Women's Wine & Chocolate Walk 2025

***Ticket Presale - Saturday, March 8, noon-4pm. Purchase tickets at Triple Moon Coffee Co or online for the best rates available. Buy in-person to get a free gift and be the first to get this year's t-shirt! ***

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 an item to Adam's Hope (more details below). 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.

Theme: Let's cruise! Every year we celebrate with a new theme. This year we are crusing on vacation. Grab your tickets because you won't want to miss all the amazing ports of call on our cruise through downtown Middletown.

Ticket Sales: Catch the BEST rate available by purchasing tickets during the Ticket Presale on Saturday, March 8, noon - 4pm. You can buy tickets in-person at Triple Moon Coffee Co or online. When you purchase tickets in-person, you get a free mini cruise kit gift, and we will have the first release of souvenir t-shirts available for purchase.

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

SuperStar VIP Package: This is 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, 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. NEW - we are expanding our VIP space this year. We will have more room, more tables, and more seating for you to enjoy your VIP welcome party.

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 one of our soft ladies v-neck shirts. With a small logo on front and cute cruise design on back, it's the perfect tee to wear to the event or just around town.

If you purchase a shirt online, you may pick it up at Design 2 Wear 2 the week of the event or at the Women's Wine & Chocolate Walk.

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.

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 pick which baskets you would like to enter to win.

If you want a FREE raffle ticket, donate an item to Adam's Hope, an organization sending care packages abroad to military communities. They need items like men's hygiene products and snacks. Please check the FAQs for a donation list. Upon making a donation, you will 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.

What to Wear: Get ready for an afternoon of cruise-themed fun. Wear matching cruise shirts with your crew, a sun dress with your favorite straw hat, or whatever reminds you of being on a fantastic cruise vacation. 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]

Please note, we do not offer refunds, but you are welcome to pass along an unused ticket to a friend!

Event Venue & Nearby Stays

Downtown Middletown - Check in at The Windamere, 2 S. Main St., Middletown, United States