Hill Country Events: October Through the Holidays 2026
The stretch from October through the New Year is when the Hill Country does its best work, and I went back through the event calendars again this week so this guide reflects what is actually confirmed as of September 24, 2026. It covers ten events across Canyon Lake, Wimberley, New Braunfels, San Marcos, and San Antonio, from the wine trail and the festivals to the parades and light displays that close out the year. Everything here was rechecked against official sources, and each event links out to the organizer so you can confirm details before you head out.
A note on the earlier event guides on this blog: they have been moved to the archive at the bottom of the blog page so the front page stays current. This is the guide to bookmark. As organizers confirm or adjust dates, I will keep this one updated.
Between the winery passport, the Halloween gatherings in Wimberley and at the lake, ten days of Wurstfest, and the holiday lights from San Antonio to EmilyAnn, there is a reason to be out and about almost every weekend. That rhythm is one of the biggest reasons people choose the Hill Country, and it is the rhythm I help clients find every day.
Texas Wine Month Passport
October is Texas Wine Month, and the Hill Country wineries have put together a passport that makes it easy to explore. Buy the pass and you get tastings at more than 50 member wineries from Fredericksburg to Hye and points between, good all month long at your own pace. That is the beauty of it, every stop is a reason to drive a prettier route and learn how far everything really is from everything else. For second-home buyers and visitors scouting the Hill Country, it doubles as the lowest-pressure tour of the region you will ever take.
More DetailsWimberley Market Days
Market Days has been the first-Saturday gathering in Wimberley for decades, and October 3, November 7, and December 5 round out the 2026 dates. Hundreds of vendors set up across Lions Field with live music and food, and the whole town seems to be out walking. If you are relocating or just considering a move, go once and you will understand Wimberley's pull better than any brochure could explain it. It is also the easiest place in the county to run into people and ask what it is really like to live here.
More DetailsGruene Music and Wine Festival
The Gruene Music and Wine Festival marks its 40th year this October, four days of live music and Texas wines spread through the historic district steps from the Guadalupe River. Robert Earl Keen's Then and Now tour opens at Gruene Hall on Thursday night, the Stars and Guitars night with Shane Smith and the Saints lands Friday, and The SteelDrivers play Saturday. It is a compact, walkable festival that shows off the best of New Braunfels in a single weekend, and weekend shows sell out, so I would grab tickets early.
More DetailsDay of the Dead River Parade and Muertos Fest
San Antonio does Dia de los Muertos as well as any city in the country, and it all lands the weekend of October 23. The Day of the Dead River Parade floats decorated barges down the River Walk on Friday night with music and costumed riders, and it is free to watch from the banks. Across town, Muertos Fest at Hemisfair runs the full weekend with altars, music, dance, and food. Both are free, and together they are the clearest picture of what makes San Antonio special. For anyone weighing the San Antonio side of the Hill Country, this is the weekend to see the city at its best.
More DetailsBoo! Hole Halloween
Wimberley turns Blue Hole Regional Park into a family celebration for Boo! Hole Halloween on Saturday, October 24, from 4 to 9. There is a trick-or-treat trail, carnival games, a costume contest, a haunted trail for the brave, and live music, and admission is free. It is the small-town Halloween that families remember for years, and it is a wonderful introduction to Wimberley for anyone thinking about a move with kids or grandkids close by.
More DetailsCanyon Lake Fall Fun and Pumpkin Carving
Back at the lake, the Canyon Lake Chamber hosts Fall Fun and Pumpkin Carving on Monday, October 26, from 4 to 6. It is a simple, neighborly afternoon, pumpkins, carving tools, and an easy evening for families. Gatherings like this are the everyday rhythm of lake living, the kind of thing you only truly find once you are part of the community. For newcomers and second-home owners alike, it is a friendly, low-pressure way to meet people at the lake. Watch the Chamber calendar for exact location and any updates.
More DetailsThe 65th Annual Wurstfest
Wurstfest returns November 6 through 15 for its 65th year, ten days of German-Texan music, food, and carnival rides on the banks of the Comal River. It has started the first Friday of November for as long as anyone can remember, and the town plans its whole fall around it. General admission has been free in recent years, with food, drinks, and some attractions carrying separate fees. For New Braunfels buyers and sellers alike, it is the signature event of the year and the surest sign the holidays have arrived in the Hill Country.
More DetailsTexas Capital Air Show
The Texas Capital Air Show flies into San Marcos Regional Airport on November 7 and 8, with the F-22 Raptor, F-16s, and the Wings and Warriors Jump Team on the schedule. Air shows are a rare treat this far from the big bases, and San Marcos puts on a strong one with static displays and vendors around the flying. It is easy to spend a full day there, and the airport sits right off I-35, an easy drive from Canyon Lake, Wimberley, or New Braunfels.
More DetailsFord Holiday River Parade
San Antonio's 45th annual Ford Holiday River Parade rolls the Friday after Thanksgiving with illuminated barges, live music, and floats along the River Walk, all under the city's holiday lights. It is one of the most photographed nights in Texas, and it is free to watch from the banks if you arrive early. For retirees and families alike it is a classic holiday outing, and it sits an easy drive from every community I serve. I would plan to get there ahead of time, because the best viewing spots go quickly.
More DetailsEmilyAnn Trail of Lights
The EmilyAnn Trail of Lights opens November 28 and runs most nights through December 26, turning acres of the theatre gardens into a walking trail of lights with live music, visits with Santa, and refreshments. Admission is free with a suggested donation that supports the theatre. It is the unhurried, small-town version of Christmas that a lot of people move to Wimberley for, and it is worth the drive from anywhere in the Hill Country, especially on a clear night when the stars show up too.
More DetailsPlanning the Season Across the Hill Country
A few notes from my years around here that might help you plan the season:
- October belongs to the wine trail. The Texas Wine Month Passport covers the whole month at your own pace, and the Gruene Music and Wine Festival on October 8-11 is the concentrated weekend version, with Robert Earl Keen opening at Gruene Hall on Thursday. If you only pick one weekend for wine and music, pick that one.
- Wimberley gives you two good reasons to visit in October. Market Days on the first Saturday, and Boo! Hole Halloween at Blue Hole on the 24th. Together they show both sides of the town, the shopping and gathering side and the outdoors and family side.
- The lake keeps its own calendar. This month it is Fall Fun and Pumpkin Carving on October 26 through the Chamber. Keep the Chamber calendar bookmarked for December too, because the Noon Lions Christmas Parade rolls down FM 2673 in Sattler the second Saturday of December every year, and it is the friendliest parade in the county.
- San Antonio's Day of the Dead weekend is worth planning around. The river parade Friday night and Muertos Fest at Hemisfair all weekend, both free, both within an easy drive of every community I serve. If you are considering San Antonio, go and feel the city during its best weekend of the year.
- Make room for the ten days. Wurstfest runs November 6 through 15 in New Braunfels, its 65th year. With that on the calendar, there is no excuse for a quiet November.
- The holiday season opens the day after Thanksgiving. The Ford Holiday River Parade in San Antonio on November 27 kicks it off, and the EmilyAnn Trail of Lights in Wimberley opens the next evening. You could catch both in one long weekend and still be home for Sunday dinner.
“When the weather turns and the towns fill up with lights and music, I tell people the Hill Country is putting on its best clothes. That is the season when visitors start to feel like neighbors, and it is the reason so many of my clients began as weekend visitors and ended up with a home here.”
Steve Giannone
If you are thinking about a move to any of these communities, pick two events from this list and go. You will learn more about a town in one afternoon than a month of listing pages will teach you. And when you are ready to talk neighborhoods, market values, or what life at the lake is really like in January, I am a phone call away.
Thinking about a move to the Hill Country? Let us talk.