A Transformative Weekend Getaway in Historic Laredo

Directions to Laredo are easy. Get on Interstate 35 and head south. Go far enough and you’ll get there eventually. Coming from the Valley? Take a left at the Whataburger in Falfurrias and keep going. The flat scrub of South Texas leads to this sprawling border town spread across a jagged crook in the Rio Grande. Today, 250,000 people live in the city that was originally founded as a Spanish colony in 1775. Laredo has long been a nexus where Mexico and Texas commingle. Its most popular and enduring cultural festival, the monthlong George Washington’s Birthday Celebration held every February, features a jalapeño festival and a debutante ball in full U.S. colonial garb.

Laredo is now experiencing a renaissance. Local entrepreneurs, chefs, and artists are transforming the city into much more than a historic gateway into Mexico. Next time you sing the folk song “The Streets of Laredo,” just know they’re busier than ever.

1 / The Laredo Mansion
Local businessman Peter Leyendecker built this mansion in the early 1900s. It was refurbished and turned into a boutique bed-and-breakfast in 2019. The transformation was part of a downtown revival of historically significant structures. Choose one of four suites, each themed to reflect different aspects of Laredo culture. Suites range from
$79-$200/night.

2 / Laredo Kayak
Check out the diverse bird population of Laredo while you kayak down the Rio Grande with Rick Rodriguez, a river recreation revivalist and owner of Laredo Kayak. For $65, Rodriguez provides the kayak, paddles, life jacket, and guidance down a 4-mile stretch of the river. Families, beginners, and seasoned paddlers are welcome on the mostly serene route.

3 / Laredo Center for the Arts
Located in the original 1880s city hall building, the Laredo Center for the Arts showcases local artists and hosts musicals, festivals, and kid-friendly art classes run by working artists in a variety of media. Join other art lovers on the first Friday of each month for Caminarte, an art walk through downtown that starts at the center and explores historic buildings.

5 / Avenida San Bernardo
Once the highway to San Antonio, San Bernardo Avenue has attracted tourists to shops along the 40-block corridor for decades. The shops are full of Mexican imports, such as clay pottery, furniture carved by hand, silk rebozos, and more, all sourced directly from artisans. There are also restaurants and nightlife in the area.

6 / Casa Ortiz​
This nearly 200-year-old hacienda located downtown is at the center of the city’s first Friday art walk, Caminarte. Built by cattle rancher Don José Reyes Ortíz around 1830, the roughly 12,000-square-foot property is now owned by Webb County. The nonprofit Laredo Cultural District hosts cooking workshops, movie screenings, live music, and dance performances on-site.

7 / Iturbide Street
Known locally as “It Street,” the strip is home to more than a dozen bars and clubs in the center of Laredo’s historic downtown, making it the heart of the city’s entertainment district. The street is closed to traffic on Fridays and Saturdays, keeping it pedestrian-friendly for bar hopping. View the restored storefronts and try out local grub from food trucks.

Jam Session

Jamboozie, Laredo’s most popular music festival, has brought people downtown for music, food, and fun for over 20 years. Originally a Mardi Gras wannabe, this March festival has shed its imitator skin and become a daylong, music-centric showcase featuring local talent and big-time headliners across multiple stages and genres on a closed city block downtown.­ ­laredomainstreet.org/jamboozie