The 14th annual culinary fundraiser runs Tapas & ’Tinis Nov. 5 and the main meadow fest Nov. 7 — 30+ restaurants, serious pour lists, 21+, and a price tag that deserves honesty.
Quick Facts
- When: Thu Nov 5, 2026 (Tapas & ’Tinis, 7–10 p.m.) · Sat Nov 7, 2026 (main festival)
- Where: West Meadow, 300 N New York Ave, Winter Park
- Who: 21+ only · rain or shine · country-western dress code energy
- Tickets: Official portal at cowsncabs.com/tickets — Tapas listed ~$275; Saturday from ~$225 (GA / VIP / Ultimate VIP) per Sep 2026 press
- Cause: Children’s charities (2025: $1,088,000; lifetime $4.1M+)
Not a polite meadow night
Winter Park’s West Meadow does a lot of polite community things. Cows ’n Cabs is not one of them — not politely, anyway.
The 14th annual food, wine, and music fundraiser — presented by HostDime — returns to 300 N New York Ave for two nights: Thursday, Nov. 5, and Saturday, Nov. 7, 2026. Official site copy is blunt about the scale: Saturday brings 30+ restaurants, 60+ beverage vendors, and live music across the fenced meadow. Thursday is the smaller sibling.
Thursday tent, Saturday walkaround
Tapas & ’Tinis (Nov. 5) is capped at 300 guests, runs 7–10 p.m. under the tent, and pairs small plates with martinis and live music. It’s the “you might actually talk to a chef” night. Saturday’s main event is the gluttonous walkaround the name promises — VIP gates earlier, general admission later into the evening (press has listed VIP from 6 p.m. and GA 7–10:30 p.m.; check the ticket portal for the exact times before you lock a calendar invite).
The sticker is the story
About that price: local press covering the ticket drop lists Tapas & ’Tinis at $275 and Saturday tickets starting at $225, with VIP and Ultimate VIP above that. Those numbers come from September coverage of the on-sale, not a static HTML price list on the homepage — so treat the SquadUp checkout on cowsncabs.com/tickets as the live source of truth. Either way, this is not a $60 tasting night. It’s a charity flex with all-inclusive food and drinks baked into the ticket, and OCH is not going to soft-pedal the sticker.
Who’s cooking — and who gets the check
What’s on the plate? Press citing the organizers’ release names early 2026 restaurant partners including Omo by Jont, Chapman, Salt and Cellar, Morimoto, Primo, and The Reverie, with more expected. That’s a Winter Park / Orlando chef roll call compressed into one meadow — the reason people who can afford it buy early. The event sells out most years; non-refundable tickets; emailed to the purchaser.
The mission is the other half of the story. Organizers say 2025 raised $1,088,000, pushing lifetime impact past $4.1 million for Central Florida kids and families. The About page notes leadership now with Tina Larue and Liz McGlamery, and proceeds split toward groups such as 4Roots, After-School All-Stars, and Winter Park Day Nursery. Boots and hats are encouraged. The park is grass. Pets stay home. Valet is complementary at the post office lot; rideshare is what the FAQ actually recommends.
If you’re shopping for a cheaper Winter Park sip-and-sample, this isn’t it — and that’s fine. Cows ’n Cabs is the once-a-year meadow dinner where the ticket is the donation and the night is the thank-you note.
Why We’re Hyped
- Chef density you can’t assemble yourself— a deep slate of high-demand Orlando/Winter Park kitchens in one fenced park.
- Two formats, one weekend— 300-person Thursday intimacy vs. Saturday’s full meadow walkaround.
- Receipts on the charity claim— seven-figure 2025 raise, not vague “benefits local nonprofits” fog.
- Clear logistics— official FAQ covers 21+, rain-or-shine, dress, parking/valet, refunds.
The Details
- Tapas & ’Tinis: Thursday, Nov. 5, 2026 · 7–10 p.m. · 300 guests
- Main festival: Saturday, Nov. 7, 2026 · West Meadow (VIP earlier / GA evening — see ticket page for exact times)
- Where: Winter Park’s West Meadow · 300 N New York Ave, Winter Park, FL 32789
- Age: 21+
- Tickets: cowsncabs.com/tickets
- Info: cowsncabs.com
