On the evening of November 6, the doors of the Spicewood Vineyards Event Center at 1419 County Road 409 open at 6:30, and the music starts an hour later. The man on stage that night will have been formally inducted into the Country Music Hall of Fame 19 days before, and he arrives fresh from Nashville. The room has 70 reserved seats.
That date sums up Spicewood's fall. Between now and December, the best evenings out on this stretch of Highway 71 are held in the community's own wineries, event centers and a new entertainment complex. Several of them would be hard to get into at the same price in a larger city.
A Hall of Fame songwriter, 19 days after Nashville
The Country Music Association named Paul Overstreet to the Hall of Fame's class of 2026 on March 20, in the songwriter category, alongside the Stanley Brothers and Tim McGraw. The Country Music Hall of Fame has set the Medallion Ceremony, where new members are formally inducted, for Sunday, October 18, 2026.
Even if his name doesn't ring a bell, his songs will. Overstreet's catalog includes "Forever and Ever, Amen," "On the Other Hand," "When You Say Nothing at All," "Love Can Build a Bridge," "She Thinks My Tractor's Sexy" and "Some Beach." For the Spicewood show he is bringing Mike Loudermilk and John Patti, and the evening is billed as songs and the stories behind them.
The event listing at Spicewood Vineyards shows how small the room is:
| Ticket | Price | Availability |
|---|---|---|
| General admission | $85 | Not capped in the listing |
| Reserved seating | $125 | 70 seats |
| Artist reception with Paul Overstreet | $50 add-on | 20 spots, performance ticket required |
Reception guests arrive at 5:30, with the reception itself running from 6:00 to 6:30. Twenty people will spend half an hour with a songwriter who, a few weeks earlier, received country music's highest honor.
The season that keeps the stage local
The Overstreet show is a fundraiser and the opening night of Spicewood Live, the six-show season from Spicewood Arts. Each show is a different genre, played in a small Spicewood-area venue. The group started in 2000 to give Spicewood residents ways to see, enjoy and support the visual, performing and literary arts. Money from its annual gala pays for arts scholarships for high school students in Lake Travis and Marble Falls.
The 2026–27 lineup, as listed on the Spicewood Live season page:
| Date | Performer | Venue |
|---|---|---|
| Friday, Nov. 6, 2026 | Paul Overstreet & Friends | Spicewood Vineyards Event Center |
| Friday, Dec. 4, 2026 | Matt Wilson Band | Spicewood Vineyards Event Center |
| Saturday, Feb. 6, 2027 | Will Taylor & Strings Attached | Lopez Hill's Art & Tequila Gallery |
| Saturday, Mar. 6, 2027 | The Peterson Brothers | Iron Wolf Ranch & Distillery |
| Saturday, Apr. 17, 2027 | Two Tons of Steel | Spicewood Vineyards Event Center |
| Friday, May 7, 2027 | A Toast to Tony Campise | Spicewood Vineyards Event Center |
Four of the six nights are at the vineyard. The other two go to Lopez Hill's Art & Tequila Gallery and Iron Wolf Ranch & Distillery, so the season stays in Spicewood the whole way through. The December show is the easiest one to get into. For Matt Wilson Band, doors open at 6:00, the music starts at 7:00, and general admission is $60.
The tasting room calendar holds the weeks between
Between the two concerts, the wineries keep a steady schedule. October is Texas Wine Month, and the Texas Hill Country Wineries Texas Wine Month Passport runs October 1 through 31, 2026. It covers more than 45 Hill Country wineries with free tastings and discounts, and Spicewood Vineyards is on the list. As of today, October 12, that leaves 19 days to use it.
These are the dated events on Spicewood's own wine calendar from now through November:
- October 31, 12:30 to 3:30 p.m. The free Fall Festival at Spicewood Vineyards has live music, kids' crafts and games, food for purchase, wine tasting, and maybe a Halloween-candy pairing.
- November 19, 6:00 p.m. Stone House Vineyard, at 24350 Haynie Flat Road, holds a master class on wines from Australia's Barossa and Eden Valleys for $50 a person.
- November 22, noon to 5:00 p.m. The Fall Wine Club Pick Up Party at Spicewood Vineyards previews three new wines, with live music and light bites. Guests are split into two sessions, and RSVPs had not opened when the listing was posted.
The wine at these events has a strong record right now. The 2022 Las Montañas from Spicewood Vineyards scored 95 points and won a Gold Medal at the 2026 Decanter World Wine Awards. Wine Industry Advisor reported in June that it was one of four Texas wines to win gold. The concert room and the award-winning cellar belong to the same winery, on the same county road.
Weeknights belong to 22111 Hwy 71
For ordinary weeknights, the calendar moves out to the highway. Highway 71 Brewing Co. opened September 6, 2025, at 22111 Hwy. 71, Building 601. Community Impact reported that it is owned by two couples, Kevin and Staci Caputo and Les and Shannon Butler. It pours its own Hill Country beer, mocktails and nitro cold brew, and it has climate-controlled pickleball courts and indoor golf simulators. Hours are noon to 9:00 p.m. Sunday through Thursday and noon to 10:00 p.m. on Fridays and Saturdays.
The brewery's October calendar runs almost every week through the start of November:
- October 16. Live music from Brian Lee
- October 17. Trunk or Treat
- October 23. Live music from Dakota Spellman
- October 24. Spirits High Comedy
- October 31. Halloween at the 71
- November 1. Pickleball tournament
- November 6. Live music from Josh Field
Two nights stand out. On October 31, the Spicewood Vineyards festival winds down at 3:30, so families can go from the vineyard's afternoon to the brewery's Halloween evening without leaving Spicewood. On November 6, Josh Field plays the brewery the same night Overstreet plays the vineyard, so the community has two stages going at once.
The complex is also growing. Community Impact's October 9 roundup of local business news lists an October 12 opening for Infinite Hitting in Building 701 at the same 22111 Hwy. 71 address. It offers batting cages, pitching machines, coaching, camps and clinics. The address that started with one brewery a little over a year ago now has a youth training facility next door.
Booking notes from now through February
A few details on these listings are worth checking before you make plans:
- Overstreet seats are the tightest. Reserved seating stops at 70 and the reception at 20. The winery's listing sends ticket buyers to Spicewood Arts.
- The Passport has a hard end date. It runs out October 31.
- Wine club RSVPs come later. The November 22 pickup uses two sessions, and RSVPs weren't open yet when the listing went up.
- Brewery calendars change. Highway 71 Brewing's schedule is a live page, so confirm a band or event before you drive over.
- Plan ahead for winter. After Matt Wilson Band on December 4, Spicewood Live takes a break until February 6 at Lopez Hill's Art & Tequila Gallery.
If your fall plans center on Spicewood's winery evenings and Hwy 71 weeknights and you'd like to compare notes on the community around them, Bessie Ostertag is always glad to talk Hill Country over a glass of something local. Let's Connect.
