A smear of orange and yellow spreads across a gray-blue evening sky as the sun begins its slow descent over Round Top. Surveying the picture-perfect display over a small pond and his expansive yard, a local utters what’s become a familiar chorus around these parts.

“Yeah, Round Top is the new Jackson Hole.”

His declaration isn’t far off. But how did a quaint Texas town with an official population that averages between 93 and 99 become analogous to the celebrity-packed city in Wyoming?

Credit — or blame (if you’re a Round Top native) — the wildly popular Round Top Antiques Show, which draws hundreds of thousands from across the globe twice a year and is known in shopping circles as one of the top antique events around.

While generations of locals in usually sleepy Round Top have built their livelihoods around the shows, smart Texans have started snatching up property so quickly that million-dollar bidding wars are now common. What for decades was a road trip for charming old trinkets and darn-good pie is now a Texas luxury hub.

But when the crowds depart, the old German town gets back to its Lone Star State roots of rustic charm, classic attractions, and colorful characters, perfect for a weekend stay. New retail, sundry shops, restaurants, and a microbrewery make Round Top a year-long choice for those needing an escape from traffic, high-rises, and clamor.

Now, Round Top is welcoming visitors — and shoppers — for Christmas, New Year’s Eve, and lazy winter weekends. Round Top's Town Square will host “A Classic Round Top Christmas” from 11 am to 1 pm on Friday, December 23, where families can gather at the town square gazebo for photos with the Grinch and some favorite characters. But there's much more to do in this quaint Texas town during the holidays.

Lodging

Thanks to the swarms of antiques show visitors, Round Top has no shortage of lodging, including charming bed and breakfasts, boutique hotels, cabins and cottages, and even sporting clubs and ranches, such as the sprawling Big Easy Ranch. Coming soon is the Cotton Pearl Motel, set to open January 1, 2023, and accepting bookings now.

Much of the lodging here is a study in preservation and adaptive reuse, with many home to buildings dating back to the late 1800s and Round Top’s founding. The Round Top Inn is literally a piece of Texas history, its compound home to the only surviving building that harks back to Texas’ cigar-making days.

Euro-inspired and striking, the white, circular hot tub and square pool at The Frenchie have become Insta-famous, with hundreds posting pics while lounging in the water while sipping wine. Three individual houses, one dating back to the 1890s, make up the Round Top Motel, conveniently situated in downtown just across from Rummel Square.

Expect rustic-chic surroundings in many hotels, such as The Vintage Round Top, which marries modern sensibilities with classic vintage flair (its Boho cottage is internationally acclaimed and has landed on many best-of lists). It’s quite hard to miss the Red Antler Bungalows while entering the town, the modern complex of black bungalows (which hark to Scandinavian rustic design) accented by unmistakable, signature red-antlered mounts constantly spur a “what is that?” from travelers.

The luxe Hotel Lulu, from legendary Houston restaurateur Armando Palacios and his wife, Cinda, follows the Round Top trend of bungalows/casitas on a compound, with a central courtyard and pool. Nestled just outside the bustling Henkel Square, it has become a go-to for urbane visitors who stay for the scenic vistas (we fell in love with the neighboring barn characters, namely a donkey, bull, and some swift llamas), and Lulu’s, the red-hot restaurant helmed by executive chef Jose Monterrosa. The downstairs dining room, chiseled in central Texas rock, is worth a peek, and the picturesque ll Cuculo bar is a must-visit for pre or post-dinner cocktails. Hotel visitors can plan for family stays in the two-bedroom Grandiosa suite; Grande suites feature a king bed and a “napping” smaller bed, and couples will love the romantic Amanti suite, with its soaking tub and porch.

Shopping and Dining

In Round Top, shopping is a must, starting with Henkel Square Market (201 N. Live Oak), just seconds away from Hotel Lulu. The bustling square, with greens and a fountain, is a go-to center to find jewelry, clothing, and home decor. One could spend hours at Southern Beasts, where the clever Mary Lou Marks crafts whimsical animals out of vivid upholstery. We scooped up vintage headbands and bracelets and lusted over the vintage cowboy hats and gear and one-of-a-kind paintings.

Next door is the exotic Sapana (translated to “dream” in Nepali), where owner Jolie Helms curates and imports outerwear, vests, quilts, totes, and more from India and Nepal — all while empowering the impoverished crafters in those countries.

A quick jaunt leads to our favorite Round Top art store, Humble Donkey Studio, a crafty playground founded by John Lowery, a former Houston marketing CEO who has turned his passion for Texan and animal-themed art into a two-story mecca of charm. Lowery celebrates in-store sales of his large pieces (in demand across the country) with wine, cowbell ringing, and the declaration that “a donkey got its wings.”

Fashionistas should stop by Marla Hurley’s chic boutique ModernMarla, where serious shoppers can grab luxe-label shoes, accessories, clothes, and more. (Be sure to score a cheeky “Kiss My Fancy Texas A*s” T-shirt for a Lone Star look that’s totally extra.)

Near ModernMarla, The Ellis Motel offers a little rock star Round Top vibe. Owner Lee Ellis calls his bar/hangout a “lounge and emporium,” one replete with a buffalo head and motorcycles. True to his culinary roots, Ellis owns the next-door Round Top Smokehouse, which quickly sells out of brisket, ribs, sausage, and more smoked fare.

A quick stroll to Royers Pie Haven is rewarded with some of the best pie in the state (try the Texas Trash pie). More bites can be found at Mandito’s (“little Armandos”), the Palacios-owned Tex-Mex cantina, and the fast-casual Popi Burger, which sits in the original Round Top General Store building. Beers on the deck are a must at Round Top Brewing, which also offers live music and chef-driven bites.

Last-minute holiday gifts and just-for-me items can be found at year-round shopping destinations such as Round Top Ranch Antiques and Round Top Vintage Market. Grab trinkets at Second Market and Company, Mallory et Cie, or Schmidt Jewelry & Gifts.

Take a stroll in the charming town square, where holiday music is piped through nightly and holiday ornamentation decks the halls. For some added holiday vibes, pay a visit to the world's smallest Catholic church.

Ringing in the new year? Indulge at wineries such as Busted Oak Cellars, Blissful Folly Farms, and Blue Mule Winery to toast 2023.

Photo by Pär Bengtsson

Hotel Lulu offers a luxe and rustic chic stay.