Women's Wine & Chocolate Walk 2025

Ladies Day Out

Join us for the 12th annual Women's Wine & Chocolate Walk. Grab a group of ladies to sample wine and chocolate while visiting dozens of local stores, vendors, and restaurants. 

This year's theme is: "Let's cruise!" All aboard for this cruise-themed adventure. Grab your tickets soon because you won't want to miss all the amazing ports of call on our cruise through historic downtown Middletown.

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!

Links & Tags

The Windamere

Women's Wine & Chocolate Walk 2025 is taking place at The Windamere, which is located at 2 S. Main St. in Middletown. The Windamere - Event Venue and Art Gallery. Our historic venue can accommodate up to 175 guests on the main floor with a dance floor. Additional seating is available in the twin balconies.