Every San Antonio benefits deadline that matters, on one page — enrollment windows, closing dates, giveaways, and the programs open right now. Every entry is checked against its source (each one links to it), and this page is updated as months roll. Last updated: October 21, 2026.
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Open right now
Head Start preschool applications — open now, no closing date announced
City of San Antonio Head Start (children who are 3 or 4 by September 1, 2026). Apply at SAHeadStart.org or call 210-206-5500. Our guide
Source: City of San Antonio Head Start · Verified Oct 21, 2026
Child Care Scholarships (CCS) — waitlist open now
Workforce Solutions Alamo’s waitlist is in effect and the average wait is 18–24 months — your place in line starts the day you apply. Our step-by-step guide
Source: Workforce Solutions Alamo · Verified Oct 21, 2026
Medicare open enrollment — open now through Monday, December 7
The yearly window to join, drop, or switch a Medicare Advantage or Part D drug plan for 2027. Details under December, below.
Source: Medicare.gov · Verified Oct 21, 2026
November 2026
Sunday, November 1 — Health insurance open enrollment OPENS
Open enrollment for 2027 Marketplace coverage opens at HealthCare.gov and runs through January 15. Two Texas plans (Cigna and Baylor Scott & White individual plans) are leaving after December 31, 2026 — their members must pick a new plan. Our full guide
Source: HealthCare.gov · Verified Oct 21, 2026
November 1–30 — Food4SA, the Food Bank’s November food drive
A month-long food drive — a way to give, not a distribution. If you need food this month, the Food Bank’s own help runs as always: 5200 Historic Old Hwy 90, walk-in Monday–Friday 8 AM–5 PM, 210-337-3663.
Source: San Antonio Food Bank · Verified Oct 21, 2026
Saturday, November 7 — U.S. Veterans Day Parade, noon
Starts at Milam Park and runs along Houston Street in downtown San Antonio. Free public event.
Source: City of San Antonio · Verified Oct 21, 2026
Saturday, November 21, 9–11 AM — Free turkey giveaway, New Life Christian Center
6610 US Hwy 90 W. A free turkey for your family, no registration — arrive early. Announced by the organizer, Zulma Jimenez (210-279-1357); church line 210-679-6050.
Source: Organizer’s announcement, covered by San Antonio Free Meals · Verified Oct 21, 2026
December 2026
Monday, December 7 — Medicare open enrollment CLOSES
Last day to join, drop, or switch a Medicare Advantage or Part D drug plan for 2027. Changes take effect January 1, 2027. Compare plans at Medicare.gov Plan Compare or call 1-800-MEDICARE (1-800-633-4227).
Source: Medicare.gov · Verified Oct 21, 2026
Tuesday, December 15 — Enroll by today for Marketplace coverage starting January 1
Enroll by December 15 and your 2027 coverage starts January 1. Enroll after (up to January 15) and coverage starts February 1. Local free help: EnrollSA, (210) 977-7997. Our full guide
Source: HealthCare.gov · Verified Oct 21, 2026
Looking ahead
Friday, January 15, 2027 — Health insurance open enrollment CLOSES
The last day to enroll in a 2027 Marketplace plan (coverage starts February 1). After this date, enrollment takes a qualifying life event.
Source: HealthCare.gov · Verified Oct 21, 2026
January 2027 — VITA free tax preparation sites open
Free tax help runs January through April each year. Sites and hours are announced as the season opens — check our program status board.
Source: San Antonio Benefits program status board · Verified Oct 21, 2026
Not sure what fits your family?
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San Antonio Benefits is a free community guide, not a government agency. Dates come from the sources linked on each entry and can change — the source always has the final word.
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