On Saturday, Nov. 14, the City of Alamo Heights will hold its first chili cook-off at Kellyanne Park and the Heights Pool parking lot, 250 Viesca. It runs from 11 a.m. to 6 p.m., and the city charges nothing to compete or to attend. The event comes in the same year the Alamo Heights Rotary Club paused Alamo Heights Night, the Fiesta block party it ran from 1987 through 2025, apart from cancellations in 2020 and 2021.
The two events run on different business models. Alamo Heights Night needed its own revenue to fund the next year. The cook-off is a free city event, held in a park where a public food-and-drink operation already runs every week. That difference explains why the new event looks the way it does, and it also shows what it can and cannot replace.
A Fundraiser That Had to Fund Itself
For almost four decades, Alamo Heights Night was the Rotary Club's spring contribution to Fiesta. The event's own site describes it as a family-friendly outdoor block party with food, drink, entertainment, games and rides, and says it raised more than $2.4 million for charitable purposes.
That money had to come back in every year. The San Antonio Express-News reported in March 2026 that club president Rick Thorp's release blamed declining attendance and revenue. The release said, "Revenues last year did not raise sufficient funds for organizers to finance the event this year. Costs have gone up and attendance was not what it was before COVID." Texas Public Radio also reported several years of lower turnout and financial support after the 2020 and 2021 cancellations.
The official site still says the 2026 event is paused and has not been rescheduled. It also says any future dates will be posted there. In September, MySA asked the Rotary Club whether the event would return in 2027 and did not immediately get an answer. For now, nothing has been announced for April.
A charity event that has to cover its own costs before it can give anything away gets squeezed when costs go up and crowds shrink. The cook-off avoids that problem by design.
What the City Built Instead
The city's announcement, posted Oct. 15, says the City of Alamo Heights wants "to start something new to bring the community together and have some fun." It is organizing the event together with the Heights Pool. The event has no gate, no ticket and no fundraising target. The city lists these features:
- A chili competition with cash prizes and 22 contestant spots
- A cornhole tournament, also with cash prizes
- Free chili samples from the contestants
- Bounce houses, face painting and balloon artists for kids
- College football streaming in the park, including UT vs. LSU and A&M vs. Tennessee, both played that day
- Food and beverage service from POOLSIDE throughout the park
According to the city, cooks will compete for cash prizes and for "the bragging rights of having the best chili—at least on this side of the San Antonio River."
The cooks are the only limited part of the day. The 22 spots go to the first 22 people who sign up, and registration runs through Heights Pool staff by email at [email protected]. This post publishes about three weeks before the event, so anyone planning to bring a pot should email sooner rather than later.
Why Kellyanne Park Already Works for This
The venue matters as much as the format. Heights Pool is an outdoor membership swim club at 250 Viesca St. It has a large pool, a diving well, a kiddie pool, courts, and POOLSIDE, its grill and full bar. The pool's history goes back to when it was city-run. In January 2025, the City Council approved lease terms with Clayton and Stacy Smaistrla of Alamo Heights Pool, LLC, and authorized city officials to negotiate and execute the lease.
The part that matters for the cook-off is next door. POOLSIDE (in the Park) at Kellyanne Park is open to everyone, and no pool membership is needed. The weekly schedule at the pool already runs on a steady rhythm:
| Day | What's on at Heights Pool |
|---|---|
| Tuesday to Thursday | POOLSIDE happy hour, 3 to 7 p.m. |
| Thursday | Pasta night at the grill, then league pickleball 5:30 to 8:30 p.m. |
| Friday | Fajitas and ritas |
| Saturday | College football on every TV |
That last row is where the cook-off comes from. On Nov. 14, the city takes a college football Saturday the pool already hosts, opens it up to the whole park, and adds chili, cornhole and two bands. The park also has the October specials running now: free ice cream on Tuesdays from 5 p.m. while it lasts, kids eat free with an adult entrée on Wednesdays, and a Thursday movie night on the lawn. Those specials are listed for October, so check the pool's hours and events page for what carries into November.
The pool is in its 2026 off season, which runs Sept. 8 through Dec. 13. In November, it is open Wednesday and Thursday from 3 to 8:30 p.m. and Friday through Sunday from noon to 9 p.m. Nov. 14 falls on one of its full-day Saturdays.
How Nov. 14 Lays Out
The music schedule splits the afternoon into two parts. Texas Tide opens from noon to 4 p.m., and The Texases play the main set from 4 to 6 p.m. Alamo Quarry Market has its WinterFest the same evening from 5 to 7 p.m. at 255 E. Basse Road. Family Service's calendar lists WinterFest under November 2026, so the date matches this year's cook-off.
| Time | Kellyanne Park, 250 Viesca | Alamo Quarry Market, 255 E. Basse Rd. |
|---|---|---|
| 11 a.m. | Cook-off opens | |
| Noon to 4 p.m. | Texas Tide | |
| 4 to 6 p.m. | The Texases | |
| 5 to 7 p.m. | WinterFest | |
| 6 p.m. | Cook-off closes |
Because the two events overlap by an hour, households have to choose how to finish the day. One option is to stay for the full set by The Texases and arrive at the Quarry for WinterFest's last hour. Another is to leave the park at 5 for the start of WinterFest. Either way, the day ties the old center of the 09 to its commercial edge on Basse Road.
The next morning, the Alamo Heights Farmers Market sets up near Whole Foods at the Quarry, as it does every Sunday from 10 a.m. to 2 p.m.
The Calendar Around It
Through the rest of the fall, Kellyanne Park stays the steadier of the two places. POOLSIDE in the park runs its weekly schedule until the off season ends Sunday, Dec. 13. On Broadway, the next openings will come over a longer timeline. The Express-News reported that PopUp Bagels planned to begin renovating its first local shop at 7959 Broadway in October and expected the space to be ready by December. Further out, the Express-News reported that Dallas-based Vandelay Cos. plans to open Hudson House next spring and the New Orleans-inspired Jack & Harry's next summer at 5307 Broadway, in the former Nix clinic.
None of those openings arrives in time for Nov. 14. For this fall, the community's shared Saturday is in Kellyanne Park, it is free, and the city calls it the 1st Annual cook-off, which means it intends to hold the event again.
If you are entering a pot of chili or just bringing a chair, I hope to see you at Kellyanne Park on the 14th. Jacob Rocha keeps track of what is changing in Alamo Heights, from new events like this one to the openings coming on Broadway. If you have questions about the neighborhood, you can ask me between chili samples or before then. Let's Connect.
