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This story originally appeared in the January 2018 issue with the headline “Rooms With a Past.” 

Get ready. San Antonio is preparing a yearlong celebration for its three hundredth birthday this year. Whether you’re going for Tricentennial Commemorative Week, May 1 through 6, or want to celebrate in your own time in 2018, here are five memorable hotels—all but one housed in buildings more than a century old—with fascinating and sometimes scandalous histories.

In 1909, when the St. Anthony Hotel opened near the Alamo, it was the talk of the town—the city’s first luxury hotel, with automatic doors and electric lights. Many thought the wealthy cattlemen who funded all this fanciness, B. L. Naylor and A. H. Jones, were crazy for investing in an undertaking of this size, a hotel with a whopping 210 rooms. A headline in the San Antonio Light on November 22, 1908, before the opening, was more optimistic: “Magnificent Structure Monument to Courage of Two San Antonians.” The hotel, which in the thirties became the first in the U.S. with air-conditioning, welcomed decades of glamorous guests: newlyweds Lyndon and Lady Bird Johnson dined on the roof before going on their Mexican honeymoon, in 1934, and a tuxedo-clad John Wayne hosted nine hundred guests in the hotel’s opulent Anacacho Room before the world premiere of The Alamo, in 1960. It lost its step in later years, until a thirty-month renovation that ended in 2015 restored the hotel to its original glory—with nineteenth-century bronze figurines, marble floors, and chandeliers—and outfitted it with modern touches, like a rooftop pool offering sweeping views of the city. Rooms start at $250.

Left to right: The Hotel Emma’s Sternewirth Tavern; The Three Emmas cocktail at the Hotel Emma.Photographs by Jessica Attie

As part of its Día de los Muertos celebrations, the Hotel Emma, the grand anchor of the Pearl restaurant, residential, and retail development, sets up a vibrantly adorned altar to its namesake, Emma Koehler. A fearless woman ahead of her time, Koehler took over running the Pearl Brewing Company after her husband, Otto, was killed in 1914 in a scandal involving two roommates—both of whom were also named Emma. The German immigrant led the brewery through Prohibition and died ten years later, in 1943. When Silver Ventures bought the Pearl property, in 2002, preserving its past was the first priority—the Emma is housed in the original brewhouse, built in 1894. Celebrated New York interior design firm Roman and Williams was enlisted to weave the Pearl’s artifacts into a modern design that has been much celebrated since the Emma opened, in 2015; there are nods to the past around every well-appointed corner. Book a room in the original brewhouse tower, where walls are left bare to reveal the existing brick and plaster. Rooms start at $350.

On a quiet stretch of the River Walk is the Hotel Havana, a 27-room boutique hotel built in 1914 by a local grocer, Edward Franz Melcher, as a guest house for customers. He wanted to create a space reminiscent of the Caribbean. Austin-based hotelier Liz Lambert reopened the Mediterranean Revival–style hotel in 2010 after a ninety-day refresh that mostly involved reupholstering and rearranging existing pieces, keeping the spirit and sturdy architectural bones of the place intact. Many of the palm trees that Melcher planted are still standing in the courtyard. The underground, candlelit Havana Bar evokes a speakeasy and boasts an Old-World-meets-modern-cool aesthetic. Rooms start at $145.

Left to right: the spacious lobby of the Hotel Emma, which features a cozy fireplace; the courtyard at the Menger Hotel.Photographs by Jessica Attie

Just one hundred yards from the Alamo is the Menger Hotel, said to be the oldest continuously operating hotel west of the Mississippi. It opened in 1859 as a place for guests of German businessman William Menger and his wife, Mary, to stay when visiting their brewery. The cavernous, all-cherrywood Menger Bar is the treasure of the historic property. Built in 1887, it is a replica of London’s House of Lords pub; Theodore Roosevelt reportedly recruited some of his volunteer Rough Riders regiment here in 1898. The Victorian hotel’s visual highlight is the front lobby, with its stained-glass ceiling, marble-footed Corinthian columns, open staircase, and gilded architectural details. The Menger was deemed the most haunted hotel in Texas by Sisters Grimm Ghost Tours, which hosts a three-course dinner on Friday and Saturday nights that starts at the hotel and ends with a ghost walk through the city. One of the most frequently reported ghost sightings is of an 1870s chambermaid, Sallie White, who was shot by her jealous husband. The in-house Colonial Room Restaurant is known for its mango ice cream. Former president Bill Clinton is such a fan that he had gallons of it shipped to Washington, D.C., for both of his inaugurations. Rooms start at $165.

On the other side of the Alamo is the towering Emily Morgan Hotel, built in 1924 as the Medical Arts Building, a thirteen-story high-rise with a hospital and doctors’ offices. The Gothic Revival–style building became a hotel in 1984. The song “The Yellow Rose of Texas” is an homage to the hotel’s namesake, an allegedly striking beauty who was rumored to have kept General Santa Anna so occupied during a siesta that he was caught off guard by the Texian Army as it moved in on San Jacinto. A rustic thirty-foot-tall dark-stone fireplace and paintings of the Alamo adorn the lobby. Rooms start at $139.

The bar at the Menger Hotel.Photograph by Jessica Attie

What to Drink

Raise a glass to San Antonio’s three hundredth birthday with a cocktail inspired by each hotel’s storied past. To experience more of San Antonio’s vibrant bar scene, consider attending the seventh annual San Antonio Cocktail Conference, starting January 10, with five days of tastings and parties.

The Three Emmas at Hotel Emma
The hotel might have one official namesake, but there are three Emmas behind its story. The Sternewirth tavern honors their memories with a concoction of Pearl beer, rose cordial, amontillado, gin, grapefruit juice, and lemon juice.

The Yellow Rose at the Emily Morgan Hotel
Sidle up to the marble bar at Oro, the in-house restaurant, for the Yellow Rose. With tequila, Southern Comfort, and orange juice, the drink is named for the hotel’s namesake and Santa Anna’s rumored special friend.

Hemingway Daiquiri at the Hotel Havana
Embrace the Cuban theme with the Hemingway Daiquiri, served in the hotel’s light and airy turquoise restaurant, Ocho, as well as its dark and mysterious underground Havana Bar. The daiquiri is made with 9 Brugal Especial rum, lime, grapefruit, and Luxardo maraschino liquor.

Menger Margarita at the Menger Hotel
It’s said that a mint julep was Teddy Roosevelt’s drink of choice, but it’s the Menger Margarita—with tequila, triple sec, a house-made sour mix, and a splash of orange juice over ice—that keeps the regulars coming back.

The Emerick at the St. Anthony Hotel
Each cocktail served at St. Anthony’s Haunt bar is inspired by a hotel ghost story. The Emerick—named after a guest who supposedly murdered his companion before taking his own life—is concocted with Jacob’s Ghost White Whiskey, simple syrup, orange bitters, and Cortas Rose Water.