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Three Awesome Days in the Canyon Lake, Texas and the Heart of the Texas Hill Country

If you’ve even half-heartedly glanced at my social media then chances are you have noticed I have a soft spot for live music. And the Texas Hill Country. And live music in the Texas Hill Country. Throw in a luxurious stay overlooking Canyon Lake? Even better.

So when I found out that Chris Stapleton was playing at River Road Ice House in New Braunsfels, Texas, I knew I was gunna be there come hell or high-water.

Luckily Mr. Gypsy’s birthday was coming up, giving me just the excuse I needed to turn this concert into the start of a birthday weekend blow-out. Enlisting the help of a fellow gypsy (who happens to be a Texas Hill Country connoisseur), we put together a classic Texas Hill Country bucket-list weekend itinerary.

the pool and Skyhouse overlooking Canyon Lake
The pool of Skyhouse overlooking Canyon Lake

Day 1 in Canyon Lake


Making good time we opted to kickstart the festivities with a few cold craft brews before checking into our Airbnb. Consulting my Hill Country Craft Beer Trail map, we decided on Middleton Brewing in San Marcos since it wasn’t far.

I knew when we walked in that even if I didn’t care for the brews, Middleton already won my heart. Three fat and wrinkly pugs waddled up to greet us. Dogs and beer. Life IS good.

pug at Middleton Brewing
One of the pug greeters at Middleton Brewing in San Marcos

The best way to sample Middleton’s beers, start with a flight board of five beers of your choice. I savored some brews of the darker variety, such as the U.S. Beer Open Gold Metal Winner Black Lab Porter (Ok, ok I ordered it because of it’s name…I only noticed it had won a medal later on.)

Middleton Brewing beer flight
Assorted craft beers in Middleton Brewing beer flight

I also partook in the U.S. Beer Open Bronze Medal Winner Tourmaline, the barrel aged Raspberry Porter (which tasted of, you guessed it, raspberries), the Garnet Belgian Amber, and (for the sake of diversity) the Easy Rider Pale Ale.

Our Airbnb in Canyon Lake

Finishing our brews, it was time to check in our Airbnb in Canyon Lake. 

We wound our way steadily up curvy, switchback roads to the top of a hill where the SKYHOUSE clung to the steep side of the rocky hill overlooking Canyon Lake and the surrounding hill country.

The clean, contemporary profile of the house was a pleasant contrast to the rolling, rocky landscape surrounding Canyon Lake. The galvanized tin that wrapped the exterior was softened by the feathery grasses and chaparral that covered the hillside.

view from the living room of Skyhouse
Check out that View of Canyon Lake!

Inside was bright and airy due to the high ceilings, open floor design, and floor-to-ceiling windows that opened onto the wraparound viewing deck. State-of-the-art appliances, gorgeous orange granite, and highly polished wide plank floors were artfully balanced with exposed brick, open live-edge shelling, and bright and cheery furniture.

living room of Skyhouse
180 degree view of Canyon Lake from Skyhouse’s living room

Downstairs, the locker and exposed I-beam hinted at an industrial vibe while large windows rivaled the view upstairs. In a word AWESOME! And it was just minutes from New Braunsfels and Gruene!

Master bedroom with view of Canyon Lake
View from master bedroom of Skyhouse overlooking Canyon Lake

Live Music in Texas Hill Country

Situated far from city lights, at the corner of River Road and Hueco Springs Loop, sits River Road Ice House. Surrounded by the rolling hills of central texas and open to the stars, this place presents the ultimate Hill Country live music experience.

A large outdoor stage rests at the bottom of a sloping hill where tiers of foldout chairs made up part of the reserved section. At the top of the slope were beer booths and food vendors.

To the right of the outdoor stage is the icehouse. Here, a garage door rolls up revealing a smaller stage, where the memorabilia is sold, and more bars. On top of the icehouse is the VIP section overlooking the stage and the hill.

Pro TIP: If you are attending an outdoor concert… in Texas…in the summer…forgo trying to look too cute. You are going to be standing a looooong time so ditch the heels. You are going to sweat profusely, so don’t bother with a lot of makeup. Guys, steer clear of heavy denim and starched button downs unless you bought stock in Goldbond. Stick with comfortable, breathable tees, tanks, and shorts. Trust me, no one will think less of you!

We claimed a grassy seat just behind the reserved section, a couple of drinks, and a burger from one of the onsite food vendors. The sun began to set and thankfully a breeze picked up as the Quaker City Night Hawks hit the stage to a heavy rock and roll beat.

Concert at River Road Ice House
Live music under the stars at River Road Ice House

By the time Chris Stapleton took the stage, the night had cooled off and the stars shone brightly overhead. He sounded even better live than he does on his albums. Between songs he spoke of the stories and situations behind his songwriting. Overall, an incredible concert.

To top the night off, as we walked back to the trucks, the owner of the field in which we parked in had set up a giant BBQ pit and was handing out ribs and roasted corn to everyone.

Man, I love Texas.

Day 2 in New Braunfels

Floating the Guadalupe

The day dawned clear and bright, perfect weather for a day spent leisurely floating down the Guadalupe River. Just a few minutes from Canyon Lake you will find several outfitters ready to rent you a tube. They’ll even rent you one for your ice chest.

They also conveniently shuttled you to the water and picked you back up at the end of the day.

Running through the middle of New Braunfels, the Guadalupe, or “Guad”, is a favorite by both visitors and locals alike. As the summer temperatures soar into triple digits, the cold waters of the spring-fed river offer much-needed respite. From tubing to fly-fishing, the Guadalupe remains a major feature in the Texas Hill Country playground.

The Guadalupe River in New Braunfels
The beautiful Guadalupe River in New Braunfels

For most of the day, we leisurely floated beneath the low-hanging cypress boughs in the clear, cold river. After reaching our pick-up point, the outfitters shuttled us back to our cars in the heart of Gruene.

We returned to Canyon Lake and SKYHOUSE where we grilled, stayed up late into the night swimming in the pool, and watched the Perseid meteor shower. The stars at night truly are big and bright deep in the heart of Texas Hill Country.

Day 3 in Gruene

Our last day dawned overcast with the sound of rumbling thunder in the distance. Slightly cooler, conditions were ideal since we planned on spending the day walking around the Waterpower District of Gruene.

Gruene Hall
Texas’ Oldest Dance Hall, Gruene Hall

Founded in 1845 by German immigrant farmers, Ernest and Antoinette Gruene, their estate prospered due to cotton yields. Eventually 20 or more families moved to Gruene where Ernest and his sons had already built several homes resulting in a mercantile store and a cotton gin.

Soon a dance hall was built shortly followed by an additional general store. The boll weevil eventually wiped out cotton crops and the Great Depression finished off what the boll weevil hadn’t.

Except the dance hall. It never closed. In the 1970’s, the entire town of Gruene was registered in the National Register of Historic Places.

Listening to Live Music at Gruene Hall
Listening to Band of Babies at Gruene Hall

Boutiques and small businesses moved into the original homes and mercantile stores and The Gristmill River Restaurant & Bar moved into the hull of the original cotton gin.

To this day Gruene Hall still offers live music all day, everyday of the year in the same dusty, unairconditioned building.

We browsed through Blank Swan Antiques, taste tested the homemade salsas in the Gruene General Store, and picked out a few pieces of pottery at The Barn Pottery.

We even ventured into Pookie Jane’s, a woman’s apparel boutique boasting the “Man Cave” with free beer and TV.

More Live Music

Gradually we made our way into Gruene Hall for a beer and a song. Long wooden tables carved and graffitied over the years lined the floor. A cash bar serves cold beer and drinks to sweaty patrons who wonder in and out throughout the day.

Gruene Hall Drink Menu
Cash Bar at Gruene Hall

Once the band took a break we headed to The Gristmill for a late lunch/early dinner . With 10 different dining “rooms”, The Gristmill is easily the biggest and most famous restaurant in town. Structural elements such as collapsed brick walls, dark exposed beams, and large industrial chains are constant reminders of the buildings original function.

cocktails at The Gristmill in Gruene
There’s never a bad time for margaritas at the Gristmill
Pulled Pork sandwich at The Gristmill
The Gristmill’s pulled pork sandwich is a thing of beauty

Close to bursting, we heading back to SKYHOUSE ladened down with our purchases. Our last night was spent once again on the wraparound deck and in the pool overlooking the twinkling Texas Hill Country.

Night swimming at Skyhouse Canyon Lake
Swimming after dark in Canyon Lake’s Skyhouse pool

If you are considering a trip to the New Braunsfels area of the Texas Hill Country and are interested in the SKYHOUSE, you can visit their find them Airbnb. (Psst…if you’ve never used Airbnb, use my Refer a Friend Link for up to $65 off your first stay!)

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Jessica Pickett

Gypsy mom, storyteller, and daydreamer extraordinaire, you can usually find me researching our next adventure. An explorer, lover of craft beers, and anything outside I'm at my happiest getting lost in a new city or hitting the trails with my family in tow.

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