{"id":2861,"date":"2026-08-04T09:50:11","date_gmt":"2026-08-04T16:50:11","guid":{"rendered":"https:\/\/theaposition.com\/traveltattler\/?p=2861"},"modified":"2026-08-04T11:36:50","modified_gmt":"2026-08-04T18:36:50","slug":"tales-from-the-great-lakes-as-brave-sailors-race-from-chicago-and-port-huron-to-mackinac","status":"publish","type":"post","link":"https:\/\/theaposition.com\/traveltattler\/golf\/courses-and-travel\/2861\/tales-from-the-great-lakes-as-brave-sailors-race-from-chicago-and-port-huron-to-mackinac","title":{"rendered":"Tales From the Great Lakes as Brave Sailors Race From Chicago and Port Huron to Mackinac"},"content":{"rendered":"
\"Mission<\/a>

At the Watery Finish Line with Mission Point Resort\u2019s Liz Ware. Photo by: Emily Daunt, MRLA<\/p><\/div>\n

The world\u2019s oldest, continuous freshwater sailboat races take place each summer across two Great Lakes over consecutive July weekends: the Chicago-to-Mackinac and Port Huron-to-Mackinac races. It\u2019s hundreds of nautical miles and two or three dramatic days and nights on the water for thousands of sailors on a barrage of boats steered by crew members peering through the mist and humidity for their first sight of the towering \u201cmighty\u201d Mackinac Bridge. But it is the traditional sound of a colonial cannon firing that booms each boat\u2019s finish across the official line at the Round Island Lighthouse at Windemere Point.<\/p>\n

Once docked, the Pink Pony Saloon, managed for decades by Brian Bailey and owned by Bob Benser, is the closest immediate relief for the parched, soggy sailors. They deserve a bit of booze before the big bash on the Great Lawn at Mission Point Resort, where the Aperol and awards are poured and presented to the thousands in the formal, shoreline ceremonies a day after each race.<\/p>\n

The sailboat racing and events, staged since 1898, may sound as genteel as Mackinac Island\u2019s horse-drawn, Victorian-era luxury lodging. But, usually with a \u201cDark-n-Stormy\u201d rum drink in hand, the sailors tell tall tales of walls of waves, storm-shredded spinnakers, and, conversely, the dreaded doldrums.<\/p>\n

\u201cWhen it\u2019s really hot with no wind, they sit in the sun and deal with flies out there on the lakes,\u201d said Liz Ware, chair of the Michigan Travel Commission. She and her family own Mission Point Resort. \u201cThat\u2019s one of the reasons I have made the trip from Chicago across Lake Michigan to Mackinac Island by powerboat, but not on a sailboat. The races are for people who are really tough, rugged and strong. The conditions they manage range from great wind, no wind, and storms. I have such respect for the really great sportsmen and women who compete in these races.\u201d<\/p>\n

Birmingham, Michigan songwriter and singer Robert Dempster was on the crew of Jim Leamon\u2019s 36-foot boat Trim. \u201cOh yeah, my guitar has got to be with me to play some music and maybe chase away the black flies,\u201d Dempster joked.<\/p>\n

\u201cRobert Dempster is the most motivational man that I know,\u201d said Captain Leamon, who needed Dempster, all hands on deck, when Trim and hundreds of other boats had to turn back off Port Sanilac, in Michigan\u2019s Thumb, four hours after their Port Huron start. \u201cAn intense storm with 15-foot waves took us and half the fleet for a ride like Disneyland. Water crashing over the bow made the boat more like a submarine.\u201d<\/p>\n

Captain Leamon made the decision to turn back when sustained 35-knot winds with overpowering gusts to 45 were knocking their boat dead out of the north – the direction they needed to sail. It was all the crew could do to get the boat to a nearby harbor safely.<\/p>\n

\u201cI was in a \u2018sea shock.\u2019 When I got to the dock in Port Sanilac, I kissed the ground,\u201d said Dempster. \u201cIt was a Great Lakes adventure for sure.\u201d<\/p>\n

It wasn\u2019t a storm at the start of the Chicago version of the race, but a collision with another boat that nearly sank the 50-foot yacht MC2, according to Shari Lewis. Her husband was at the helm when the crew discovered the crash broke a two-by-four-foot hole in the port side of the hull.<\/p>\n

\u201cThey kept racing and bailing water every 20 minutes for hours while trying to patch the hole. They figured they took 200 gallons of water off the boat until they came up with a solution that worked: they pulled apart a Yeti cooler and used a bunch of other materials,\u201d said Lewis.<\/p>\n

Amazingly, MC2 reached Mackinac Island fast enough to still finish in third place! The crew then sailed her to Port Huron, where the boat underwent fiberglass and epoxy repairs just in time for\u00a0Saturday morning\u2019s start of the Port Huron-to-Mackinac race. MC2\u2019s crew, with little sleep, then managed to sail through the aforementioned fierce storm on Lake Huron that ended the race for more than 80 boats.<\/p>\n

\u201cThey hung on and never had an issue with the repair work,\u201d said Lewis. \u201cThe grit, determination and tenacity of this crew is just unmatched. They’re like extended family to us.\u201d<\/p>\n

The Ware families\u2019 waterfront Mission Point Resort is the award-bash venue for both races when thousands of sailors gather on the resort\u2019s Great Lawn, and a great view of the lake they just conquered, from an Adirondack chair. The rest of the season, Mission Point is where the Midwest puts its feet up.<\/p>\n

Contact Michael Patrick Shiels at\u00a0<\/em>MShiels@aol.com<\/em><\/a>\u00a0\u00a0His new book: Travel Tattler \u2013 Not So Torrid Tales, may be purchased via\u00a0Amazon.com\u00a0Hear his radio talk show on 730\u00a0AM 1240\u00a0in Lansing weekdays\u00a0from 3 pm \u2013 6 pm.\u00a0<\/em><\/p>\n

\n","protected":false},"excerpt":{"rendered":"

The world\u2019s oldest, continuous freshwater sailboat races take place each summer across two Great Lakes over consecutive July weekends: the… Read more »<\/a><\/p>\n","protected":false},"author":43,"featured_media":2862,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[17],"tags":[1019765,1044573,1044574,1044575,1044576,1044577,1044578,498928,1044579,3427,1044580,4998,575006],"class_list":["post-2861","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-courses-and-travel","tag-great-lakes","tag-liz-ware","tag-mission-point-resort","tag-robert-dempster","tag-jim-leamon","tag-shari-lewis","tag-port-huron-to-mackinac-race","tag-mackinac-island","tag-chicago-to-mackinac-race","tag-chicago","tag-pink-pony-saloon","tag-michael-patrick-shiels","tag-michgan"],"jetpack_featured_media_url":"https:\/\/theaposition.com\/traveltattler\/wp-content\/uploads\/sites\/34\/2026\/08\/unnamed-file.jpeg","_links":{"self":[{"href":"https:\/\/theaposition.com\/traveltattler\/wp-json\/wp\/v2\/posts\/2861","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/theaposition.com\/traveltattler\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/theaposition.com\/traveltattler\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/theaposition.com\/traveltattler\/wp-json\/wp\/v2\/users\/43"}],"replies":[{"embeddable":true,"href":"https:\/\/theaposition.com\/traveltattler\/wp-json\/wp\/v2\/comments?post=2861"}],"version-history":[{"count":2,"href":"https:\/\/theaposition.com\/traveltattler\/wp-json\/wp\/v2\/posts\/2861\/revisions"}],"predecessor-version":[{"id":2864,"href":"https:\/\/theaposition.com\/traveltattler\/wp-json\/wp\/v2\/posts\/2861\/revisions\/2864"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/theaposition.com\/traveltattler\/wp-json\/wp\/v2\/media\/2862"}],"wp:attachment":[{"href":"https:\/\/theaposition.com\/traveltattler\/wp-json\/wp\/v2\/media?parent=2861"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/theaposition.com\/traveltattler\/wp-json\/wp\/v2\/categories?post=2861"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/theaposition.com\/traveltattler\/wp-json\/wp\/v2\/tags?post=2861"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}