A Staycation & Weekend Adventure in Dripping Springs, Texas

Dripping Springs, Texas has blossomed into a booming Hill Country city known as the “Gateway to the Hill Country” as well as “The Wedding Capital of Texas.” What started as a wagon train stop for water from a dripping spring turned into a ranch town with one stop light has turning into a popular tourist destination with 34 wineries, distilleries, and breweries; several excellent restaurants; lots of unique lodging; 35 beautiful wedding venues; and several fun things to see and do. Even though Dripping Springs has grown significantly, it still has that small Texas town feel and it’s loading with some of the friendliest folks we’ve met in a long time. We love Dripping Springs and can’t wait to come back for another visit!

We had a fantastic four-day staycation and weekend adventure in Dripping Spring sipping some wine and beer, enjoying some excellent restaurants, listening to a variety of music, and staying in some unique and cozy lodging. Unfortunately, we made a big mistake by staying in Dripping Springs on a Monday through Wednesday when a lot of the wineries and breweries were closed. Plus some of the bars and distilleries were permanently closed due to COVID-19 – but we still had a blast and now we have an excuse to come back again.

Some of highlights from our Dripping Springs staycation included:

• a flight of good beer, a German six piece band, and a great setting at 12 Fox Brewing
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  a delicious gourmet meal sitting next to a beautiful pool at Tillie’s restaurant
• a four night stay in cool casitas at Hill Country Casitas and a tree house at The Alexander at Creek Road
• a delicious four napkin cheese burger at Plough & Cooper
• socializing with some friendly and outgoing locals
• a wine tasting and tour of a very cool underground limestone wine cellar and winery at Hawk Shadow Winery
• a wide variety of music including karaoke, Texas country, German oompah, and a pickers’ circle.

Sippin’ in Drippin’

We love beer which meant that our first stop when we got to Dripping Springs was at 12 Fox Beer Company – a very lively spot with lots of families, live music, food trucks, and cold beer. We found a picnic table under the trees and enjoyed a flight of beer and a a conversation with Joe, one of the owners. Thanks to COVID-19, Joe has had to change the 12 Fox Brewing Company business plan four times so he could remain open. They evolved from a brewery to a bar to a grocery store and finally a restaurant. As we sipped beer, the six piece German band was playing some rousing oompah music and visitors were dancing, laughing, and having fun – the kids loved flipping their arms to the “chicken dance.” !2 Fox Brewing Company is a must stop if you like breweries – the setting is great, the food trucks have some good food, kids with love the playscape, there is always music on the weekend, the beer is very tasty, and the games they play on the weekend are lively and fun. For example, contestants have to manipulate a mug of beer hanging from puppet strings in front of them and take a sip.

12 Fox is just one of the reasons we decided to spend a few days exploring Dripping Springs which is quickly gaining a reputation as a craft beverage destination. The other 36 reasons are because Dripping Springs and its sister city Driftwood are home to 40 different places for “Sipping in Dripping.” That includes 12 wineries, 10 breweries, 7 distilleries, and 7 tasting rooms. Some are cool, downtown hangouts in the historic district of Dripping Springs, others are tucked away in the hills and off the beaten path, and some are eclectic retro-themed tasting rooms that scream mid-century nostalgia. I can’t think of a better place to sip! After our fun four days, we set a goal to come back and try at least half of them. And we’ll make sure that we get a Dripping with Taste Passport which is great way to experience Dripping Springs unique beverage scene. It is a wine, beer, and spirits trail plus a curated collection of great deals and discounts on some of the best craft beverages. For example, if you visit up to four of the participating wineries, breweries and distilleries in a single day you’ll receive up to 50% off one tasting or flight at each destination.

On Sunday, our first day in Dripping Springs, we sampled some fantastic beer at:

You can’t imagine how hard we searched to find other breweries that were open on Monday through Wednesday.. We also tried very hard to find one of the eight distilleries that might be open – several of which were permanently closed thanks to COVID-19 and others that were only open on Thursday through Sunday. When we found out that Tready Oak Distilling was open we rushed out there hoping to sample some of their whiskey, the Day Drinker Texas bourbon, or the Tready Oak Old Fashioned Cocktail. Nope – the distillery was closed but we did enjoy some very good BBQ and tap beer under the trees at their restaurant – Alices. Check out our new Dripping Springs Breweries Page.

We had the same problem with wineries – closed Monday through Wednesday. We even drove by several just to validate that they were closed – we were getting desperate! When we told Mary, the owner of Hill Country Casitas our dilemma, she called a nearby winery and set up a tour and tasting for us, even though they were closed on Mondays. We thanked her profusely put on our drinking hat and rushed out to met the owner of Hawk’s Shadow Winery.

Wow, what a fantastic setting on a bluff overlooking one of their vineyards and several miles of beautiful breathtaking Texas Hill Country. We met with Doug Reed, the owner of Hawk’s Shadow Winery (best known for handcrafted Texas wine) and he allowed us to sample some of the white wines – our favorite was the 2017 Juliet which expresses “fresh and botanical attributes fused with a core element of granny smith apple, shows elegant floral notes embolden with green apple peel, and a strong mineral core and it had a finish that was clean but lingers with a wild honey and citrus finish for minutes.” I read that off the label and I don’t know what it means, but I do know I sure liked the taste of Juliet! Some of the things we learned about Hawk’s Shadow Winery that make them unique are that:

• after a couple of years and a lot of hard work tilling the limestone soil, they were able to finally harvest fine wine grapes from a barren rocky hilltop
• they are one of the few gravity flow wineries which contributes to making a better tasting wine
• they carved a very cool underground solid limestone cave and turned it into a wine cellar that is a constant cool temperature and also helps with aging

We had some free time during our search for an open drinking spot and just happened to drive by Texas Hill Country Olive Company and decided to check it out. From a stunning Tuscan inspired venue they provide fresh locally produced extra virgin olive oil, barrel aged balsamic vinegar, and other premium quality products. From a whole wall of balsamic vinegars I had to buy the Raspberry Balsamic Vinegar and a jar of Habanero Stuffed Olives – I’m tasting some of that fire!

If you visit Dripping Springs make sure you take a wine tasting tour at Hawk’s Shadow Winery. And give some of the other Dripping Springs and Driftwood wineries a try.

Dinin’ in Drippin’

Although we had a problem finding wineries, breweries, and distilleries that were open, we didn’t have any trouble finding some great places to stuff our tummies! Just some of the restaurants that we loved included:

• a delicious 5 napkin juicy cheese burger at Proof & Cooper and some good BBQ at Alices at Treaty Oak
• a couple good sandwiches at the cute and funky Rolling in Thyme and Dough
• a delicious breakfast of eggs over easy and migas at El Rey Mexican Bar & Grill
• a lot of calories from the deviled eggs, mac & cheese, and huge chicken fried chicken diner at Homespun Kitchen & Bar
• music and a very good pork chop at what was a gas station in the ’80s and is now restaurant and large outdoor bar and patio under the trees at Hays City Store

During the first few days of our visit we ask lots of locals what they considered to be the best restaurant in Dripping Springs. At the top of everyone’s list was Tillie’s at Camp Lucy. So for our last night, we booked a reservation and enjoyed a beautiful setting and one of the best meals we’ve had in a long time. You’ve got to read our article on dining at Tillie’s. My mouth is watering just thinking about our dinner at Tillie’s!

Singin’ in Drippin’

In additions to restaurants, we didn’t have any problem finding live music to enjoy each evening. Here’s a quick summary of what we found and loved:

• it started with live music at 12 Fox Beer Company from the six piece sax-centric German Reed Meisters playing oompah Octoberfest music
• cold beer and a picker’s circle with 6 very talented musicians (playing guitars, fiddles, a thrump, and a box drum) on the patio of the Barbershop was outstanding and fun – located in the historic district the Barbershop started as a garage and gas station in 1938, then became a barbershop for 25 years, and now its a no frills beer and wine bar
• a lively and friendly crowd dancin’ and drinkin’ to a fun country western band at Mercer Dance Hall
• W. C. Clark Blues Revue (the multiple award wining Godfather of Austin Blues for 60 years).playing sophisticated uptown blues, rhythm, and groove at the outdoor stage at Hayes City Store
• some interesting karaoke music at Hudson’s on Mercer Street

If you like music, make sure you check out the Dripping Springs Visitor Bureau website which does a great job of posting events and live music.

Sleepin’ In Drippin’

After all that eating and drinking and music, we needed a good night’s sleep and we got it at Hill Country Casitas for two nights and The Alexander at Creek Road for two nights. We were very impressed with both places and would highly recommend that if you’re planning a weekend getaway or staycation that you seriously consider them for lodging.

Hill Country Casitas is located on 13 beautiful acres of rolling Texas Hill Country a few miles north west of downtown Dripping Springs. They have eleven custom built new one and two bedroom Casitas that opened in October 2016 plus a three bedroom Ranch House. All of the lodging is very well appointed and sparkling clean and equipped with everything that you need for an enjoyable weekend. And I had a very hard time getting out of the Serta Plush mattress to start another day of exploring Dripping Springs. They also have a cool pool, hammocks in the grotto, hiking trails, unbelievable views and sunsets, and meeting/wedding space. Read more about Hill Country Casitas and why we highly recommend them.

We hated to leave Hill Country Casitas but we were equally impressed with The Alexander at Creek Road which sits on 40 acres of peaceful and quiet (except for the crickets, owls, and an occasional moo under the dark night sky) in a beautiful gently rolling country setting – a “piece of heaven” is the way one visitor described it. Lodging options include: The Country House (3 bedroom/3 bathrooms and sleeps 10), 4 unique and cozy cabins/cottages, plus the Treehouse Complex. We stayed in one of the 4 suites in the Treehouse Complex and absolutely loved it – read our article about a stay in the Treehouse Complex at The Alexander at Creek Road.

Other Fun Things To Do In Dripping Springs

There is a lot more to Dripping Springs besides just drinkin’ and sippin’, good food, excellent lodging, and music – some of the other fun things to see and do during a visit to Dripping Springs include:

• over 270 acres set aside in four different parks for outdoor activities like hiking, mountain biking, birding, picnicking, horseback riding, star gazing, swimming, baseball, football, soccer, lacrosse, sand volleyball, and more
• a drive-in movie theater under the stars, away from the city lights, and surrounded by beautiful trees
• Hamilton Pool which is a beautiful and unique swimming hole
• Dreamland which is an outdoor entertainment and arts venue that features the world’s most extreme miniature golf course, four premium weather-protected pickleball courts, a beer garden, and two state of the art music stages plus large scale sculptures
• a unique driving range at Dripping Springs Country Club with Top Golf Technology plus food, drinks, and merchandise

Westcave Outdoor Discovery Center is also a must visit if you’re in Dripping Springs. It’s a box canyon grotto covered in native ferns with water dripping over the elevated concave wall into Heinz Branch Creek, which creates an emerald green pool that is 20 feet deep. A paid guided tour is required to hike into the grotto

Reimers Ranch Park is 2400 acres of undeveloped land with more than 18 miles of scenic trails for mountain biking, three miles of frontage along the Pedernales River for fishing and swimming, and lots of rock climbing spots – in fact, Reimers Ranch Park is a world class destination for rock climbing.

Pedernales Falls State Park is close by and it’s one of Texas Outside’s favorite state parks – there are 21 miles of hiking trails; a quarter mile nature trail; 20 miles of bike trails; a 10 mile equestrian trail; a beach with river swimming; and fishing primarily catfish) along the banks of the river.

Dripping Springs is known as the “Wedding Venue Capital of Texas” thanks to over 40 beautiful wedding venues in Dripping Springs and nearby Driftwood that are perfect for a memorable, unique, and fun wedding. .

Make sure that you plan a trip to Dripping Springs during one of their famous special events like the Dripping Springs Songwriter’s Festival, Founders Day Festival, or the Dripping Springs Fair & Rodeo. You’ll find the events on the Dripping Springs Visitors Bureau Website.

Texas Outside’s interactive map of Dripping Springs has a lot of the above and more, plus our Top 10 Favorites..

Have fun – I’m sure you’ll fall in love with Dripping Springs like we have. We can’t wait to get back.

Author: Mike Sharp

I have a passion for travel and outdoor activities, and now I'm enjoying retired life. I will continue my traveling, golfing, boating, and enjoying life all across the great state of Texas.