The Christmas Wine Affair passport ends Friday, December 18. On Saturday afternoon the Stonewall Chamber of Commerce hosts its toy drive wrapping party on Peach Street, and on Sunday evening LBJ State Park lights its tree for the 57th time. Those three days show how the 2026 season is set up. US 290 carries two holiday calendars, and they barely overlap.
The first calendar belongs to the wine trail. It runs on ticketed passports and multi-course dinners, mostly during daylight hours, and it runs for weeks at a stretch. The second belongs to the town. It runs on single evenings at a short list of community buildings and is mostly free. It saves its biggest weekend for the moment the visitor calendar shuts down. Living a few minutes off 290 means you can use both. The trick is knowing which clock is running on which night.
The Wine Trail Sells Its Season by the Passport
Texas Hill Country Wineries' Texas Wine Month Passport runs through October 31, with tastings and discounts at more than 45 Hill Country wineries. When this post goes up, about ten days are left on it.
The bigger holiday product comes next. The Christmas Wine Affair Passport 2026 runs November 23 through December 18 across more than 50 participating wineries. A $65 individual pass or $100 couples pass gets one complimentary tasting at each participating winery, plus 10% off purchases of three or more bottles there. The ticket is built for the 25-day stretch, so you can use it on a single day or spread it over the whole event.
For anyone who lives here, that 10% on three bottles is a holiday-shopping tool as much as a tasting ticket. The window closes a week before Christmas, the same weekend the town's own calendar fills up.
The Dinners Cluster Into a Few Specific Nights
The wine trail's sit-down events stack onto a handful of dates.
- Tuesday, November 3: Acquired Taste Wines hosts a ticketed four-course Campaign Wines dinner prepared by Trosko Culinary, 6 to 9 p.m.
- Saturday, November 14: two dinners start at 5 p.m. One is the Fall Dinner Party at Hilmy Cellars at 12346 East U.S. 290. The other is the ticketed five-course Wild Game Estate Dinner at Meierstone Vineyards at 573 Meier-Stone Road.
- Tuesday, December 8: Texas Hill Country Wineries holds its Holiday Winemaker Dinner at Hill + Vine in Fredericksburg. It features six member wineries and benefits the association's Wine Industry Scholarship Fund.
The November 3 dinner is the first holiday season for the trail's newest tasting room. Acquired Taste Wines opened June 6, 2026, according to a press release published by WineBusiness. It is a multi-brand concept founded by Dave Bryant and built as a portfolio of separate wine labels rather than a single estate. The tasting room is at 239 Miracle Mile, Ste. O. Another project is further out. The Fredericksburg Standard reports that THE DEBATE has construction underway on a Stonewall tasting room and hospitality venue, with opening expected in spring 2027.
Just east, in Johnson City, Texas Hills Vineyard at 878 RR 2766 has two free Friday Night Frights screenings left, October 23 and 30 at 6:30 p.m., with food and drink for sale. Its Halloween in the Hills on October 31 runs 7 to 10 p.m. Tickets are $65 individual or $100 for two and include wine, appetizers and entertainment.
The Town's Calendar Starts After Dark and Stays Small
The community side is quieter, and its hours are different. Most of the listings on the Stonewall Chamber of Commerce calendar that give a start time begin at 5:30 or 6:30 p.m., after the tasting rooms have done most of their day's business.
| Date | Event | Time and place |
|---|---|---|
| Fri., Oct. 30 | Trunk or Treat at Rheingold School | 5:30 to 7:30 p.m. |
| Sat., Nov. 7 | Pleasant Hill Rocky Community Club 77th Annual Smorgasbord | Check with the club for time |
| Fri., Nov. 13 | Stonewall Chamber Bingo Night | 6:30 p.m., Chamber building, 250 Peach Street |
| Wed., Dec. 9 | Stonewall Christmas Parade | Begins 6:30 p.m. |
| Fri., Dec. 11 | Chamber Christmas Yard Decorating Contest | Rules on the Chamber poster |
| Sat., Dec. 19 | Chamber Toy Drive Wrapping Party | 1 p.m., Chamber building, 250 Peach Street |
| Sun., Dec. 20 | 57th Annual Tree Lighting, LBJ State Park | 5:30 to 7:30 p.m. |
Two dates on that table need a closer look.
The Stonewall Christmas Parade falls on a Wednesday, December 9, at 6:30 p.m. The Chamber listing doesn't post a route, so confirm where to stand with the Chamber before you head out. It lands the night after the Holiday Winemaker Dinner and in the middle of the Christmas Wine Affair, but on a weeknight, so it doesn't compete with the trail's Saturday traffic.
The Christmas Yard Decorating Contest is listed for December 11. Deadlines and instructions are on the Chamber's poster, so anyone planning to enter should get the rules from the Chamber directly.
The smorgasbord just over the line
The Pleasant Hill Rocky Community Club's 77th Annual Smorgasbord is on the Stonewall Chamber calendar for Saturday, November 7. The listing gives the date and the 77th year and nothing more. Its home is the Pleasant Hill Rocky schoolhouse out toward Hye, across the county line from Stonewall proper. Back in 2014, the Austin American-Statesman described the building as a two-room schoolhouse from 1927 that had served as a community center since the 1950s. The paper called the smorgasbord a November potluck fundraiser that had raised more than $50,000 over the previous 12 years for groups including the Johnson City VFD, North Blanco EMS and the Johnson City Library. That account is more than a decade old. Check with the club for this year's start time, location and menu.
The Handoff Weekend, December 18 to 20
This is where the two calendars meet. The Christmas Wine Affair's final day is Friday, December 18. The town's two most community-minded events follow on the next two days.
Saturday, December 19, 1 p.m. The Chamber's Toy Drive Wrapping Party takes over the Chamber building at 250 Peach Street. The 2026 listing doesn't say how many families the drive expects to serve. Last year's notice from St. Francis Xavier Catholic Church said the gifts were for children and families in the Stonewall community and that the Chamber planned to help 100 area families. An earlier Chamber letter from 2022 reported 95 meal packs and toy bundles handed out that year, with cash and check donations going to food, toys and clothing.
Sunday, December 20, 5:30 to 7:30 p.m. The 57th Annual Tree Lighting at Lyndon B. Johnson State Park & Historic Site carries on a tradition President and Mrs. Johnson started. Festivities begin at the Visitor Center with carolers, a live nativity, Santa and refreshments. After dark, the Sauer-Beckmann Farm offers a lamp-lit tour, decorated for Weihnachten and serving traditional German Christmas cookies. One scheduling detail matters if you want daytime time at the farm. It closes at noon that day and reopens after the ceremony. The park is also collecting canned goods and nonperishable items for the Fredericksburg Food Pantry, so the trip doubles as a donation run. For the rest of the park's seasonal schedule, our earlier piece on how the LBJ Ranch visit now runs on the state park's calendar covers the daytime side.
The Family Weekends on 290
Texas Wine Country Jellystone Park at 10618 East U.S. 290 runs its own themed weekends alongside both calendars. November covers four weekends between November 6 and 29, including Carni-FALL and Thankful and Twinkling. The December lineup runs from December 4 into January 3, 2027, with weekends such as Winter Wonderland, Santa's Workshop and Bear-y Merry Christmas. For households with kids or visiting grandkids, these weekends fill the Saturdays the town calendar leaves open.
If your year in Stonewall runs from peach stands to tree lights, our piece on the best week for Stonewall peaches covers the summer end. The Stonewall neighborhood page has more on the community between the two.
Anna and Brittney at Wynne-Smith Horton Real Estate Group keep track of Stonewall's calendar the way neighbors do, from the Chamber's bingo nights to the tree lighting at LBJ State Park. If you're hosting family along 290 this December and want a local suggestion for a quiet evening, or have questions about owning a home near the wine trail, we're happy to talk. Contact Us.
