Hello everyone & happy Friday! I have been so excited gathering all of the details of Jordan & I’s anniversary trip to Fredericksburg, TX to share with you all. I hope y’all enjoy this 4-day guide in the Texas Wine Country!
Now grab your coffee, tea, or especially wine for this one (😉) & get to reading:
We made our way into town early Friday afternoon and our very first stop was at Hye Market for some grub. This place had a cute, old town feel with tons of live chickens walking around near the outdoor patio, which I was very excited about. I have a dream of Jordan and I having our own chickens & farm-fresh eggs one day.
Jordan and I split The Market Italian that was served on a delicious Italian Herb Focaccia Loaf before making our way to the next destination.
Next up on the agenda was a tour of the Garrison Brothers Distillery. Neither Jordan or I are typically bourbon drinkers, but it was very interesting being able to learn how bourbon is made, learn about the Garrison Brothers company/story, and how to drink bourbon. I highly recommend giving this tour a shot. The distillery is only 25-30 minutes away from downtown Fredericksburg & the tour only lasts about 1-2 hours, but you soak in so much information and have a great time doing it! We actually had the founder of Garrison Brothers as our tour guide, which made the experience even better.
P.S. Shout out to our friend, Justin, for getting us these tour tickets as a wedding gift last year!

Once we made it into downtown Fredericksburg, we got checked into our room at The Inn on Barons Creek. The hotel was quaint and had everything we could have needed for our stay including a beautiful creek/forest view, king size bed, living area, and a nice-size bathroom with a jacuzzi tub. This hotel is also a short walk to Main Street where you will find majority of the restaurants, shops, and bars.
Jordan and I walked about a mile from the hotel to enjoy some amazing pizza & calzones at West End Pizza Co. This pizza place had been recommended by quite a few people so we knew we had to check it out. I would recommend getting there early on a Friday to grab a spot on the outdoor patio. I ordered their BBQ Chicken Pizza & Jordan created his own calzone with Alfredo sauce, mozzarella, ricotta, pineapple, spinach, and bacon. The food was delicious!
After a very full day & bellies, Jordan and I called it a night pretty early to prepare for an eventful Saturday. We ended our night watching the latest episode of “The Mandalorian” at the hotel.
We grabbed coffee & breakfast at the Java Ranch Espresso Bar & Cafe on Saturday morning and this place quickly became our go-to for the rest of the trip. We split a potato, egg, and cheese breakfast burrito & I ordered a peppermint mocha latte while Jordan enjoyed an iced white chocolate mocha. Their coffee was the bomb!
Saturday was for the wineries! I had so much fun putting together a cute outfit for this day. I found this super comfy dress on sale at American Eagle the week before we left, my favorite pumpkin-colored hat is from Anything Bling Boutique, the black booties are from Tom’s, and my long, rose gold pendant necklace is from Kendra Scott. Some of these pieces are a couple years old (except for the dress), but you can still find very similar items at each of these shops.
We booked the 290 Wine Shuttle for Saturday, which was one of the best decisions. You pay $29.99 per person (or get a 20% discount if you stay at The Inn on Barons Creek) to be shuttled around from 10am-6pm to all of the vineyards and wineries on their route. Some of the vineyards require reservations on the weekends, so make sure you look into that while planning your trip. The shuttle picks you up from The Inn on Barons Creek and makes a loop around several wineries & vineyards along 290. They have shuttles picking you up at each winery or vineyard every 10 minutes, so you never have to wait long when you’re ready to head to your next destination.
We made reservations at the Barons Creek Vineyard for our first wine tasting of the day. It took us roughly 20 minutes to get there from the hotel pick-up. This vineyard was very quiet, sophisticated, and had a touch of Tuscany in their architecture. The staff was very friendly (we had Sandy as our server and she was awesome) & the wine was great. Jordan & I split the red wine tasting & then each got a glass of a couple of our favorites, but it was so hard to choose. We both loved their Crazy Train Merlot and decided to buy a bottle of it to take home with us.
Our next reservations were at the Messina Hof Hill Country Winery. Most Texans have heard of Messina Hof. I actually drank Messina Hof Beau our entire wedding night, but actually going to their winery, talking with the staff about their different wines, and being able to try wines that are exclusively sold at their Fredericksburg location was such a neat experience. Jordan and I each did their standard tasting, which comes with 5 tokens. Each standard glass of wine equals 1 token and their premium wines equal 2 tokens. As soon as we sat down we were presented with complimentary glasses of Pinot Grigio & we devoured some delicious spinach and artichoke dip.
For the tastings:
I tasted the GSM ‘18 & Tempranillo, Private Reserve ‘18 on the Dry Red Wines list. The Heavenly Hill on the Semi Sweet Style Wines list & the Bonarrigo Heritage Reserve ‘18 on the Premium Wines list. Every single glass I tried was great, but my top 2 were the GSM ‘18 and the Bonarrigo Heritage Reserve ‘18.
Jordan tasted the Cabernet Franc, Private Reserve ‘18, the GSM ‘18, & Sagrantino Reserva ‘18 on the Dry Red Wines list. He also tried a couple of very good ports. He tried the Tawny Port & the HC Black Label Port ‘17, which is only sold at that specific Messina Hof Winery.
We decided to purchase a bottle of the GSM ‘18 and the HC Black Label Port ‘17. We both loved the GSM ‘18 & Jordan thought the port would be a nice drink to have while we enjoyed our occasional cigar together.
P.S. don’t forget to request JR Sanchez as your server. He was extremely informative, was very knowledgeable on which wines he thought we would each like best, gives great analogies on each wine, and has a fun sense of humor. Jordan and I both very much enjoyed our time at the Messina Hof Winery.
Fat Ass Ranch & Winery was our last winery for the day. This place definitely gets an A+ in the fun department with a live band, yard games, and a food truck. However, it isn’t a place that I would recommend for a wine tasting. Fat Ass Ranch & Winery specializes in (VERY) sweet wines and is most well know for their Country Peach Wine & Frozen Sangria. Jordan and I tasted their Blackberry, Granny’s Apple Pie, Watermelon, Strawberry Fields, and Country Peach wine then we each got ourselves a swirled Peach & Red Wine Frozen Sangria to enjoy while eating some BBQ & playing horse shoe.

After a full day of wine tasting, Jordan and I were pretty worn out! We stopped by a German restaurant on Main Street called, The Ausländer Restaurant and Biergarten, to grab some dinner to-go. I ordered their pecan-crusted fish of the day that came with a side of vegetables & mashed potatoes. This meal was one of my favorites of the weekend & from what we could tell, the restaurant seemed like a really fun place to sit down, eat, drink, and enjoy live music at.

Sunday-Funday and our first stop was at Java Ranch of course! This morning I ordered an iced hazelnut latte & a bacon, egg, and cheese croissant while Jordan enjoyed another iced white chocolate mocha & a cherry strudel.
We spent the morning time walking around Main Street taking a look at all of the amazing shops & boutiques on the strip. Fredericksburg is a great place to find unique clothing, accessories, boots, home decor, furniture, and more!! We found a shop called, Headquarters Hats, that was filled with an incredible array of western hats, Lucchese boots, and western clothing.
We had the best experience checking out Altstadt Brewery. We spent most of Sunday looking around this awesome brewery, trying their beers, devouring some delicious food, and watching the Texans game (which we wish we didn’t even watch…lol). The architecture of this place is immaculate, the beer is great (my personal favorite was the Amber), the atmosphere was so fun, and the food was scrumptious. I ordered the Altstadt Club & Jordan ordered the Fish & Chips to eat.
Altstadt Brewery also typically offers tours. Unfortunately, the tours were closed at this time due to the pandemic, but I would love to check out the tour next time we visit!
We had dinner reservations at Crossroads Saloon & Steakhouse. This place had a very nice vibe with a live music/dancing section that provided dining & also a fine dining section. We sat in the saloon section to enjoy the music while eating our meal. We both had some drinks (their sangria is great!), split their prime rib special with Brussel sprouts & Mac n’ cheese, and a chocolate cheesecake.
On our way back to the hotel we stumbled upon the Lincoln Street Wine & Cigar Bar that had some great live music playing. We listened to a musician named, Cliff Crawford & his partner on the keys, play some incredible cover songs while we sat by the fire, had some drinks, & shared a cigar before calling it a night.
Monday was Jordan & I’s actual wedding anniversary & we were so excited to spend a relaxing day together enjoying more of what Fredericksburg had to offer.
We started our day with breakfast at Sunset Grill, who is very well known for their eggs Benedict. I ordered The Sunsetter & Jordan ordered The Carlsbad. Both of our eggs Benedict were incredible and oh so filling.
We had plans to hike Enchanted Rock during the day, but unfortunately due to limited availability we weren’t able to book a spot. Next time, we will definitely try to hike again, but I highly recommend booking ahead of time if that’s something you want to do.
Instead of hiking, we walked all around Main Street checking out more & more shops, historic buildings, and the Fredericksburg Brewing Co. It was very fun being able to explore the town some more!
We went to Navajo Grill for our anniversary dinner. We both ordered some awesome drinks & appetizers to start with. Jordan enjoyed their Peach Tea, I ordered the Sangria, and we split the Buffalo Wings. We had full intentions of having a steak together, but the wings were so darn good that we ordered a second basket & their Navajo Fries to have instead.
Navajo Grill was a great spot for a romantic dinner. They sat us outside on their covered patio under twinkle lights & next to their waterfall. They are also a spot that typically has live music on the weekends.
We ended our night listening to our favorite love songs under the stars while we soaked in the hotel hot tub & enjoyed the complimentary champagne they gave us. It was the perfect way to end our first anniversary and an amazing trip.

It was bittersweet waking up Tuesday morning know that our trip had come to an end, but we truly had the greatest time and will definitely be back to visit again. We also couldn’t leave town without one more coffee from Java Ranch!
I hope that each of you enjoyed today’s travel guide/recap of Fredericksburg, TX. Don’t forget to save or share this post if you ever need ideas for when you get to make the trip out there. Have a wonderful weekend & Thanksgiving y’all! I’ll be back to write again very soon.
XOXO, Paige.