Women’s Wine & Chocolate Walk 2026!

Grab your friends for an afternoon filled with wine, chocolate, shopping, food, and entertainment in historic downtown Middletown.

The Women's Wine and 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!

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. Then you’re off! Your map will guide you to 10 wine stops and 10 chocolate stops throughout downtown Middletown. Along the way, stop to enjoy amazing shopping, restaurants, and entertainment.

SuperStar VIP Package: This is the HOTTEST ticket in town! With only a few 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, and a 1-hour chauffeured golf cart so that you can visit the farthest stops without any blisters! If you have less than 5 people in your group and want to pair up with another group, contact heather@downtownmiddletown.org to ask about availability.

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 treats, 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. A limited number of shirts will be available at the presale on March 7.

Raffle: We have some great raffle baskets for you to win! Just purchase raffle tickets online or when you check in at the event. All proceeds from the raffle will go to Downtown Middletown Inc. If you purchase your raffle tickets online, we will have them filled out and ready for you at check-in. Just visit the raffle table and pick which baskets you would like to enter to win.

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.

What to Wear: Many ladies want to wear an outfit that fits with our event theme. The theme will be announced in March. Some women choose to buy and wear one of our event t-shirts, available at the presale and on Eventbrite. We recommend wearing comfortable shoes because there is a bit of walking involved.

Shuttles: This is definitely not a fitness event, but stations are spaced out throughout downtown. Don’t worry, 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 shuttles 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: heather@downtownmiddletown.org.