Sipping & Playing in Jacksonville – December 2025 / January 2026

AS WHIT MENTIONED in last month’s Review, there is something truly special about our little town, and sometimes it takes seeing it through someone else’s eyes to be reminded of just how charming it really is. I recently had three friends fly in from different places for a quick visit and watching them light up as we wandered around Jacksonville made me fall in love with it all over again. In just 36 hours, we packed in plenty of good food, laughter, and local love.

Lodging—We booked the Kubli Haus for our stay, and I cannot recommend it enough. It was my first time checking it out, and let me tell you, it is absolutely gorgeous inside. Kathleen, one of the owners, might be one of the kindest hosts you will ever meet. The rooms are beautifully done and fully stocked with coffee, wine glasses, plates, and more. We booked rooms 3 and 4 for the four of us, which meant we had the entire upstairs to ourselves, perfect for late night chats and morning coffee in our pajamas. You truly cannot beat the downtown Jacksonville location.

Shopping—Our day started with a little retail therapy at Volamos Boutique downtown. If you have not been, it is a must stop. The styles are on trend, and the prices are approachable. The staff is warm and helpful, and we all left with something we loved.

Wine Trolley—Next up was the Jacksonville Wine Trolley, and what a fun way to spend the afternoon. The driver was friendly, the ride smooth, and it is such a great way to experience the variety of local wineries without worrying about driving. We started at Rellik for a tasty lunch, then made our way to Hummingbird Estate. Even in the rain, the views were stunning, and we spotted a rainbow across the valley. While we experienced the last wine trolley ride for the season, they offer many other fun trolley options throughout the winter, like the Trolley Lights Tour, so you can still support Jacksonville until the Wine Trolley returns in May.

Great Local Bar—On our walk back from the trolley to Kubli Haus, we noticed a sign for Table Rock City Taphouse and Spirits, which was new to me. It is in the space where Jackass Freight used to be, and curiosity won us over. Inside we found the perfect welcoming local bar. The husband and wife owners were kind, easy to talk to, and clearly care about creating a friendly spot for the community. I will be coming back to watch games or just to relax in a comfortable place. If you have not been, please stop in and support them.

Dinner—We wrapped up the evening with a truly delicious dinner at Gogi’s, just a short walk from Kubli Haus. From the homemade pesto and bread to the soup and entrees, everything was exceptional. Each of us tried a different cocktail and every one was a hit. Gogi’s is on the higher end, and it is worth every penny for the quality, creativity, and service.

In the end, my friends fell completely in love with our friendly, picturesque town, just as I knew they would. Jacksonville has a way of making people feel at home, even on their first visit. As we head into the holiday and winter season, please support our local businesses as you can.
It means the world to them.

Disclaimer: I’m just a wine-loving mom with no formal wine education. Just a mission to find the best places to sip, stay, and savor in Southern Oregon.