This Epic Texas Road Trip Visits Underrated Vineyards and Rolling Hills Blanketed in Bluebonnets

Texas Hill Country is one of the most beautiful stretches of the Lone Star State, and its impressive wine scene is only growing.

Curving roadway and Texas Bluebonnets with Enchanted Rock in the distance
Photo: Marc Bennett

From early spring well into early winter, there is always a great time to take a weekend trip through Texas Hill Country — home to some of the most stunning landscapes in Texas.

This vast, rural region of south-central Texas is conveniently close to all major cities. Its rolling hills are only an hour-long drive from Austin and San Antonio and a four-hour jaunt from Dallas and Houston. You will not have an easier day trip in the largest continental state in the country.

The hills dotted with sprawling cypress and oak trees make for an idyllic road trip route that's especially picturesque in spring and fall. Some of the lushest fields of bluebonnets bloom in spring, and there's nothing more Texan than a bluebonnet photograph.

The main attraction of the region is no longer a secret — Texas Hill Country has become widely known as Texas Wine Country. In fact, Texas is the fifth-highest wine-producing state and is home to the fifth-highest number of wineries, according to data from Texas wine isn't new, but it is rapidly growing, and the quality is only getting better as growers perfect the grapes that do best in the rocky Texas soil.

Curving roadway and Texas Bluebonnets with Enchanted Rock in the distance
Marc Bennett

There are a few noteworthy towns along Highway 290, better known as the Texas Wine Trail, where you will find numerous vacation rentals and historic hotels. Some newer and noteworthy rental accommodations to book are Honey Tree Farm for a real treehouse experience, A-Frame Ranch for tucked-away luxury cabins, and Blue Skies Retro Resort for incredibly fun vintage trailer stays. For a true luxury experience with zero hassle, book a stay at La Cantera Resort & Spa, a Travel + Leisure World's Best Awards winner outside of San Antonio, and their concierge will plan a wine country tour day trip for you.

An A Frame Cabin at A Frame Ranch in Texas Hill Country
Courtesy of A Frame Ranch

When it comes to touring wineries, there are bus and limousine tours, of course, but for a more intimate experience, designate a driver to achieve the real road trip vibe. (Drivers should be weary of the abundant deer population along the roadway.) From Dripping Springs to Fredericksburg, the wineries and distilleries are in such abundance, planning can quickly become overwhelming for the first-timer.

The best route to choose is based on wine preference, notable wineries, and approximate distance to your booked accommodation. The Texas Vintners Cup is a solid start for selecting award-winning wineries.

Vineyard and welcome center building at William Chris Vineyards in Hye, Texas
Mariah Tyler
Exterior building signage and tasting pour at Lost Draw Cellars in Fredericksburg, Texas
Courtesy of Lost Draw Cellars

Lost Draw Cellars and Slate Theory Winery are in Fredericksburg and offer tastings by reservation. Out on the wine trail, in Hye, Texas, William Chris Vineyards boasts panoramic views of Hill Country from its stunning modern welcome center and Hye Society Wine Club. The new building opened in 2019, and the wine tastings in the library offer a delectable crash course in Texas wines. From learning about the best Texas-grown grapes to sampling the best vintages available, the expert-guided tasting is a valuable experience.

View of Main Street in Fredericksburg, Texas
Rhiannon Taylor

Back in the town of Fredericksburg, take a stroll down Main Street, where you can sip wine and beer while you shop. With a long history of German influence, Otto's German Bistro is the best place in town for a Texas German dinner. For the brunch lovers, Hill & Vine offers a unique brunch menu with black-eyed pea hummus and peachy pecan pancakes. Short on time and need a bite to go? Hye Market and Deli has delicious sandwiches, perfect for lunch in between tastings.

View from Enchanted Rock at Enchanted Rock State Park in Texas
Mariah Tyler
Table seating on a hillside of an Airbnb rental outside of Fredericksburg, in Texas Hill Country
Mariah Tyler

Nature enthusiasts can experience Pedernales Falls State Park and Enchanted Rock State Natural Area — each one has options for anyone who loves to hike, swim, and even ride on horseback. Texas Hill Country, with its winding roads and hilly vistas of live oak trees and prickly pear, is one of the most scenic places in the Lone Star State and offers some of the best wines east of California.

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