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"The cutest little small town celebration": Oh Ole Night 2023 lights up the start of the holiday season

Nov 27, 2023 04:52PM ● By Content Editor
All photos and video by Laura Durenberger-Grunow

By Laura Durenberger-Grunow - Boreal Community Media - November 27, 2023

It's an annual tradition that feels right out of a cheesy holiday movie in the best way: Visit Cook County's Oh Ole Night

The event takes place the Friday after Thanksgiving in downtown Grand Marais in late afternoon/early evening, and starts with a holiday parade open to anyone who wants to participate. Spectators line up along the street enjoying homemade holiday cookies from Crosby Bakery or a Skizzle from World's Best Donuts, and watch as floats go by, twice, decked out in festive decorations. 

Visit Cook County, the organization that puts on the event, gives awards to different floats each year. The 2023 year winners are:
  1. Traveling Gnome Award: Buck's Hardware
  2. Most Holiday Spirit Award: Coldwell Banker
  3. Biggest Float Award: Cook County Towing
  4. Most Adorable Animal Award: Ann Sullivan with Tundra
  5. Cutest Kiddo Award: The Chocolate Dog
  6. Best Scandinavian Award: The Norwegian Elk Hounds, Ruffin & Rawnya

After the parade, attendees gather in Grand Marais' Harbor Park for the lighting of the Christmas Tree. This year the tree was donated from a farm in Grand Rapids, MN to the city of Grand Marais, according to the Cook County News Herald. This year, the lighting ceremony countdown was led by Grand Marais Mayor Tracy Benson. You can watch the full tree lighting portion of the event below. 

Immediately after the tree lighting, fireworks were launched over Grand Marais harbor to finish the evening. 

 Oh Ole Night attendees begin arriving on Friday lateW afternoon/early evening for the event

 World's Best Donuts opened especially for the event to sell Skizzles 

 Sugar, chocolate crinkles, and ginger cookies were available for all to enjoy

 The crowd eagerly awaits the start of the parade

 The Color Guard marked the start of the parade

 Coldwell Banker won the Most Holiday Spirit award

 Cook County Towing won biggest float award

  Cook County Towing won biggest float award

 Cook County Highway Department brought out the MVP of winter

 Siverton Art Gallery honored Howard Siverton with the Red Suspenders Club

 The Chocolate Dog is a new endeavor from Chelsea Pusc, who recently announced the closing of her current business Gunflint Mercantile in February. The float also won "cutest kid award".

 Buck's Hardware won the Traveling Gnome award

 Goats even joined in on the fun!

 The Norwegian Elk Hounds, Ruffin & Rawnya won Best Scandinavian Award

 Java Moose employees and family were all decked out in festive gear

 Stone Harbor Wilderness Supply and Santa signaled the end of the parade

 The crowd counts down from 10 during the tree lighting ceremony

 Fireworks over the harbor


Boreal Ship Spotter - larger view here