During the U.S. Prohibition era, heavyweight boxing celebrity Jack Dempsey built a massive resort on the Ensenada  waterfront called the Playa Ensenada Hotel and Casino.
On opening night in 1929, Bing Crosby and the Xavier Cugat Orchestra entertained the crowd. A local singer named Margarita Carmen Cansino joined the orchestra—and later changed her name to Rita Hayworth.
A symbol of Ensenada’s newfound prosperity, the resort thrived for a few years until the repeal of Prohibition and the onset of the Great Depression sent most of the gamblers home. Management tried reopening the hotel as the Riviera del Pacífico, but by 1938, the doors had closed for good.
Forty years later, the Mexican government intervened and restored the legendary building as the city’s Centro Social Cívico y Cultural Riviera (Social, Civic, and Cultural Center, corner of Costero and Riviera, tel. 646/176-4310). It contains government offices and a public library as well as a small museum, the Museo de Historia de Ensenada (tel. 646/177-0594, 9:30 A.M.–2 P.M. and 3–5 P.M. Mon.–Sat., 10 A.M.–5 P.M. Sun., by donation), with historical exhibits that represent the indigenous people of Baja California, the era of European exploration, and the Dominican missions.
The Galería de la Cuidad (tel. 646/177-3130, 9 A.M.–6 P.M. Mon.–Fri.), at the north end of the building, showcases the works of Baja California artists.
Throughout the building, much of the original tile and paintings have been preserved. The street-level Bar Andaluz features a mural by Alfredo Ramos Martínez (1871–1946), who established Mexico City’s Las Escuelas de Pintura al Aire Libre (Schools of Painting in the Open Air).
Ensenada’s Museum of Regional History (Gastelum near López Mateos, tel. 646/178-2531, 10 A.M.–5 P.M. Tues.–Sun., by donation) occupies a former 1886 military garrison that housed the Ensenada jail until 1986. The permanent collection consists of native artifacts.
This historic building downtown was built by the U.S.-based International Land Company of Mexico, which acquired much of the coastline from the Mexican government in the 19th century. Mexico’s Aduana Marítima (Maritime Customs) took over in 1922. Then the Instituto Nacional de Antropología e Historia (INAH) stepped in to restore the building and convert it into a museum (Ryerson and Calle Uribe, tel. 646/178-2531, 9 A.M.–4 P.M. Tues.–Sun., by donation). Temporary exhibits cover various Mexican cultural themes.
Ensenada’s malecón, built in the 1990s, is a relatively new fixture on the waterfront. With its giant Mexican flag and bay views, the promenade is a good place to get your bearings before a walk around town. At the north end of the malecón are the sportfishing terminal and mercado de mariscos (seafood market).
Near here, Plaza Cívica features statues of three pivotal figures in Mexican history: Benito Juárez (Mexico’s first president), Padre Miguel Hidalgo (initiator of the Mexican Revolution), and Venustiano Carranza (first president after the revolution). At the south end, across the narrow Bahía Ensenada, is the cruise ship pier and the Riviera del Pacífico.
Ensenada  has a long history in the grape-growing/winemaking business and a growing reputation for bottling world-class vintages. Most of the vineyards are located in the nearby Valle de Guadalupe, but several operations have offices and/or tasting rooms in downtown Ensenada.
Part of Bodegas de Santo Tomás (Miramar 666, tel. 646/178-3333, www.santo  tomas.com, 10 A.M.–9 P.M. Mon.–Sat., 10 A.M.–6 P.M. Sun.), Tienda Miramar is a good place to get acquainted with the local varietals. As Mexico’s oldest winery, its roots go back to the Dominican mission in the Valle de Santo Tomás. The winery offered its first wine to the public in 1888 and moved its winemaking headquarters to Ensenada in 1934. Today most of the action centers around its vineyard in the Valle de Santo Tomás. The winery also runs a restaurant, shop, and tours at Km. 95 on Mexico 3 in the valley of San Antonio de las Minas.