San Antonio to Loving on Texas Highway 16

Huge apple pies, a Japanese submarine, handmade soaps—and a dressed flea.

TEXAS HIGHWAY 16 IS AN ODDS-AND-ends highway, seemingly cobbled together from bits and pieces of preexisting roads. I’d be tempted to call most of it a two-lane blacktop except that the color has faded to gray. It starts on the west side of San Antonio, cuts a swath through the Hill Country, then steers a semi-straight path northward through the west central part of the state to end some forty miles south of Oklahoma. The country it bisects, especially the northern half, is pure Texas: hilly and hardscrabble, full of limestone and red rock, prickly pear, yucca, and juniper. If, like me, you enjoy solitude with just a little company now and then, this is your road.

I headed west out of San Antonio on a blustery day, eager to reach the Hill Country with its soothing purple vistas and lambkin-like clouds. My first stop was Bandera, the self-styled Cowboy Capital of the World. No visit here is complete without a stroll around the sprawling Frontier Times Museum, a mesmerizing if spooky repository of Western memorabilia, yellowing Life magazines, a forties permanent-wave machine, and a dressed flea. For total cowboy immersion, stay at one of the dude ranches like the Mayan. Or try the more citified Mansion in Bandera, a bed-and-breakfast in a nineteenth-century limestone house (tip: The remodeled rooms are best). The top breakfasts and lunches in town are at the Fool Moon Café (eggs Benedict, pan-seared salmon). But the most fun is Mac and Ernie’s Roadside Eatery, a really bare-bones spot in Tarpley, twelve miles west of Bandera. Here talented chef Naylene Dillingham-Stolzer cooks in an open-air kitchen, frying up catfish and grilling pork tenderloin, the latter of which comes with a sweet-tart Vietnamese dipping sauce.

To me, the prettiest part of Highway 16 is the shady stretch between Bandera and Medina, where the road dwindles down to two narrow lanes next to the Medina River. The hamlet of Medina itself has become the unofficial apple capital of Texas (have you noticed that every Texas town is the capital of something?). The Love Creek Orchards cider mill and store is apple-doodad headquarters and also sells fresh local apples in season, from late July into October. You can get a light lunch here or at Keese’s Bar-B-Que down the street, and if you’re in town at night, try Love Creek’s “grill thrill” on Thursday or Keese’s steak night on Saturday. A trip to Medina also demands the purchase of a whole apple pie, from either Love Creek or Tootie Pie!, where pie queen Ruby Lorraine “Tootie” Feagan makes fabulous five-pounders. As I left town at dusk with one of Tootie’s monsters riding shotgun, I was treated to a Sistine Chapel-quality sunset of creamy clouds shot through with pink and gold. I wouldn’t have been surprised if cherubim and seraphim had come bursting out of them like cheerleaders at halftime.

Within living memory, Kerrville was a distinctly Western city; now the poor dear is franchised to death. I found a few shreds of local character in Old Town, a moderately interesting shopping, arts, and dining district centered on the intersection of Earl Garrett and Water streets. Here I also peeked into the Hill Country Museum, located in a fine Romanesque edifice that famed architect Alfred Giles designed as a home for rancher and banker Charles A. Schreiner. The best eating I discovered was the Southern-style cooking, including steaks and fresh seafood, at Joe’s Jefferson Street Cafe, in a two-story Victorian house. The next morning I got a latte for the road at Cappuccino’s (in your car, no one can see you scarfing down a pound of pie all by yourself). By the way, for lodging, try the appropriately Western Y.O. Ranch Resort Hotel. There are also chain motels galore on Texas Highways 27 and 16.

If Kerrville is—or was—cowboy to its core, Fredericksburg is genetically German. Of course, these days the tidy nineteenth-century stores cater less to locals than to marauding herds of visiting boomers. Even so, I love Fred, so let me tell you my favorite places. I like to have breakfast or lunch at Rather Sweet Bakery (good cappuccino, great nutmeg muffins). I also do lunch at the Peach Tree (creative soups, sandwiches, and quiche, cottage setting), and I would have to be abducted by aliens before I would miss dinner at the Hill Top Café, the most soul- and gimcrack-filled place in the area. For lodging, I like the log-cabin- mit-Jacuzzi at the Chuckwagon Inn.

When I’m frivolous and flush, I prowl the Homestead’s two shabby-chic home-furnishings and accessories stores. On this visit, though, I felt serious, so I stopped at the small, excellent Admiral Nimitz Historic Site, a collection of World War II memorabilia including a creepy two-man Japanese submarine.

At Harry’s on the Loop, north of Fredericksburg, I stocked up on excellent mesquite-smoked brisket and listened to regulars around the potbellied stove discuss the fate of a giant possum somebody had trapped the night before. Luckily, I saw no possums, giant or otherwise, on the Willow City Loop, one of the prettiest drives in the Hill Country. (From Fredericksburg, head northeast on Highway 16 for 14 miles, turn east on FM 1323, and go 2.7 miles to Willow City. Harry’s is to


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