Today marks the end of a historic — but much too prolonged — era and the dawn of what racing proponents hope will be a brave new chapter. But, as much as it is a crossroads, the 150th Preakness Stakes will be a peculiarity.

Mercifully, it’s the final one at the original, crumbling Pimlico Race Course. Less than 48 hours after the 150th Preakness champion is crowned, state archivists will remove pieces of Pimlico for preservation on Monday and, six weeks later, excavators will begin to demolish the venue.

Then begins an ambitiously tight timeline to rebuild the structure within 22 months.

For many frustrating years, racing and state officials failed to come up with a satisfactory path to a renovated Pimlico. The track’s old grandstand was supposed to be razed, according to legislation, two years ago.

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That didn’t happen, but now, at long last, a concrete plan appears in place. When demolition (which will use machinery but not explosives or a wrecking ball) begins, it will leave the Preakness without a permanent home — necessitating that the blueprint to rebuild Pimlico is successful.

Once the grandstands and venue come down, “there’s no turning back,” said state Del. Sandy Rosenberg, whose district includes the Park Heights community.

Today, for one last time, the roar of a Preakness crowd will echo off the condemned grandstand and patrons’ complaints about missing ceiling tiles and bathroom problems will murmur through the outdated clubhouse.

After a pit stop at Laurel Park next year, the Preakness is scheduled to return to a shiny new Pimlico in May 2027, provided the construction timeline proceeds as scheduled.

This year’s Preakness will also occur in the midst of a baton handoff from one operator to another. The Canadian company that has long hosted the race, The Stronach Group, also known as 1/ST, is in the midst of an exit from Maryland racing, although it is running this year’s and next year’s Preakness Stakes.

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Maryland’s state government has invested over $500 million into infrastructure aimed to provide a lifeline to the industry, but it remains sidelined from Preakness Day. Until a state-created nonprofit gets to operate and profit from the festivities in 2027, Maryland will settle for sponsoring a festival leading up to the race.

Due to renewed efforts from the city and state, there has been more visible Preakness promotion this year, with signage downtown and events this week, including D-Nice performing at Pier Six Pavilion on Wednesday.

Infield merriment on race day, however, will be slimmed down.

Two friends dance together in the rain at Infield Fest during Preakness at Pimlico on May 18, 2024.
Revelers dance in the rain at Infield Fest during the Preakness in 2024. (Kaitlin Newman/The Baltimore Banner)

Instead of revelers crowding a stage for a series of musical performances, which have included the likes of Bruno Mars in recent years, there will be a separate area for about 3,000 partygoers — still with access to bottomless booze — and a relocated stage for trackside shows. Grammy winners Wyclef Jean and T-Pain will perform, but instead of playing for the infield, they will face the Pimlico grandstand.

That marks a pivot from the past 15 years, when the infield featured traditional concerts. This layout “has never been done before at the Preakness,” 1/ST said in a press release.

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Then there’s the race itself.

The Kentucky Derby champion always, theoretically, has a shot at the Triple Crown, so the pursuit of racing’s most prominent prize really begins at Pimlico, according to Preakness loyalists.

But even that aspect is peculiar this year.

Jockey Junior Alvarado celebrates after riding Sovereignty to victory in the 151st running of the Kentucky Derby horse race at Churchill Downs Saturday, May 3, 2025, in Louisville, Ky.
Jockey Junior Alvarado celebrates after riding Sovereignty to victory in the 151st running of the Kentucky Derby at Churchill Downs on May 3. (Brynn Anderson/AP)

Derby champion Sovereignty is skipping the Preakness, a historic rarity that has become less surprising as the Triple Crown’s swift schedule gives trainers pause.

Instead of racing two short weeks after their thunderous Derby win, trainer Bill Mott will rest Sovereignty and point him toward the Belmont Stakes next month. It marks only the second time in the past four decades that a healthy Derby winner has skipped the Preakness — but both occasions have occurred in the past four years, illustrating a growing problem for the industry.

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Rich Strike, the 2022 Derby winner, rested until the Belmont. But that marked the first time since 1985 — when Spend a Buck’s owner was lured away from the Preakness with a record payday at a New Jersey track — that a healthy champ skipped.

The Triple Crown, achieved only twice since Affirmed in 1978, is elusive and captivating, but in recent years owners have hesitated to pursue the feat. Horses have fragile legs, and pushing them to the limit twice in two weeks can be dangerous.

Jockey Mike Smith reacts after guiding Justify to win the 150th running of the Belmont Stakes horse race and the Triple Crown, Saturday, June 9, 2018, in Elmont, N.Y.
Jockey Mike Smith rejoices after guiding Justify to win the Belmont Stakes and the Triple Crown in 2018. (Julio Cortez/AP)

1/ST previously pitched a change to the racing calendar, but the tradition has never been bucked.

So the 150th Preakness won’t feature perhaps the race’s biggest draw, the potential of a Triple Crown (Derby runner-up Journalism is the race favorite). But, before Sovereignty’s absence, organizers said ticket sales were going much better than in recent years.

Preakness attendance regularly surpassed 130,000 before the pandemic, but in the last few years, as 1/ST organizers said they sought a “reimagined” event, it has not exceeded 47,000.

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Rosenberg, the state legislator, first attended the Preakness more than 60 years ago.

He grew up in the area, and Henry Cooper, known for painting jockey portraits at Pimlico, was the cantor who taught him the Torah portion he read at his bar mitzvah — which took place on Preakness Day, 1963. Candy Spots, Rosenberg recalled, won that race.

Though this year is a culmination of decades of Preakness Days, Rosenberg has not noticed, among his friends, a certain enthusiasm for this year’s race. Instead, there’s more excitement for what’s to come — when the race, hopefully, returns to a new Pimlico in 2027.

As for how Rosenberg will feel exiting the original Pimlico today for the final time?

“That’ll depend on whether I have a winning ticket,” he said.