Do You Remember the End of Prohibition? The Esquire Tavern Does

On December 5, 2017, The Esquire Tavern celebrated their 85th birthday AND the 85th anniversary of the END OF PROHIBITION! What a great night! Here’s my review of one of the best bars on the San Antonio Riverwalk.

Esquire Tavern craft cocktail Quiet Little Voices
Craft cocktails? You’ve come to the right place! Here is Esquire’s Quiet Little Voices: cognac, Jamaican rum, Italian vermouth, sherry, and chicory-pecan bitters. Photograph, Ann Fisher.

What? Don’t tell me you don’t remember the day booze became legal again in the United States?

Geez — what was Congress thinking, outlawing alcohol? Then the depression hit, and everyone needed a drink!

On December 5, 1933, Americans everywhere celebrated the end of Prohibition and the repeal of the 18th Amendment.
On December 5, 1933, Americans everywhere celebrated the end of Prohibition and the repeal of the 18th Amendment.

The day we came to our senses and repealed the 18th Amendment, drinkers everywhere rejoiced and took to the streets to raise a glass legally again.

That day was December 5, 1933, and that’s the day the Esquire Tavern in San Antonio opened its doors for business.

On December 5, 2017, I swung into the Esquire Tavern to help celebrate their 85th birthday AND the 85th anniversary of the END OF PROHIBITION! It’s several years since I visited San Antonio, but I remember this bar fondly — and they continue to make amazing drinks and great food.

Prohibition ends on December 5, 1933!
Prohibition ends on December 5, 1933!

Tying One on at The Esquire

The Esquire is the oldest watering hole in San Antonio, and it sports the longest wooden bar top in the state of Texas. The ambiance at the Esquire has a vintage quality in keeping with its 1933 beginning, including great jazz playing in the background. On some evenings, you’ll find live music and burlesque entertainment.

The long, long wooden bar at the Esquire Tavern in San Antonio.
The long, long wooden bar at the Esquire Tavern in San Antonio. Photograph, Ann Fisher.

Their cocktail menu boasts ten house-created drinks with catchy names like The Texecutioner, as well as all the classics we know well.

Boar's head decoration the Esquire Tavern in San Antonio
The boar gets festive for the holidays!

I felt a personal challenge here, and decided to visit the Esquire Tavern twice in one day to maximize the number of libations I could sample and write about for my blog . . . . without ending up lying in a flowerbed along the Riverwalk.

I know. Sigh. It’s a tough job, but I just had to put on my big girl panties and get the job done.

Seriously though — my approach to writing about restaurants and bars when I travel alone is to go more than one time, if at all possible. I get to try more things, and I also have a chance to check on consistency in service and the quality of the food. Otherwise, I have to order a selection of dishes, knowing I’ll only be able to eat a little of each one. Wasting food is not something I like to do.

Esquire Tavern's Wonderlust King cocktail
The Wonderlust King. Yes, I know it looks the same as Quiet Little Voices, but it’s not. And it’s my fave! Photo, Ann Fisher.

I started with Quiet Little Voices (cognac, Jamaican rum, Italian vermouth, sherry, and chicory-pecan bitters — see top image) and went on to the Wonderlust King (rye whiskey, Amaro Nardini, Italian vermouth, Xocolatl bitters, and orange bitters).

These are both inventive variations on the Manhattan, and it was fascinating to see a drink with no rye whiskey, Quiet Little Voices, made to emulate the flavor you’d expect from a Manhattan. Both cocktails were outstanding, but my fave was the Wonderlust King: the Xocolatl Mole Bitters, with its combination cacao, cinnamon, and spice, along with a touch of Amaro Nardini, citrusy with a hint of licorice — makes this drink really special, and different.

Food at the Esquire is creative, but unpretentious — so right for one of the oldest bars in Texas. The chef focuses on making everything in-house, with organic, locally sourced ingredients, and the resulting quality of the food is outstanding. There’s a reason their bar program earned a James Beard nomination this year. You’ll find great bar nibbles, burgers, salads, and big plates. Find the current Esquire Tavern menu here. I took a look at all of this, and chose to focus on the small plate bar food.

Prices? Appetizers range from $6 to $12, Burgers, salads, and almost all mains run from $11 to $19. The most expensive item on the menu is the Texas Wagyu Beef Ribeye at $32. You’ll spend most of your tab on the craft cocktails at $10 to $14 apiece.

Chalupitas at the Esquire Tavern in San Antonio - one of the best bars on the Riverwalk
The Chalupitas were outstanding!
Riverwalk entrance to the Esquire Tavern in San Antonio
Riverwalk entrance to the Esquire.

My first choice out of the gate: The Esquire’s Chalupitas. Classic chalupas are a fried corn tortilla covered with a savory filling — and these little chalupas are wonderful. Organic chicken, chipotle refried beans, chimichurri, white cheddar, salsa verde, and a dollop of sour cream with fresh cilantro. Fresh, bright flavors — smokiness and a little heat from the chipotle pepper, without enough to be hot. I loved the unexpected combination of chimichurri, which has a bit of vinegar in it, with the salsa verde. It’s hard to write about them without wishing I could order them again — right now please!

Two drinks and one appetizer filled me up at lunch. I left the oldest bar in San Antonio, and headed to the Menger Hotel, the oldest hotel in Texas, to do some writing and to take a nap — and get ready for round two at the Esquire.

One of the Best Bars on San Antonio’s Riverwalk

If you find yourself in San Antonio, and you’re a visitor, then you will hit the River Walk.  Problem: many of the River Walk restaurants are either national chains or stale local restaurants slinging mediocre queso to capitalize on the tourist traffic. Do not despair! There are some wonderful places to eat and drink in downtown San Antone, and the Esquire Tavern is a fine place to start.

The Esquire Tavern has two entrances: one on the Riverwalk for the tourists, and one on Commerce Street, which more locals tend to use. I love the classic neon sign over the street side door. If you have difficulty with stairs, you’ll want to enter on the Commerce Street side.

I was lucky to be able to reserve the last available table this evening, since the Esquire was having a major party to celebrate its 85th birthday.

First Note cocktail at the Esquire Tavern in San Antonio - one of the best bars on the Riverwalk
The First Note — often I associate pink drinks with overly super-sweet — something I don’t care for, but First Note is nicely balanced.

My second foray into the Esquire’s cocktail menu started with their First Note, made of Aguardiente de Cana, Amaro Ramazzotti, guava, honey, lime. Enough citrus from the lime, along with some bitterness and spice from the Amaro to offset the sweetness of the guava and honey — resulting in a nicely balanced drink.

As part of the birthday party festivities, wait staff were passing hors d’oeuvres, one of which were the Esquire Deviled Eggs — which was great since I’d planned to order them. These free-range eggs were perfect, creamy concoctions topped with pink peppercorns and garnished with arugula.

So good!
The Texecutioner - one of the many craft cocktails at the Esquire Tavern on San Antonio's Riverwalk
The Texecutioner is aptly named. Too many of these, which are very, very easy to drink, and you’ll be sleeping under a bridge on the Riverwalk . . .

Second drink of the evening: The Texecutioner. With a name like that, I just had to try it. This is a combination of Espadin Mezcal, Xtabentún (a Mayan anise flavored liqueur), Cocchi Americano, and fresh grapefruit juice. Another great cocktail — very refreshing. I think it would be particularly nice on hot summer nights — something San Antonio has a lot of!

In addition to the deviled eggs, wait staff were passing chicken-fried oysters, which are NOT on the menu at the Esquire — but available in their second bar (Downstairs at the Esquire). The oysters were so good, that I have no pictures. Sorry 😦 .

About the same time, I ordered the Esquire’s Shrimp Toast, envisioning a couple of little bite-sized appetizers, you know, like you’d expect shrimp toast at a Chinese food restaurant to be.

Instead, I got shrimp TOAST. Texas-sized SHRIMP TOAST.

Wow! Crispy, fresh, perfectly fried — it’s like a Monte Cristo sandwich lost its ham and cheese, cavorted with fresh shrimp mousse, and ended up settling down in San Antonio. A crunchy bite of the toast, with a smear of chèvre, some chives, and a drizzle of jalapeño jelly syrup: this stuff is good. Wickedly good.

Shrimp Toast at the Esquire Tavern in San Antonio - one of the best bars on the Riverwalk
Shrimp Toast at the Esquire .Tavern is HUGE! And yes, I returned to my favorite drink, the Wonderlust. Photograph, Ann Fisher

Well, the Shrimp Toast finished me! But the next time I’m back in San Antone, I’ll head back to the Esquire and give you an update on other dishes here. I finished up my evening here, and headed back towards the Menger and a good night’s sleep — pausing to catch the square in front of the Alamo all dolled up for the holidays.

Merry Christmas from Texas!

Alamo and a Christmas Tree
As a sixth generation Texan, the Alamo is mighty important to me — lovely to see the mission at Christmas. Photograph, Ann Fisher.


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