There’s history all over Houston, if you look hard enough. Or if you find the right pub crawl.

Best Bites Houston, a start-up walking tour service offering food- and beverage-centric walking tours, recently launched a tour focused on the cocktails and storied buildings of Downtown’s Historic District. For $69 per person, the Booze, Bites, and Historic Sites tour takes guests to four bars and restaurants from an always-rotating list of partners, each with its own historic significance. The experience—which founder and tour guide Star Gilani crafted with the help of historians like Minnette Boesel and Jim Parsons of Preservation Houston—highlights Market Square Park, the Main Street Aqueduct and several little-known remnants of Houston’s founding history, teaching guests about the city’s obscure Colonial and mid-century past.

Houstonia recently tagged along with Gilani on one of her latest Historic Sites tours.

Star Gilani takes folks on a tour through Downtown's history, with some booze along the way. Image: Carlos Brandon

The tour begins in the famed though under-appreciated Houston landmark, Market Square Park. Once a bustling 19th century commercial center, the square housed the first civic center and Houston’s first four city halls. After decades of neglect and use as a parking lot, the area was transformed in 2010 into an urban green space with a dog park and food vendors.

The booze and bites portion of the evening began properly at OKRA Charity Saloon. Since 2012, OKRA has donated nearly $1.3 million in proceeds to Houston-area charities. Many might not know the building’s history (founded in 1882 as the Casino Saloon) or that its gas-lit lanterns and wooden arches are original fixtures.

Guests were served the bar’s famous Green Tea Punch—a tart and refreshing concoction featuring Jameson, Peach Schnapps, and lemon juice—as well as a taster of Holler Brewing Co.’s classic German pilsner, Dollar Pills Y’all. Bites included homemade beef jerky from 44 Farms, a cauliflower plate from Coltivare, and fresh-baked chocolate chip cookies.

The next stop was a location with singular significance in both Texas and U.S. history: the iconic Rice Lofts Building. Opened in 1913 as the Rice Hotel, the original structure at 909 Texas was the site of the first Republic of Texas capitol building. Decades later, the hotel would gain notoriety as the place John F. Kennedy and First Lady Jacqueline Kennedy stayed a day before the president’s assassination in Dallas.

A smoked old fashioned at Lawless Spirits & Kitchen. Image: Carlos Brandon

On the building’s second level is Lawless Spirits and Kitchen, a speakeasy-style cocktail saloon showcasing a double-smoked old-fashioned. Guests were served smoked-brisket nachos and chipotle deviled egg and were offered a taste of the old fashioned and a lavender martini.

Next we stopped by Houston’s original infused tequila bar, El Big Bad, to try a pineapple and hibiscus margarita and one of the kitchen’s signature bites, plantain empanadas. The bar’s owners, known for creating hundreds of tequila infusions over the years, honored their 150-year-old building’s history by lacquering over and preserving smoke damage on its original walls.

The night ended on a sweet note with a visit to the Main Street Boomtown Coffee. The coffeehouse and bar transitioned from its former name, The Honeymoon Cafe, in 2019 but remains under the ownership of previous part-owners, Boomtown. The local roasters have kept coffee-based cocktails at the forefront of this beloved establishment in the heart of Main Street. We were served a piece of spiced coffee cake and a small glass of Brown Grasshopper, a milky signature cocktail featuring crème de menthe, crème de cacao, and cold brew.

A diverse bunch, the tour group of eight included out-of-towners, recent transplants, and suburbanites on a birthday weekend. Despite Houston’s lack of obvious tourism appeal, Best Bites helps shine a light on those oft-overlooked elements of our swampy boomtown’s rich history. The experience proves enlightening to both newcomers and locals alike—an important service towards preserving and appreciating the history and charm of Bayou City.