September 9th, 2026
Your Fall Bucket List: Festivals & Markets Near Headwaters in Dripping Springs, Texas
There’s a certain kind of magic that settles over the Texas Hill Country once September rolls around. The days start to soften just a little, porch sitting gets even better, and the calendar fills up fast with festivals, markets, and live music. Whether you’re a longtime Headwaters neighbor or just getting settled in, fall is the perfect excuse to get out and explore everything Dripping Springs and the surrounding Hill Country have to offer. Here’s what’s on the docket this season.
Oktoberfest Party at Vista Brewing
Saturday, September 26 | Starting at 11 AM
Grab the whole crew – kids included – for Vista Brewing’s annual Oktoberfest celebration. Expect German-inspired eats, two brand-new brews, live music, and all the classic Oktoberfest games, including Steinholding and Hammerschlagen. Little ones can get in on the fun with pretzel necklaces, and yes, lederhosen and dirndls are absolutely encouraged. RSVP here.
September 26, 2026 | Downtown Bertram
A short drive from Headwaters, downtown Bertram will roll out nearly five decades of small-town charm for this beloved annual tradition. Expect a parade, live music, and plenty of family-friendly contests that make this festival a Hill Country staple year after year.
October 10-11, 2026 | Dripping Springs Ranch Park and Event Center
Now in its 14th year, this popular shopping event brings together a wide range of vendors offering clothing, home and holiday decor, jewelry, gourmet food, and Texas handmade goods. Admission is $6, or $5 with a non-perishable food donation – a great way to start your holiday shopping while giving back to the community.
Dripping Springs Songwriters Festival
October 16-18, 2026 | Downtown Dripping Springs
This free outdoor festival is one of the season’s must-attend events, drawing music lovers from across the region to local stages and venues throughout downtown. Featuring performances from a lineup of talented songwriters, it’s the perfect weekend to wander downtown, grab a bite, and soak in some live music under the fall sky.
Fredericksburg Food & Wine Fest
October 21-24, 2026 | Fredericksburg, TX
For those willing to venture a bit further, the Fredericksburg Food & Wine Festival offers a premier culinary and wine experience showcasing the best of Texas Hill Country cuisine, wine, and craft beverages. As a non-profit event, proceeds support charitable organizations throughout the region, celebrating the area’s agricultural heritage and award-winning wineries while giving back to the community.
And if you’re not already a Headwaters resident, while you’re out enjoying everything the season has to offer you should take some time to also explore the Headwaters community itself. Our final builder, David Weekley Homes, offers three distinct collections to fit every lifestyle: the Headwaters 50′ Executive Series, their brand-new 60′ Executive Series, and the final opportunities in their 80’ Executive Series. Each brings David Weekley’s signature quality and thoughtful design to the Hill Country, with homesites and floor plans to match however you want to live. There’s truly no better time of year to tour Headwaters – with cooler days, gorgeous views, and a community full of energy, fall is the perfect season to picture yourself calling this corner of the Texas Hill Country home.
Photo Credit: Fredericksburg Food & Wine
