If you’re looking for an all-inclusive drink package on a cruise but don’t have a Carnival or Norwegian budget, consider the 2025 Women’s Wine and Chocolate Walk in Middletown.
This Saturday, May 17, downtown Middletown will transform into a nautical party for the 12th-annual Women’s Wine & Chocolate Walk. 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. This year’s “Let’s Cruise!” theme gives a nod to the Miami and Erie Canal, kicking off the canal’s bicentennial celebrations in downtown Middletown.
“There’s different zones that are like different ports,” said event volunteer Melodie Rickard. “We have the Hawaiian, the Mediterranean, the Caribbean and the Alaskan. All the businesses are asked to decorate in their zone theme.”
The format is simple: Ticket holders will check in at the Windamere on South Main Street to pick up a wine tasting glass, swag bag and tasting map. Pick your check-in time when you purchase your tickets online. Choose from either noon-1 p.m. or the 1-2 p.m. slot; organizers tell CityBeat the noon time slot is filling up fast, so consider the 1-2 p.m. option. There’s also a VIP option, which includes bonus wine and chocolate tasting and allows you to check in between 11:15 a.m. and noon.
Then you’re off! From your check-in time until 6 p.m., a tasting map will guide you to 10 wine stops and 10 chocolate stops throughout downtown Middletown. If you’re not much of a wine fan, downtown restaurants will be offering to-go drink specials to enjoy in the DORA district. There’s also plenty more to do than just drink and eat chocolate — shop local vendors and boutiques, play activities and boat-themed games or simply dance around with your pals as a live DJ turns downtown Middletown into a giant party.
Guests are also encouraged to lean into the cruise theme by donning Hawaiian shirts, sunglasses, captain hats and other vacay attire. Comfortable shoes are recommended for the wine walk, but a free shuttle will be available to drop you off near the farthest stops throughout the event.
Proceeds from Middletown’s Women’s Wine and Chocolate Walk serve as a fundraiser for Downtown Middletown Inc., supporting dozens of small businesses. In CityBeat’s Best of Cincinnati 2025, Middletown’s Women’s Wine & Chocolate Walk earned high praise for its laid-back party vibe:
The Middletown Women’s Wine & Chocolate Walk is a lot cooler than you think. Blocks of downtown Middletown are reserved for local ladies to shop, sip and snack while a DJ plays hits that will take you (and your mom) back to slumber parties past. One ticket gets you a swag bag, tasting map and wine glass – which you’ll need as your companion for the 10 different wine stops and chocolate stops throughout downtown Middletown. Along the way, shop for everything your home and wardrobe needs (or doesn’t, but still wants) while you run into friends old and new. If wine isn’t your cup of tea, a handful of restaurants will offer to-go drink specials that will make you dance in the street and sing into your cup like it’s a hairbrush. If you thought the Women’s Wine Walk was just for your mom’s friends from high school, note that I found myself dancing in Central Pastry bakery with total strangers in broad daylight like it was the club. In that moment, it was.
If you don’t feel you fit the ladies’ party demographic, Rickard said Broken Barrel on Central Avenue will offer a “husband day care” for the fellas.
“If the guys drop their wives off downtown, they just go a couple blocks up the road,” Rickard said. “There’s going to be food and drink specials at Broken Barrel. They’re looking forward to that.”
Tickets for Middletown Women’s Wine & Chocolate Walk range from $58 to $79 and can be purchased here.
This article appears in Apr 30 – May 13, 2025.
