguesa cravings.
6) 9 a.m. FRESH BAKED
A stone courtyard set with multicolored Acapulco chairs and equipped with an excellent in-house bakery, Pan-Am serves croissants stuffed with spiced Oaxacan chocolate, cream cheese and blackberries, or ham and cheese (25 pesos) — and a full menu of brunch dishes, including a spectacular chilaquiles topped with organic eggs from “happy chickens” (85 pesos) and comforting molletes (house-made bread spread with refried beans and melted cheese and served with pico de gallo salsa, 72 pesos).
7) 11:30 a.m. GET CRAFTY
Stray from the pricey boutiques and souvenir shops lining the streets around Plaza Santo Domingo’s tourist district and seek out the graffitied workshop and showroom of Miku Meko Atelier, which sells traditional and contemporary textiles and doubles as a community space, offering classes in everything from backstrap weaving to button-making. Guibani Artesanal does one thing (and does it well): weaves colorful, artful housewares and furniture, including the Acapulco chair, from bright vinyl cording. For keepsakes that can fit in a suitcase, consider a lidded tortilla basket or a set of funky coasters. The sprawling new six-room popular art marketplace, Andares del Arte Popular, offers expertly made traditional crafts — everything from black ceramics to woven rebozos to pressed tin mirrors and ornaments — at responsible prices.
8) 3 p.m. FOUR-IN-ONE
Among Oaxaca’s new restaurants, Mesón Jalatlaco stands out. An airy covered patio with unfinished wooden floors and sleek Scandinavian-style dining tables and chairs, Mesón Jalatlaco is really two separate restaurants: Graciela, which specializes in seafood, and De Brasa Dura, which serves grilled meats ranging from a duck carnitas torta (180 pesos) to beef tongue in molé sauce (280 pesos). The coastal offerings include subtle, flavorful ceviches in four styles, including a squid ink, chorizo and peanuts version, and another with tomatillo, cucumber, celery and serrano chilies. All styles come with your choice of seafood (fish, octopus, oyster, sea snail or shrimp) and in three sizes, starting at 80 pesos for a small. Mesón Jalatlaco is also home to a wine shop and the craft brewery Casa Cervecera Tierra Blanca, which has its own tasting room, for those who want to sample beers without dining in.
9) 4 p.m. JOIN THE UNION
With its crumbling earthen facade and cavelike interior — dark and cluttered with barrel upon barrel and shelf upon shelf of unbranded bottles of mezcal — the Unión de Palenqueros de Oaxaca is nothing like the slick mezcalerias that have multiplied in Oaxaca in recent years. Instead, this storefront bottle shop sells its mezcal in repurposed Coca-Cola bottles with peeling labels. But what the Unión de Palenqueros mezcal lacks in stylish packaging or a swanky tasting room, it makes up for in a range of varietals — from cuishe to tobalá to pechuga — with prices so low (starting at 50 pesos a bottle) it would be easy to dismiss their product as swill. It’s not.
10) 7 p.m. SOUL FOOD
A six-table cupcake of a restaurant, with pastel pink and mint-green geometric shapes painted on its tables and paper flags strung across its ceiling, Casa Taviche is a casual spot with an outrageously affordable 75-peso menu del dia (three-course set menu). Served from 1 p.m. to 10 p.m., the menu includes three handwritten options for each of the first two courses — entradas (starters) and platos fuertes (entrees) — along with the restaurant’s choice of dessert and agua fresca. The options change daily, but include sophisticated dishes like a spicy pale green chile de agua stuffed with shredded chicken. Afterward, head to Casa Estambul, the mod art space and restaurant with wild, brightly colored murals across its walls, and a glowing, bright pink bar for a cocktail (try the Estambul Old Fashioned, which uses mezcal in place of whiskey, 100 pesos) and a glimpse of Oaxaca’s youthful night life.
11) 11 a.m. WORLD CLASS OF ITS OWN
The chef behind the most celebrated restaurant in Mexico — Enrique Olvera of Mexico City’s Pujol, which is routinely listed among the best restaurants in the world — opened his first Oaxaca restaurant, Criollo, on an unassuming, out-of-the-way stretch of Avenida de la Independencia in 2016. The open-air dining area abuts an expansive cactus garden with an open comal (a wood-fired griddle) and chickens and rabbits roaming the grounds. While Criollo’s dinner service is among the city’s most extravagant, its weekend brunch is an a la carte affair with modest prices. These midday meals, while exceptionally well-crafted, veer more traditional than the cooking for which Mr. Olvera is best known. Think mole enchiladas with organic chicken, cream and cheese (99 pesos) or market-style quesadillas with herbed guacamole (92 pesos).
12) 12:30 p.m. YOUNG AT HEART
Head to the Museo del Ferrocarril Mexicano del Sur and Oaxaca Children’s Museum. These twin institutions (both free), based in a renovated train depot and historic freight train cars, feature exhibits devoted to Oaxacan history, street-art-style murals on the rusted metal walls of once-abandoned box cars, a children’s library and a sprawling children’s museum with arts and crafts, a demonstration farm and an impressive playground that includes an in-ground trampoline. On your way back to the centro, stop at Basílica de Nuestra Señora de la Soledad, where Sundays are bustling with families and children in their elaborate Sunday best. Jardín Sócrates, the tiled patio outside the 1690 cathedral, has a half dozen or so ice cream vendors selling dozens of exotic flavors, from rose petal to tequila to star fruit for 30 pesos.
If You Go
The boutique hotel of one of Oaxaca’s most celebrated restaurants, seven-room Hotel Casa Oaxaca (García Vigil 407; 52-951-514-4173; casaoaxaca.com.mx) is surprisingly tranquil for its location in the city’s busy center. The backyard is planted with bougainvillea and cactus, with a swimming pool and a temescal, or sweathouse, which is available to non-guests for an hourly fee. Rooms start at $167. No children under 12.
The second location of the El Diablo y la Sandia (Boca del Monte, corner of Tinoco and Palacios; 52-951-207-7096; eldiabloylasandia.com), which goes by Boca del Monte or Mouth of the Mountain, is an artful, yet family-friendly and affordable, bed-and-breakfast with single rooms starting at $80.