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Take a 5-Day Road Trip Through Texas Hill Country

You'll enjoy wine, charming small towns and urban fun on this route from Austin to San Antonio

a map of a texas roadtrip next to a field of texas hill country bluebonnets

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This scenic road trip takes you through Central Texas’ acclaimed Hill Country, a fantastic region for wines. Beginning in music-centric Austin and ending in San Antonio, the tour leads you on a slow, hilly ramble through small towns with rejuvenated Main streets and past vineyards, farms, peach and apple orchards, and lavender fields.

sunset over lady bird lake in the city of austin texas

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Day 1: Austin

Bustling Austin, the state capital, revels in its slightly eccentric, music-obsessed reputation. Spend your day and evening in South Austin, an attraction-filled area just south of downtown that some consider a microcosm of the city’s spirit. 

A few options for the day: Take a stroll or ride along the 10-mile Ann and Roy Butler Hike-and-Bike Trail at Lady Bird Lake. (You can rent a set of wheels at Barton Springs Bike Rental & Tours.) Afterward, if you've packed a swimsuit, take a dip in nearby Barton Springs, a quarter-mile-long swimming hole beloved by locals with a temperature between 68 and 70 degrees.

Also consider exploring SoCo (South Congress), an eclectic entertainment district about 2 miles east of Barton Springs. There, eccentric shops sell everything from funky artifacts to handmade cowboy boots, and you'll find lots of spots for tacos and other quick bites. Grab a hot one at Jo’s Coffee.

For hearty meals, there are many great restaurants in the SoCo area. For lunch or dinner, try Loro Austin, a local hot spot near SoCo where two James Beard Award winners fuse barbecue and Asian cuisines with tasty results. On a nice night, grab an al fresco table at Perla’s in the heart of the district for fun people-watching and a delicious seafood meal. The wood-grilled Creole oysters are as good as the name sounds. 

For your evening entertainment, take your seat in a SoCo mainstay: the Continental Club, the legendary live-music venue that hosts performances on its famous stage daily.

Or have a cocktail in the Rainey Street entertainment district, an enclave of 19th-century bungalow houses turned clever bars on the southern edge of downtown, less than 2 miles from SoCo’s main buzz. Try Icenhauer’s, housed in a well-preserved circa-1895 home.

Where to stay: A former union hall near Barton Springs, the 93-room Carpenter Hotel appeals with a minimalistic, mid-century chic feel.


the old hye post office and store west of johnson city texas

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Hye Market

Day 2: Austin to Johnson City/Hye (92 miles)

Prepare for a day of wine tasting with a hearty breakfast at Forthright, a cozy café in downtown Austin. A favorite: the thickly cut avocado toast.

Depart Austin on Highway 290 West, then watch the Hill Country terrain appear almost instantly as you make your way about 40 miles down the road to Dripping Springs. There, in a revamped historic district, you’ll find breweries, distilleries, shops and even a wedding venue. Get a boost with a hot house-roasted brew at Mazama Coffee Co. & Roastery. 

Hop back on 290 (and Ranch Road 3232) for 19 miles, taking a short detour to Pedernales Falls State Park. At this leafy haven, stretch your legs on the half-mile Twin Falls Nature Trail, where two waterfalls cascade down about 30 feet into a natural spring pool.

Continue about 23 miles on 290 to the tiny town of Hye (population 238), favored by oenophiles and spitting distance from the birthplace of President Lyndon Baines Johnson. Grab a pecan salad or BLT sandwich at the Hye Market, adjacent to the Hye Post Office, where LBJ purportedly mailed his first letter at age 4.

Just a short drive away is Ron Yates Wines, located right off the highway. Drop in and enjoy a glass of cabernet sauvignon or tempranillo on the patio, surrounded by verdant grounds. Another option for wine lovers: Drive 10 more miles along 290 to Johnson City, where you can tipple in a treehouse at Sandy Roads Vineyard while you learn about unusual grapes, such as mencia and prieto picudo. If you’re hungry, munch on luscious cheese and charcuterie.

Where to stay: The Carter Creek Winery Resort & Spa sits between Johnson City and Hye. Besides 78 ranch house-style villas, the property boasts its own tasting room, a brewery/restaurant and a spa.


Becker Vineyards oak aging barrels at Texas Hill Country

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Becker Vineyards

Day 3: Hye/Johnson City to Fredericksburg (30-plus miles)

Today, savor more wine en route to the Hill Country’s most emblematic town, Fredericksburg, founded by 19th-century German settlers. As most wineries lie in the countryside, you’ll be backpedaling to the main road after stops.

Among the best is family-owned Pedernales Cellar. From Carter Creek, travel west on 290 for 11 miles, then 2 miles south on Ranch Road 1623 to reach the pastoral estate. Here, you can sample ethereal viognier and heady tempranillo wines while taking in striking views. 

If you continue west for about 7 miles on 290, you’ll hit Becker Vineyards, the unofficial regal prince of this wine region. In a replica 19th-century stone barn, you can sip wines so exceptional that they’ve been served at the White House. 

Three more scenic miles down 290 takes you to the Texas Wine Collective, serving wines from three local wineries: Brennan Vineyards, Lost Oak Winery and McPherson Cellars.

Drive along 290 for another 10 miles to reach Fredericksburg, a lively town where German restaurants, festivals and shops share space with vestiges of the frontier (cabins and cows) and contemporary shops and galleries. Celebrate the town’s roots with Wiener schnitzel at the family-owned Old German Bakery & Restaurant.

Stroll and relax in town, check into your cabin or cottage at Cotton Gin Village, and later dine at Cotton Gin’s Cabernet Grill for a contemporary riff on Texas-style cuisine. Try the Texas Twinkies: jalapenos stuffed with beer sausage and cheese.  

Not ready for bed yet? Head to Lost Draw Cellars for live music and more spectacular wines.

Where to stay: At Cotton Gin Village, you can choose from 14 cabins and cottages teeming with old-time charm. Come morning, breakfast is delivered right to your door.


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shopping promenade in historic german settlement fredericksburg texas

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Historic Fredericksburg

Day 4: Fredericksburg to San Antonio (89 miles)

Linger in your cabin or cottage over breakfast in bed, then hit the road. Pecans, pumpkins, lavender, peaches, berries and apples all grow abundantly in the Hill Country, depending on the season. Many farms offer pick-your-own programs, an entertaining (and delicious) way to immerse in the terrain. A good choice on 290: Jenschke Orchards, a storybook family-run farm about 8 miles southeast of Fredericksburg that grows a variety of crops.

If you take U.S. Highway 87 south for 29 miles you’ll find Comfort, a quaint, revitalized Texas town that’s home to Bending Branch Winery — worth a stop, if it’s late enough in the day for a delicious glass of red wine.

Continue 16 miles southeast to Boerne, another German-intoned town with a vibrant Main Street. Here, go on a shopping spree that must include homemade pickles from Fickle Pickles, which also sells beautiful antiques. Next, for a change of pace, venture 6 miles south on County Road 290 to Cascade Caverns, where you can honor your inner spelunker with an hour-long guided cave tour through five jaw-dropping natural rooms full of rock formations. Picnic (open those pickles) beside one of the on-site nature trails.

Drive 30 miles south on Interstate 10 to San Antonio, and check into your hotel (see below). If you’re planning a visit to the Alamo while in town, you’ll want to buy tickets in advance online. Later, dine at La Fonda on Main, a local favorite for Mexican food since 1932. Two menu standouts: oak-grilled fajitas and verdes enchiladas.    

Where to stay: Bunk at the 316-room Menger Hotel, adjacent to the Alamo and home to Menger Bar, where Teddy Roosevelt gathered with the Rough Riders in 1898.


an interior shot of the hotel emma in san antonio texas

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Hotel Emma is a refurbished former brewery, now a boutique hotel in the chic Pearl District of San Antonio

Day 5: San Antonio

Start the morning at the Pearl, an entertainment district within the bones of a sprawling 19th-century brewery complex. Located on the San Antonio River about 2 miles north of downtown, the district draws both locals and visitors with its shops, galleries, restaurants, boutique hotel and outdoor green spaces. If possible, schedule your visit for the weekend to coincide with a humming farmers market packed with vendors of every stripe. (On Saturday’s, you'll find food purveyors, and Sunday’s market is focused on crafts.) Whatever the day, eat breakfast at Bakery Lorraine, where French-trained bakers serve up fantastic macarons, almond croissants and croque madames (the French version of a ham-and-cheese sandwich, topped with a fried egg).

Four miles north, you’ll find the McNay Art Museum, set in a stately Italianate villa built by prescient art collector Marion Koogler McNay to hold her cache of 19th-century artwork. The first modern art museum in Texas is home to masterworks by the likes of Paul Cézanne, Georgia O’Keeffe, Pablo Picasso and Diego Rivera.

Austin-based travel writer Becca Hensley contributes to the New York Post, Travel + Leisure, Elite Traveler and other publications and websites.

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