Hill Country Highlights: Your Guide to October’s Can’t-Miss Events

October is a special time in the Texas Hill Country, when the air cools down and local festivals bring together music, history, and plenty of good food. If you’re looking for an authentic taste of Hill Country charm, these three events will give you the perfect reason to take a weekend road trip. From intimate songwriter performances to rich frontier history and a Texas twist on a German festival, you’ll discover the heart and soul of this beautiful region.

Dripping Springs Songwriters Festival: Personal Stories in Every Song

Oct. 18-20

Downtown Dripping Springs, 311 Old Fitzhugh Road

If you’re a fan of authentic music and small-town charm, the Dripping Springs Songwriters Festival is the place to be. Over 35 songwriters will take to seven different stages, sharing their personal stories through music. This isn’t your typical concert—here, the artists perform “in the round” in Nashville-style song swaps, where they take turns playing and explaining the inspiration behind their songs.

You’ll feel like you’re sitting in someone’s living room as musicians open up about their journeys, challenges, and inspirations. The beauty of this festival is in the connection between artist and audience—each performance feels personal, like you’re getting a sneak peek into the mind of a songwriter.

The best part? All of the downtown shows are free, making it easy to pop in and out of different venues throughout the day. Take a leisurely walk along Old Fitzhugh Road, enjoy a cup of coffee from a local café, and let the melodies guide you through the weekend. Don’t forget to take in the Hill Country scenery—Dripping Springs is known for its rolling hills and stunning vistas, so every moment here feels like a mini escape.

Pro Tip: Plan to arrive early to snag a good spot at one of the smaller venues. This is a more intimate festival, and seating can fill up quickly at the popular spots.

More info

Llano Heritage Days: Step Into the Past

Oct. 18-20

Badu Park, 300 Legion Drive

For a real taste of Texas history, head to Llano Heritage Days, where you’ll feel like you’ve stepped back in time. This weekend-long event brings to life the rich frontier history of the area with living history actors, cowboy poetry, and traditional music. It’s a family-friendly festival that mixes education with fun, giving you a glimpse into what life was like in the early days of the Hill Country.

Friday night kicks off with a classic chuckwagon supper—an event that will take you straight into the heart of Texas cowboy culture. You’ll gather around the campfire, listen to cowboy songs and poetry, and enjoy hearty dishes prepared in traditional chuckwagon style. It’s an experience that brings a little slice of the Old West to life.

On Saturday, the festival hits full stride with a wide range of activities. Watch blacksmiths and artisans at work, browse a vintage quilt show, and marvel at the gleaming Model A cars on display. The festival also offers live music, games for kids, and an opportunity to learn about Llano’s history through interactive exhibits and living history demonstrations.

Sunday wraps up the weekend with something truly unique—a living history cemetery tour. Local actors portray the town’s early settlers, sharing their stories as you stroll through Llano’s historic cemetery. It’s a fascinating way to connect with the people who shaped the town’s past.

Pro Tip: Bring your walking shoes—Badu Park is spread out, and there’s a lot to see and do. Take your time exploring the festival’s different areas, and be sure to check the schedule for special performances and demonstrations throughout the day.

More info

Fredericksburg Bestfest: German Flavor with a Texas Twist

Oct. 19

Marktplatz Pavilion, 100 W. Main St.

If you love a good German festival, Fredericksburg’s Bestfest is a can’t-miss event that brings together the town’s rich German heritage with a Texas-sized celebration. Hosted by the Knights of Columbus, Bestfest offers an all-you-can-eat sausage meal that’s worth the trip alone. Expect specialty sausages like bratwurst and knockwurst, served up with all the classic sides—sauerkraut, mustard, and pretzels.

As you enjoy your meal, the festival really kicks into high gear with live polka and country bands providing the soundtrack for the day. There’s plenty of space to dance, and whether you’re a seasoned polka pro or just want to tap your feet to the beat, you’ll feel right at home.

Beyond the food and music, Bestfest offers plenty of opportunities to test your luck. There’s a multi-gun raffle, a Kawasaki mule raffle, and several bucket raffles with prizes ranging from local crafts to outdoor gear. The event also includes activities for kids, making it a great family outing.

Located in Fredericksburg’s charming Marktplatz Pavilion, the setting couldn’t be more perfect for this lively celebration. As you take in the sounds and flavors of Bestfest, you’ll be surrounded by Fredericksburg’s iconic Main Street, where you can explore shops, grab a local brew, or just relax in the town’s welcoming atmosphere.

Pro Tip: Arrive early to get your fill of sausage and snag a good spot near the dance floor. And if you’re feeling lucky, don’t forget to enter the raffles—this festival has some of the best prizes in the Hill Country!

More info

Whether you’re looking for a weekend of music, history, or simply a great meal, the Texas Hill Country offers something for everyone this October. Dripping Springs, Llano, and Fredericksburg each provide a unique glimpse into the region’s culture and charm, making them perfect destinations for your fall adventures.

So pack your bags, hit the road, and get ready to discover the heart of Texas—one song, story, and sausage at a time!

Stay Connected with Us

Thank you for joining us on this journey through Texas Hill Country. We hope you enjoyed discovering the hidden gems and unique experiences this beautiful region has to offer. Stay tuned for more insights, travel tips, and local spotlights in our next edition. Don’t forget to share your Hill Country adventures with us!

Jeremy

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