Middletown's 'Women's Wine and Chocolate Walk' Gives Guests a Tour of Historic Downtown

The event's theme for 2024 is 'Pop Stars Through the Eras.'

Apr 29, 2024 at 2:35 pm
Women stop at Central Pastry bakery during the 2023 Women's Wine and Chocolate Walk in Middletown.
Women stop at Central Pastry bakery during the 2023 Women's Wine and Chocolate Walk in Middletown. Photo: Courtesy Downtown Middletown Inc.

Downtown Middletown Inc. will host its 11th annual Women's Wine and Chocolate Walk on Saturday, May 18 with a refreshed theme to draw out the pop star in us all.

Like a bar crawl with something for everyone, ticket holders can taste different wines and chocolate treats while walking across Middletown's historic downtown business district. Guests will check in at the Windamere, a historic event space on S. Main Street, where they can pick up a wine tasting glass, swag bag and tasting map that will guide them to 10 wine stops and 10 chocolate stops throughout downtown Middletown. The event lasts from noon to 6 p.m.

Downtown Middletown Inc. events director Heather Horine tells CityBeat that guests will definitely get their steps in, but it's no race.

"It is definitely not a fitness event. We call it a walk because we want to get women around the downtown area in the different businesses, just exploring and seeing different areas down there," Horine said. "Ladies can walk from stop to stop at their leisurely pace; they get some chocolate, get some wine. It's a lot of socializing, a lot of just catching up with people you haven't seen in a while, running into old friends, making new friends."

Ticket holders can sample wine and chocolate from dozens of bars, restaurants, shops and booths in the historic downtown, including:
  • The Windamere/Launch Lab (check-in and VIP)
  • Gravel Road Brewing
  • Whistle Stop Shop
  • Iron Rose
  • Merkel's Tavern
  • Monarch Designs (PAC artist)
  • N.E.W. Ales
  • Primo Italian Steakhouse
  • Sorg Opera House
  • The Swire Inn
  • West Central Wine
  • White Dog Distillery
  • Art Central Foundation
  • Central Pastry Shop
  • Connections Day Spa
  • Crooked Dog Comics
  • Design2Wear2
  • Foodeez
  • Jackson Lane Design
  • Pudgy Pony
  • Pendleton Art Center (PAC)
After more than a decade of the Women's Wine and Chocolate Walk, Horine tells CityBeat the event consistently draws out-of-town visitors to experience Middletown's growing downtown economy.

"We really just want to show people that downtown Middletown is a thriving place. There's a lot of variety, everything from coffee shops to fancy steak houses and bars and shows and cute little shops," Horine said. "We've sold tickets in Cincinnati, Dayton, Columbus — we've sold tickets from different states — it's really cool to see those pop up on our ticket sales."
click to enlarge Guests shop the booths at the 2023 Women's Wine and Chocolate Walk in downtown Middletown. - Photo: Courtesy Downtown Middletown Inc.
Photo: Courtesy Downtown Middletown Inc.
Guests shop the booths at the 2023 Women's Wine and Chocolate Walk in downtown Middletown.

A star-studded theme

Whether you're walking from shop to shop or taking advantage of the event's free shuttle service, guests are invited to boogy to musical entertainment along the way, including a DJ at Governor's Square and outdoor karaoke near White Dog Distillery. Guests are encouraged to dress as their favorite pop music icon as they stroll through different musical eras from stop to stop.

"Our theme is "pop stars through the eras," Horine said. "We're actually going to divide the downtown area into different eras. In the first era, we'll play music from the 2000s to present day and we've encouraged our businesses in that era to dress appropriately. I know at one [business] all their workers are dressing like Britney Spears that day. They're having a lot of fun with it. We'll also bring in some fun pop culture history about Middletown, which we've never done before."

Buying tickets

General admission tickets can be purchased on the event page for $55 or $75 for a VIP ticket, which gets you early admission, a bonus wine and chocolate tasting and light bites at the VIP welcome reception. For $750, the "Super Star VIP Package" gets five guests a mimosa brunch before the event, one hour of a chauffeured golf cart, five bottles of wine, 10 raffle tickets, front-of-the-line VIP access and a swag bag for each guest.

All guests will select a specific check-in time upon booking. Guests are also encouraged to bring a personal hygiene item, cleaning supplies or a non-perishable food donation in exchange for a free raffle ticket at check-in. All donations will benefit St. Vincent de Paul.