The blue-chip stocks index quickly blew through the much-anticipated milestone in the opening seconds of trading, culminating a US rally in the wake of US President Donald Trump's election, in anticipation he will produce pro-growth policies.
About 15 minutes into trading, the Dow was 20 010.71 points, up 0.5%.
The broad-based S&P 500 also rose 0.5% to 2 290.43, while the tech-rich Nasdaq Composite Index gained 0.6% to 5 635.10.
The S&P 500 and the Nasdaq each closed at all-time records on Tuesday.
In crossing the 20 000 threshold after many failed tries, the market regained its optimistic mindset after the rally spurred by Trump's election stalled in mid-December and up to the January 20 inauguration.
Analysts said the shift was triggered by Trump's announcements on Tuesday to advance two major pipeline projects that had been blocked by former president Barack Obama.
The pipeline move "wasn't a surprise as it was consistent with campaign rhetoric, yet it was a timely reminder for a listless market of the Trump Administration's push to increase economic activity in the US," said Briefing.com analyst Patrick O'Hare.
The rally spurred more stock buying by investors who were caught off guard in what O'Hare dubbed "FOMO" or the "fear of missing out."
The renewed market confidence suggests investors are shrugging off worries about Trump, which include fears he will ignite a trade war with protectionist policies and push hard on controversial social policies.
Trump was expected later on Wednesday to announce the first steps towards building a massive wall on the Mexican border, a campaign promise that pleased his political base but has been criticised by others as unnecessary and mean-spirited, as well as a misuse of funds.
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