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Upcoming Events › Outdoor Events

November 2019

2019 Holiday Window Walk: “Walking in a Window Wonderland”

November 29 - December 31

Deck your window displays out with a North Pole setting of your choice! The winner of the best decorated storefront will be announced at a social during December’s “Third Thursday Night Out” on the 19th.

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December 2019

Christmas Lighted Parade

December 7 @ 5:30 pm

The lighted parade route is located at 41st Avenue & 6th Street to 44th Avenue. After the parade, members of the Winona Elks Lodge #327 will be serving food and refreshments along with some fun activities at the Elks Lodge in Goodview. There will be a bake sale for you to satisfy your sweet tooth, face painting, and fun activities for everyone! Also there will be two bicycles given away for two lucky kids! Hosted by the Goodview Activity Group,…

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Canadian Pacific Holiday Train

December 9 @ 4:00 pm - 4:45 pm
Amtrak Depot, 65 East 11th St., Winona, 55987

The CP Holiday Train will set out once again to entertain hundreds of thousands of people, collecting food and raising funds for food banks across North America. The train will stop at the Winona Amtrak Depot and performers are Meghan Patrick, Tanika Charles and Kelly Prescott.

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Winona Holiday Market

December 14 @ 12:00 pm - 4:00 pm

It’s the return of the Winona Holiday Market.  Great artisan gifts, food trucks, holiday beverages, and free ice skating- all from 12-4pm, steps from the Mississippi in our beautiful Levee Park.

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April 2020

100 Mile Garage Sale

April 30, 2020 - May 3, 2020

Residents and stores clean out their attics, garages & basements to create the Most Spectacular Garage Sale. A trail of distinctive colored ribbons will identify participating garage sales from Alma on the southern end of the Wisconsin side of Lake Pepin, north along Hwy. 35 through Nelson, Pepin, Stockholm, and Maiden Rock to Bay City, WI. The trail then crosses west to Minnesota at Red Wing, MN and heads south on Hwy. 61 through Frontenac, Lake City, Camp LaCupolis, Reads…

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June 2020

Trinona: The Battle for the Bluff

June 13, 2020 - June 14, 2020

The World’s Biggest Little Triathlon. With every stroke, pedal and stride during Trinona, you’ll encounter incredible views and beautiful terrain. It will begin at dawn, as you set up in transition in front of Lake Winona and look up to see Sugarloaf Bluff rising above the town below. Following the swim, you will begin your journey into the true calling card for this event, the Mississippi River Bluff Country.

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Steamboat Days

June 17, 2020 - June 21, 2020

Winona Steamboat Days is Winona’s feature festival. Steamboat Days includes a Carnival, Beverage Garden with entertainment, Kid Fishing Contest, Kid Pedal Pull, Kiddie Parade, Grande Parade, Fireworks and a whole lot more.

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July 2020

Winona County Fair

July 8, 2020 - July 12, 2020
St. Charles Fairgrounds, 506 W. 6th St., St. Charles, Minnesota 55972

Winona County Fair features dairy cattle, dairy goats and meat goats, beef cattle, sheep, poultry and pigeons, farm crops, vegetables, organic crops and vegetables, horticulture, plants and flowers, baked goods, food preservation etc.

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American Duchess Docking

July 14, 2020 @ 8:00 am - 5:00 pm

The American Duchess will dock at Levee Park from 8:00 a.m. – 5:00 p.m.  There will be no public tours but the public is invited to welcome the passengers and get a close look at the steamboat. The American Duchess is the most elegant paddlewheeler on U.S. rivers, a floating, intimate masterpiece that can carry up to 166 guests through America’s heartland. The paddlewheeler, created from a 1995 hull, was completely reconstructed to become one of the most luxurious river cruising vessels…

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Tour of Gardens: Bursting with Blooms

July 18, 2020 @ 8:00 am - 3:00 pm
Garden tour Winona Minnesota flowers Women's Resource Center

“Bursting with Blooms” tour of gardens features a total of six gardens.

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