Women’s Wine & Chocolate Walk 2025!

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.

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 8.

Raffle: Last year we had amazing baskets full of local goodies, jewelry, an airplane ride, and of course wine. When you purchase your raffle tickets online, you will get your printed raffle tickets when you arrive at the event and choose which baskets you would like to put them toward.

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. This year’s theme is “Let’s Cruise!” Come in matching shirts with your friends, wear a sundress and straw hat, or dress in whatever reminds you of a cruise vacation. You can also wear the 2025 Women’s Wine & Chocolate Walk shirt, available for order on Eventbrite. We have A LOT of fun with this! The theme will be announced in March. Remember to wear 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.