Hill Country Cheers: Three Ways to Spend Labor Day Weekend in Boerne
August 29 – September 1, 2025
1. Kendall County Fair & Parade
August 29–31 • Kendall County Fairgrounds and Main Street
Now in its 119th year, the Kendall County Fair blends old traditions with new energy. The rodeo brings bull riders and barrel racers into the ring, while mutton-bustin’ and carnival rides light up the evenings for the kids. Live performances from artists like Coffey Anderson and Glen Templeton set the soundtrack.
On Saturday morning, the parade rolls down Main Street at 10 AM, a colorful procession of floats, marching bands, and the Fair Queen’s court. Families line the sidewalks, children dash for candy, and the whole town seems to show up to cheer.
Location: 1307 River Rd & along Main Street, Boerne
Details: kcfa.org
2. International Bat Night – Guided Walk
Friday, August 29 • 8:00–9:00 PM • Guadalupe River State Park
As twilight falls, the Guadalupe River State Park becomes a classroom without walls. With the help of bat detectors, you’ll listen for the high-frequency calls of Hill Country bats and watch them dart across the sky on their nightly hunt for insects.
The walk is both informative and atmospheric—part science, part summer-night magic. It’s a reminder that even after the sun sets, the Hill Country has its own kind of energy.
Location: Amphitheater behind the Discovery Center, Guadalupe River State Park
Details: boernelove.org
3. Labor Day at Lost Oak Cellars
Monday, September 1 • 12:00–8:00 PM (Live Music 2:00–5:00 PM)
Labor Day deserves a slower pace, and Lost Oak Cellars delivers. Their shaded patios will be open all day, serving wines, sangria, and the ever-popular winearitas. The afternoon soundtrack is provided by Daniel Johnson, whose live set runs from 2 to 5 PM.
It’s the kind of setting that encourages lingering—conversations stretch out, glasses are refilled, and the Hill Country sky takes its time changing colors.
Location: Lost Oak Cellars, Boerne
Details: lostoakwinery.com
Quick-View Schedule
| Event | When | Where | Link |
|---|---|---|---|
| Kendall County Fair & Parade | Fri–Sun, Aug 29–31 Parade: Sat, Aug 30 • 10 AM |
Kendall Co Fairgrounds & Main St, Boerne | kcfa.org |
| International Bat Night – Guided Walk | Fri, Aug 29 • 8–9 PM | Guadalupe River State Park | boernelove.org |
| Labor Day at Lost Oak Cellars | Mon, Sep 1 • 12–8 PM Live music 2–5 PM |
Lost Oak Cellars, Boerne | lostoakwinery.com |
Closing Note
This weekend offers a balance of energy, curiosity, and rest. The fair connects us to community traditions, the bat walk highlights the natural world at our doorstep, and the winery provides space to slow down. Three ways to make the most of the long weekend.
