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Women’s Wine & Chocolate Walk 2024

May 18 @ 12:00 pm - 6:00 pm

$30 – $750

Grab your friends for an afternoon filled with wine, chocolate, shopping, food, and entertainment in historic downtown Middletown. The Women’s Wine & Chocolate Walk is an event just for ladies 21+, hosted by Downtown Middletown Inc. Although walking is involved…we can’t promise you will burn more calories than you consume!

Make sure to follow our Facebook Page and Event Page for updates, and read below for more details.

How it works: At check-in, you will trade your ticket for a wine tasting glass, swag bag, and tasting map. You can also check out our raffle baskets and get a free raffle ticket for donating a canned good item. Then you’re off! Your map will guide you to 10 wine stops and 10 chocolate stops throughout downtown Middletown. Along the way, enjoy amazing shopping, restaurants, and entertainment.

Ticket Sales: Regular ticket sales will open later in the month. Remember to purchase early because quantities are limited.

SuperStar VIP Package: NEW! Introducing the hottest ticket in town, with only 3 of these packages available, you’ll want to book early. This package includes 5 VIP tickets with a pre-party mimosa brunch, a special swag bag for each of you, 10 raffle tickets, 5 bottles of wine, front of the VIP line access, and a 1-hour chauffeured golf cart so that you can visit the farthest stops without any blisters!

VIP Tickets: Want to arrive early to avoid the crowd at check-in? How about a welcome reception with appetizers and nibbles? Best of all, do you want an extra wine and chocolate stop? If so, the VIP ticket is for you! We have a limited number of these available, so book early.

General Admission Tickets: This is a great value for 10 wine tastings and 10 chocolate samples, plus entertainment, shopping, and restaurants ready to serve you.

Event Shirts: Purchase your shirts while buying your tickets. Just scroll down beyond the ticket options to choose your size. Shirts will be available for pick up in May.

Check-in: Meet us at the Windamere, 2 S. Main Street in downtown Middletown. You will select a specific check-in time when you book. Donate a personal hygiene item, cleaning supplies, or non perishable food and get a free raffle ticket at check-in! Donate as much as you’d like, but there is a limit of 1 free raffle ticket per person. All donations will benefit St Vincent de Paul.

What to Wear: Rock out to this year’s theme, Popstars Through the Eras. Wear your favorite concert tee or go all out and dress head-to-toe like your favorite pop sensation. Whether you swiftly represent an era, you are living like a material girl, or you’re destined to be a Grammy-winning child, we can’t wait to see your popstar threads. Remember to wear comfortable shoes because there is a bit of walking involved.

Shuttle: This is definitely not a fitness event. There is plenty of time for a leisurely pace. If you want a little more wine and chocolate and a little less walk, there will be a shuttle available to drop you off near the farthest stops.

Why should you participate? This event supports dozens of small businesses and serves as a fundraiser for Downtown Middletown Inc. You’ll get an exciting afternoon with your gal pals, and you’ll be supporting a great cause at the same time!

Questions? For general questions, vendor information, or sponsorship opportunities, please contact [email protected]


May 18
12:00 pm - 6:00 pm
$30 – $750
Event Categories:


Downtown Middletown
Middletown, OH United States + Google Map
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