Halloween Dreams: Nightmare on Orange Returns to The Courtesy

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With one month until their first Winter Park anniversary, Diana Zimmerman and the staff of The Courtesy bar are prepping for a party they had to miss last year.

“We started Nightmare on Orange in 2018 and were able to do it every year but one,” she told the32789. The move from their former downtown Orlando address to the new space at 1288 N. Orange Ave. was followed by a grand opening on Oct. 14, 2022, that left no time to plan for the spooky celebration. However, the new digs have inspired some new additions for its anticipated return.

Zimmerman, along with co-owner and husband Gene Zimmerman, based Nightmare on Orange on the “Miracle” holiday season pop-up by international barware distributor Cocktail Kingdom. The local version, dubbed Miracle on Orange, made its Winter Park debut last November after five years at The Courtesy’s former location. Unlike the Cocktail Kingdom partnership, which provides barware, decor and a preset drink menu to select cocktail bars around the world, Nightmare is purely local.

“It’s our thing and it’s really fun for us,” said Diana. “The staff creates all the drink recipes and we shut down for a day to decorate; it’s a total group effort.”

Adjusting from The Courtesy’s former, smaller space means efforts are being stepped up with additional decorations and new barware – which, unlike the Miracle promotion, is not for sale. The event menu of 12 drinks will also include two specialty shots a mocktail. One alcoholic offering, the “Please Take One,” is inspired by the taste of a Snickers bar.

According to Zimmerman, increasing the inventory to accommodate more guests has presented an interesting challenge that involves lots of retail savvy. “If I can only find six or eight of a particular barware design I have to pass,” she said. “We need a lot more than we had at the old location and consistency is important. There have been a lot of late nights on the internet.”

Despite the larger space, the popularity of the Halloween event will require a crowd control element that Zimmerman admits was needed during last year’s Miracle on Orange. Long lines and two-hour wait times may be common for a theme park, but Zimmerman wants something better for her guests.

“Quality of service and enhancing the guest experience has always been important to us. If people waited for two hours to get into Miracle they might have come in a little grouchy and it would have taken away from the experience.”

An online reservation system was recently launched in anticipation of the busy holiday season. Parties of four or more can reserve a two-hour experience with a down payment of $10 per person. More time is available depending on the size of the group. Parties of three or less remain first come, first served.

“We started two months ago just to get the process going, and it’s working,” said Zimmerman. “Once we get into the themed pop-ups we will be encouraging any party over four people to make reservations. If you’ve got six or eight people, there’s a good chance you won’t be able to get in without it.”

Nightmare will run Oct. 3-31 with a three-week break before Miracle on Orange begins. During that time, the decor will return to normal, but the fall flavors of the Halloween drink menu will perfectly bridge the holiday gap and remain available until the Miracle menu is served.

Zimmerman sees the timing of both seasonal pop-ups as a way to celebrate the first year in Winter Park. The success has inspired a few ideas – still in development – for incorporating the courtyard area and neighboring businesses in event planning, and she looks forward to the opening of the nearby Seven Oaks Park as an added attraction. While she enjoys the new space and neighborhood, she is thankful for some things that haven’t changed.

“I’m grateful for how much of our longtime clientele followed us over,” she said. “And the welcome we’ve received from Winter Park guests who are coming in for the first time has made this year a really special experience.”

More information on the seasonal pop-ups, weekly offerings and reservations are available at thecourtesybar.com.

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