Pour Trail
Sip and Paint With Pumpkins wine festival in Lexington, Kentucky
Upcoming · Friday, October 30, 2026

Sip and Paint With Pumpkins

Join us at KecShelby for a fun-filled fall evening of creativity, wine, and pumpkins!

other21+ only
Friday, October 30, 2026
TBA
Know the ticket link?

Quick facts

At a glance.

Dates
Friday, October 30, 2026
Duration
Single day
Best for
Wine lovers
Atmosphere
Festive
Food
Bring or buy nearby
Age
21+ only

The story

About this festival.

Getting there

Location & logistics.

kecshelby Vineyards and Winery
901 North Yarnallton Pike, Lexington, KY
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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 kecshelby Vineyards and Winery in Lexington. 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 Sip and Paint With Pumpkins?
Sip and Paint With Pumpkins is held Friday, October 30, 2026 at kecshelby Vineyards and Winery, Kentucky. Confirm the exact date with the organizer before booking travel.
How much do tickets cost?
Pricing for the next edition hasn't been announced. Most comparable wine festivals in Kentucky run $40–$95 for general admission. Check the organizer's site for current pricing.
Is parking available at Sip and Paint With Pumpkins?
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 Sip and Paint With Pumpkins family-friendly?
No — Sip and Paint With Pumpkins 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.

More Kentucky

Other festivals nearby.

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