Pour Trail
Upcoming · Saturday, May 2, 2026

4th ANNUAL KENTUCKY DERBY WATCH & WINE ROOFTOP FUNDRAISER

4th ANNUAL KENTUCKY DERBY WATCH & WINE ROOFTOP FUNDRAISER in Henrico, VA — charity event benefiting Wounded Warrior Project. May 2, 2026. From $55.

Best for couples Best for groups food wine 21+ only
Saturday, May 2, 2026
$55
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Quick facts

At a glance.

Dates
Saturday, May 2, 2026
Duration
Single day
Best for
Couples, Groups
Atmosphere
Casual
Food
Bring or buy nearby
Age
21+ only

The story

About this festival.

4th ANNUAL KENTUCKY DERBY WATCH & WINE ROOFTOP FUNDRAISER is a charity food and wine event held annually on May 2, 2026, in Henrico, Virginia — a rooftop watch party benefiting the Wounded Warrior Project with a fundraising goal of $1,500. The event runs from 5:30 PM to 8:30 PM at the Luxury Rooftop Patio at 3500 Cox Rd, organized by Ladies of Short Pump, a local community group. General admission early bird tickets are priced at $55, with group and sponsorship tiers reaching up to $600.

4th ANNUAL KENTUCKY DERBY WATCH & WINE ROOFTOP FUNDRAISER centers on watching the Kentucky Derby live on large TV screens while guests enjoy wine, a buffet, and faux betting. Each standard ticket includes 2 drink tickets, patio seating, and 2 raffle tickets. The event encourages Derby dress — big hats, bow ties, and dancing shoes — and features a silent auction, chance drawings with prizes ranging from $15 to $40, and a program guide with local business advertising. Chef Mark Burns is on site, and the event has a live entertainment component with music.

For those seeking a more elevated experience, table packages seat groups of 4, 6, or 10 and include perks such as program guide advertising, speaking opportunities, and a 90- to 120-minute vintage car ride arranged through RB Vintage Car Service. Tables of 4 are priced at $200, tables of 6 at $240, and tables of 10 at $600. Wounded warriors and veterans can contact ladiesofshortpump@gmail.com or call 804.310.6895 for a discounted access code, valid through April 20, 2026. Early bird pricing closes April 20.

Getting there

Location & logistics.

What to expect

The experience.

What you'll pour

A mix of varietals from regional producers. Start light, work toward the bigger reds.

The setting

Held at www.3500wv.com Luxury Rooftop Patio in Henrico. Check the venue page for layout details.

The crowd

A mix of regulars and newcomers. Knowledgeable pourers happy to walk you through what you're tasting.

Worth the trip

Arrive early, hit your must-try wineries first, then wander. That's the move.

Reviews

What people are saying.

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Frequently asked

Common questions.

When is the next 4th ANNUAL KENTUCKY DERBY WATCH & WINE ROOFTOP FUNDRAISER?
4th ANNUAL KENTUCKY DERBY WATCH & WINE ROOFTOP FUNDRAISER is held Saturday, May 2, 2026 at www.3500wv.com Luxury Rooftop Patio, Virginia. Confirm the exact date with the organizer before booking travel.
How much do tickets cost?
$55. Prices typically rise closer to the event — early bird often saves $15–30.
Is parking available at 4th ANNUAL KENTUCKY DERBY WATCH & WINE ROOFTOP FUNDRAISER?
Parking details are set by the organizer closer to the event. For lakeside and park venues like this one, on-site spots fill early — plan to arrive 30 minutes before doors, carpool, or take a rideshare.
Is 4th ANNUAL KENTUCKY DERBY WATCH & WINE ROOFTOP FUNDRAISER family-friendly?
No — 4th ANNUAL KENTUCKY DERBY WATCH & WINE ROOFTOP FUNDRAISER is a 21+ event. You'll need a valid ID at entry. Some festivals offer designated driver (DD) tickets at a reduced price for non-drinking adults.
Can I buy tickets at the door?
Sometimes — but wine festivals frequently sell out in advance, especially events with under limited capacity. Buying ahead online almost always saves money and guarantees entry.
Who is 4th ANNUAL KENTUCKY DERBY WATCH & WINE ROOFTOP FUNDRAISER best for?
This festival is a great fit for couples, groups, foodies.

More Virginia

Other festivals nearby.

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