Early in my days of riding, I came across an article in one of my many motorcycle magazines on the “Best Places to Ride” in the United States. At the time, there was one route on the list that was unknown to me that immediately caught my attention above the rest, and I tucked it away for a future date.
Fast forward a few years, and I was looking for a dose of wind therapy to keep me going through the cold and dark winter months. On the spur of the moment, I booked a flight to San Antonio for a four-day weekend. The sole purpose of the trip was to spend a few days touring on a Harley-Davidson Road Glide I arranged through Caliente Harley-Davidson. For those that are unfamiliar, San Antonio is located in the middle of the very large state of Texas. For those who ride, it’s best known as the gateway to Texas Hill Country, an area that certainly has earned its place on that list for motorcycle destinations.
Less than an hour northwest of San Antonio, Hill Country largely consists of dry and rocky granite terrain that’s considered the dividing line between the southeast and southwest parts of the country. The area is rural, with a smattering of quaint towns with limited services and a unique mix of Spanish and German immigrant influences. It’s also the home of some pretty great roads and unique attractions.

Caliente Harley-Davidson was a short trip from the airport. The rental process was a breeze. After some paperwork and basic “orientation” with the bike, my partner and I were on the road. We traveled in our riding clothes, brought only a saddlebag liner as a carry-on, and had our own helmets. At the time we were still kicking it old-school, so we had prepared turn-by-turn directions on a magnetic map case attached to the tank of the bike. If I had been a better planner at the time, prepping GPS in the navigation system on the bike would have been a wise decision!
About an hour’s ride to the north of San Antonio is the beautiful town of Fredericksburg. Founded in the late 1800s, many of the original buildings remain standing along Main Street, giving it an “Old West” vibe. The German heritage of the area is on full display in the local restaurants and shops. There’s an eclectic mix of local attractions along with the seemingly out-of-place National Museum of the Pacific War situated right in the middle of town (guess that’s what happens when you’re the birthplace of Chester W. Nimitz, arguably the most famous WWII Pacific Fleet Admiral).

Fredericksburg is also central to many countryside attractions, connected by a network of winding rural roads that traverse the granite hills. Most well known is Enchanted Rock State Natural Area, a massive granite dome that seems to suddenly appear out of nowhere. While it’s only a 20-minute ride north of Fredericksburg, I used it as a stop in the longer “afternoon loop” of roads to the north and east of town. Placed towards the end of the ride, we used the climb to the summit as an excuse to stretch our legs. The view is pretty spectacular.
The next day, we explored more in the area, starting with one of the most peculiar tourist stops in Texas—a miniature replica of the English prehistoric monument, Stonehenge. The kitsch display comes with a few Easter Island Moai replicas tossed in for good measure. At about 60% of the size of the original English Stonehenge, this weird but wonderful roadside attraction was built in the late 1980s by two locals who clearly had more money than sense!
Our final stop in the Fredericksburg area was Luckenbach, which seemed almost like a ghost town. Like Fredericksburg, it dates back to the mid-1800s. For no particular reason, it never grew much beyond a handful of residents, with a peak population of less than 500 around the Great Depression. Since then, the population has plummeted, though its popularity as a tourist destination has seen a small “revival” after the town was privately purchased and a number of the local buildings were renovated to host music festivals and concerts.
Presently, the main attraction of the town is the combination of the General Store–Saloon–Post Office, which is located in one of the area’s original buildings that goes back nearly 175 years. Moreover, it’s a great spot to grab some food and a drink, as it’s only a 20-minute ride outside of Fredericksburg.
While we enjoyed cruising in the Fredericksburg area, the starring attractions of Hill Country are the famous Three Sisters. This is a connected series of county roads (Ranch-to-Market Roads 335, 336, and 337) that form a roughly 125-mile loop to the west of San Antonio. From the city, it’s about an hour ride to the town of Bandera and the OST Restaurant, which is worth a pitstop to fuel up with “Good ’ole” American fare in a cowboy-themed setting.
From there it’s only a stone’s throw to the start of the Three Sisters in Medina. Picking up the RM 337 heading due west out of town, you’ll immediately realize why these Three Sisters have earned their reputation as a biker destination due to their twisting bends and light traffic.
There are few roadside services along the route; they’re mostly concentrated in the biker-friendly town of Leakey, which is about a 45-minute ride west of Medina. While the loop might only take three to four hours to complete, many make Leakey the center of a multi-day exploration of The Sisters. That’s where you’ll find Trio Canyon Motorcycle shop, a combination store and restaurant that’s well worth visiting for some refreshments.
After exploring Hill Country for the better part of three days on two wheels, we had to return our rental Road Glide. Before flying home, we had the opportunity to explore San Antonio for an afternoon and evening, which was hardly enough time to satisfy our curiosity.
The Alamo is legendary, and so it was the first place we visited. But beyond the walls of the most famous landmark, there are many corners of San Antonio that deserve further exploring. Foremost is the San Antonio Missions National Historic Park. Here, you’ll find four of the five original Spanish Catholic Mission Churches preserved (Fun Fact: The Alamo, otherwise known as Mission Valero, is the fifth!).

No trip to San Antonio would be complete without a wander along the Riverwalk, an oasis of quiet that follows the rivers flowing through the center of the bustling city. The many great cafes and restaurants on the riverside pathway offer refreshments and a place to rest after long days on the saddle.

While this was my first trip to Hill Country, it certainly will not be my last. I’ve passed through the area a few times on my coast-to-coast rides, and I’ll be lucky if I can do it again soon.
Marketplace Inventory