The Race to Mackinac, the longest and oldest freshwater annual sailing competition in the world, is here. On Friday and Saturday, roughly 245 boats carrying more than 2,000 crew members will sail for Mackinac Island, the resort destination off the northern tip of Michigan’s Lower Peninsula.

Here’s your primer.

Race basics

For 333 miles — or 289.4 nautical miles — 245 entrants, give or take last-minute dropouts, will traverse the route from Navy Pier to Mackinac Island in this year’s event, according to Sam Veilleux, chairman of the 2023 race committee. The first Mackinac race took place in 1898, with just five boats, and the second was in 1904. With the exception of several years during World War I and 2020 during the pandemic, the race, organized by the Chicago Yacht Club, has happened every year, marking its 114th running this year. Competitors may enter the race, classified as an amateur event, by invitation only.

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The majority of entrants travel to the race start via water — meaning they’re coming from harbors in or near Chicago or traveling from cities along connected lakes, mostly Michigan and Huron.

“Every year, we do have a few out-of-town boats that come from the coast, but it is quite an endeavor,” Veilleux said, noting that delivering a large yacht on a truck involves reassembling the boat in Chicago after shipment. Past races have included crews and boats from Australia, New Zealand and Hong Kong.

As described by Veilleux, the route starts at the Chicago Lighthouse, near Navy Pier, and runs the entire length of Lake Michigan, passes through Grays Reef, enters Lake Huron through the Straits of Mackinac, ducks under the Mackinac Bridge and finishes at Mackinac Island.

How a crew wins and what they get

First to the island wins, right? Not quite.

The Chicago Yacht Club describes the Race to Mackinac as “a unique race, where the boat equivalent of ‘family sedans’ compete against ‘Formula One cars.’ ” What this means in practical terms is that boats, which range widely in technical capability, must be assessed in advance in order to be properly grouped by similar ratings. An algorithm takes boat measurements — including weight, size, sizes of the sails and more — to produce the standardized ratings.

The entrants compete in two divisions: cruising and racing. Boats in the cruising division are, according to Veilleux, “generally more comfortable” equipped with cabins, galleys and full accommodations.

“Boats that you’d go on, for example, a family cruise around the Great Lakes or around the Caribbean,” he said. There are three sections within this division, each based on speed.

Yachts in the racing division are built for speed — lightweight carbon-fiber hulls, sparse interiors — and compete in two section types: one in which the boats have identical specs, and another in which boats are handicapped, as in golf, based on relative performance characteristics.

Roughly split in half into “faster” and “slower” groups, the racing division is then further divided into similarly rated sections — this year there are 18, each with around 12-15 boats. The winner is determined by calculating time against a boat’s rating.

Sailors compete for three main honors: the Mac Trophy and the Mac Cup for the racing division, and, new this year, the Whitehawk Trophy for the overall winner in the cruising division. Each year, the two groups in the racing division — one faster, one slower — alternate between competing for the Trophy and the Cup so crews could possibly have their names engraved on both if they raced in consecutive years. The first three places in every section also receive a brag flag to display on their boat.

To be invited to the exclusive Island Goats Sailing Society, racers must have competed in at least 25 Chicago-to-Mackinac races, for a total of about 8,325 miles. Founded in 1959 by Hobart “Red” Olson, the society was named after sailors’ “appearance, aroma and behavior upon reaching Mackinac Island,” according to the Chicago Yacht Club website.

When can we expect results?

Most of the fleet takes from 40 to 60 hours to finish the race. Cannons will fire to release the cruising sections at 3 p.m. Friday, and the rest of the sections start from 11 a.m. Saturday every 10 minutes until 3 p.m.

To race around the clock, the crews sail in shifts. The multihull record was set in 1998 at under 19 hours, and the monohull record was set in 2002 at under 24 hours. Ideally, racers finish on or before Monday so they have time to rest before the awards ceremony Tuesday. While there’s no publicly available record of the longest time a boat has taken to finish the race, Veilleux said the club has a system for sailors to submit their final times even after the finish line is taken down on Wednesday.

During last year’s race, Veilleux said wild storms battered the fleet for about 12 hours on Lake Michigan, causing 29 boats to drop out. Veilleux competed last year in the cruising division and, although only sailing on the edge of the storm, experienced wind in excess of 55 knots.

“That’s like sticking your head out of a car window at highway speed,” he said.

Chuck Nevel, the club’s on-the-water director, stays on the island to direct boats as they complete the race. Once the boats start streaming in, they don’t stop. Neither do their supporters.

“If it’s 2 a.m. or if it’s 10 a.m., there are people out there cheering their family members on, their friends on, especially if it’s their first Mac,” he said.

“Everyone stinks, hasn’t taken a shower, sweating in their weather gear,” Nevel notes of the state of the crews as they disembark. But he concedes the members of the race committee, who work through the day and night to make sure everyone arrives safely into port, aren’t the freshest smelling bunch either.

One word for the atmosphere of the awards ceremony? “Jubilation.”

How to watch the race

From 2:30-3:30 p.m. on Friday, the start of the race for the cruising division will be livestreamed on CBS.

On Saturday, you can watch the parade of boats in the racing division off the end of Navy Pier from 10 a.m. to 1 p.m. An announcer will provide details of the vessels as they sail toward the start. Viewers should also be able to see the rigs from anywhere along the lakefront north of Navy Pier.

Race updates will be available on the Chicago Yacht Club’s Facebook, Instagram and Twitter feeds. But perhaps the best way to follow the race is to view each boat’s progress through the event’s race tracker website or via mobile app, which will become available on Thursday of race week. Download the YB Tracking app and “buy” the Chicago Yacht Club Race to Mackinac (it’s free).

Finally, why is it spelled “Mackinac” but pronounced “Mackinaw?”

Originally named Michinnimakinong by the Ojibwa tribe, the indigenous translation refers to the large crevice in the island: “mish” meaning great, “inni” meaning connecting sound, “maki” meaning fault and “nong” meaning land or place. The name was shortened to Mackinac by the French, and the British transcribed it phonetically as Mackinaw. Edgar Conkling, founder of Mackinaw City in 1857, was the one to spell it with a “w.”

Either way, the pronunciation is “MACK-in-awe.”

Ysa Quiballo is the digital news intern at WBEZ. Courtney Kueppers contributed.