Community members enjoy a Friday evening at Dine Out Downtown on Friday, May 21. The event features live entertainment and provides an opportunity to eat a meal from a local restaurant outdoors on Third Street.

A pandemic pivot Winona is keeping




Even a bout of heavy rain did not dampen area residents’ enthusiasm about the first Friday evening of Dine Out Downtown this year. Part of Third Street was closed off from traffic and turned into an open air cafe. When the drops started to fall, event attendees simply dashed to the sides of local businesses with overhangs or braved the weather under the umbrellas at the tables along the road. The rain soon passed, and community members then cheered on musicians playing solos during a drum line performance. Attendees next returned to their discussions and food as other live music began. With that, the weekly event started its 2021 run last Friday. 

Dine Out Downtown, a Main Street Program event, began last year as a way to provide local businesses with an opportunity to expand their outdoor dining areas and hold outdoor events such as sales every Friday night over the summer, in light of the pandemic causing indoor dining to be prohibited or limited at different times. The event is back this year. A Dine Out Downtown organizer and several local business owners said they hope the event continues to grow through the addition of more activities, such as live entertainment, and increased participation from community members and businesses. 

The business owners and organizer agreed that the event is valuable because it brings people downtown. “Our downtown is an extremely valuable asset to our community, and being able to allow people to have greater access to it on a weekly basis really just allows community members and tourists to come and see some of the things our downtown has to offer,” Main Street Program Manager Ben Strand said. 

Winona community member Danielle O’Laughlin and her children attended Dine Out Downtown last Friday. They went because they appreciate Blooming Grounds and live music, and they had enjoyed soaking up good weather at the event in the summer of 2020. “I think it’s a great event, and we’re so proud of Winona for having events like this, because I think it adds to the character of the town,” she said. 

O’Laughlin also knew the Winona Little Warriors, an area children’s drum line, would be performing, and her children would be excited to witness it. “So we were just kind of hovering, waiting for them,” she said. “I think it’s good to have them see kids doing music.” 

O’Laughlin plans to come back for the event as much as possible throughout this summer so she can keep “supporting as many downtown businesses as we can … supporting some of the places that we love that we don’t want Winona to lose.” 

Some local business owners said they felt that support from community members during Dine Out Downtown last year. Nate and Ally’s Owner Dennis McEntaffer and Jovy Rockey Jewelry Owner Jovy Rockey said the event seemed to motivate more people to go downtown. “Anything that attracts people to downtown, whether it’s for shopping or other restaurants, always helps us,” McEntaffer said. He added, “It gives people an opportunity to realize how many eating places we have downtown. And it’s something different, so it attracts those people who lots of times don’t come downtown to eat or just to be downtown.” 

Looking ahead, Strand said event organizers plan to provide attendees with different entertainment each week this summer. Some of the organizers’ ideas include dancing, a performance by a local marching band and poetry activities. There is room to grow with increasing foot traffic through such entertainment, he said, and that foot traffic may spill over into business at retailers. 

McEntaffer also said he hopes Dine Out Downtown keeps expanding “so that it is something good that has happened that was caused by the pandemic.” 

In the meantime, Rockey and Strand said the event could serve as a community building activity. Dine Out Downtown gives people a chance to be together outdoors during the pandemic, Rockey said. “The opportunity to share space with someone else is huge,” she said. Strand said he hopes those who go to the event gain “a sense of belonging to the community, a sense of comradery, an ability to get together with family and friends.” 

Dine Out Downtown will take place on Third Street from 4 p.m. to 10 p.m. on Fridays through September 24.


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