Jenny Cureton Real Estate | Dripping Springs • Wimberley • Fredericksburg

January in the Texas Hill Country is one of the best kept secrets. The crowds are lighter, the weather is usually comfortable for exploring, and you can actually enjoy the towns without fighting weekend traffic. If you are living in Dripping Springs, Wimberley, or Fredericksburg or planning a Hill Country relocation, here are some of my favorite January activities.

1. Go for a winter hike and actually enjoy it

This is the month to get outside. Try an easy morning hike, then reward yourself with coffee and a slow lunch. Winter is also a great season to explore state parks and river areas because the trails are less crowded and the temperatures are more comfortable for longer walks.

2. Do a Polar Bear Plunge in Wimberley

If you want something classic and very Wimberley, the annual Polar Bear Plunge and 5K at Blue Hole Regional Park is a fun way to start the year.

3. Spend a day in Fredericksburg for the Book Festival

Fredericksburg is perfect in January because it still feels lively, but not packed. The Fredericksburg Book Festival happens on Saturday, January 17, 2026 with author talks, book signings, and activities in multiple locations around town. Book Festival Info.

4. Catch trout stocking season and go fishing

Winter trout stocking runs through early March 2026 and includes Hill Country spots, including locations in Fredericksburg and the Guadalupe River area. If you have kids or you want an easy outdoor day that is different than wineries, this is a great January plan. More details.

5. Make it a Dripping Springs brewery and winery day

Dripping Springs is built for a laid back tasting day. January is a great month to do it because it is less crowded and more relaxed. For visitors and locals, Destination Dripping Springs keeps an events guide that is helpful when you want something going on that weekend. Dripping Springs and Driftwood Wineries and Breweries. Fredericksburg Wineries and Breweries. My favorite Wineries are Signoir Vineyard and Untamed Winery.

6. Check what is happening at Dripping Springs Ranch Park

If you have kids or you like community events, the Ranch Park calendar is worth checking. It includes January events like the Hays County Livestock Show scheduled for January 19 and 20, 2026.

7. Plan a Fredericksburg New Year walk

If you want a healthy reset vibe to start the year, Fredericksburg has a New Year’s Day walk event listed on the city calendar.

8. Do a small town live music night in Wimberley

Wimberley has a strong local music and arts scene year round, and January is a great month to enjoy a show without the busier spring crowds. One example is a Wimberley Players special event listed for January 24, 2026.

9. Take a one day Hill Country loop from Austin

A simple day trip loop that includes Dripping Springs, Fredericksburg, and Wimberley is a perfect January itinerary. Austin’s tourism site highlights Hill Country day trip style exploring, which is exactly what January is great for.

My January recommendation if you only do one thing

Pick one outdoor activity in the morning, then do a long lunch and a small town stroll. January is the month where the Hill Country feels the most relaxed and livable. Looking for some great restaurant recommendations? I enjoy Hays City Store in Driftwood, Nada Mucho in Wimberley and Hill and Vine in Fredericksburg!

If you are relocating and want help choosing between Dripping Springs, Wimberley, and Fredericksburg based on lifestyle, commute, and what your weekends will actually look like, reach out through my Contact page and tell me what you want your daily life to feel like.