The tour, unusual for Romney, marked an attempt to upend Obama's core argument against his challenger: that the Republican is disconnected from the ordinary folks he aims to lead.
The five-day, six-day excursion by bus—as well as airplane—comes after Romney spent the past few weeks courting wealthy donors and raising millions of dollars to fund his presidential ambitions.
"If there's ever been a president who has not given a fair shot to the middle-income Americans of this great nation, it is Barack Obama," Romney declared from a makeshift podium during an "ice cream social" in Milford's town square. "I understand what it takes to get people to work again. I will do that to help the American people from the richest to the poorest and everybody in between."
Obama used the power of the presidency to overshadow Romney's big day.
The president announced that the government will stop deporting hundreds of thousands of young illegal immigrants who were brought to the U.S. as children. Romney waited until late afternoon to address the issue although the news had been out since morning. When he did, he distanced himself from the sharp rhetoric he used during the primaries.
Romney once vowed to veto the so-called DREAM Act, stalled legislation once backed by Republicans and Democrats that would help some of those young immigrants become citizens.
Romney's response infuriated some New Hampshire conservatives and underscored his delicate standing in the party following a divisive GOP primary, even as he seeks to broaden his appeal.
"Romney's got to stop pussyfooting around this," Rachel Swinford, a 59-year-old New Boston, N.H., jewelry maker, who backed Rick Santorum during the primaries. "We're stuck with Romney. But compared to Obama, I mean, what choice do we have?"
Romney also faces challenges in his attempt to appeal to the middle class and people in small-town America. The tour is aimed at a segment of America he has little direct experience with. The son of a governor, Romney has lived largely in upscale suburban settings and is worth as much as $250 million.
Democrats lashed out at Romney's message on multiple fronts, including in the skies above his two New Hampshire bus stops. One small plane towed a banner that said: "Romney's Every Millionaire Counts Tour," while another hired by the Romney campaign towed a competing message: "Romney for president - 2012."
A team of Democratic mayors also charged that the Republican's business career and term as Massachusetts governor was defined by efforts to help the wealthy at the expense of the middle class.
"This 'middle class under the bus tour' is going to give us a chance to highlight those differences," Los Angeles Mayor Antonio Villaraigosa told reporters during a conference call organized by the Obama campaign.
The bus tour— Romney planned to fly each night to the next state—is Romney's first traditional campaign swing aimed at undecided voters in six battleground states—New Hampshire, Pennsylvania, Ohio, Wisconsin, Michigan and Iowa—that Obama won in 2008 and that may decide the presidential election in November.
Speaking earlier Friday at the New Hampshire farm where he launched his campaign a year ago, Romney told supporters they don't have to "settle for these years of disappointment and decline." He promised a revived America.
Americans are "worried and anxious. They are tired of being tired. And they are tired of a detached and distant president who never seems to hear their voices," Romney said, as he stood on the bed of a farm's tractor trailer and read from a teleprompter.
He invoked the names of famous American writers and entrepreneurs like Mark Twain, John Steinbeck and Thomas Edison while lamenting the decline of Rust Belt cities like Detroit, Pittsburgh and Cleveland.
The tour will take Romney to places "off the beaten path," his campaign said, including at least 14 small cities and towns over the five days of the tour. It will bring Romney back to the kind of retail politicking he hasn't engaged in since the early days of the Republican primary, when he campaigned in diners and coffee shops across Iowa and New Hampshire.
With that opportunity, however, comes risk.
Romney sometimes ran into trouble in less scripted environments and the bus tour is bound to test him again. At one stop at a New Hampshire before the state's primary in January, a gay veteran confronted Romney about his opposition to gay marriage. Romney also has long faced questions about his ability to connect with the average people he meets.
Romney senior strategist Russ Schriefer suggested Romney has no problem connecting with voters. "I think if you look at the polls, they like him enough," he said.
A Gallup/USA Today poll conducted in early May found that 63 percent of voters said Obama was likable while 28 percent said the same about Romney. In another poll, most of those surveyed felt Obama better understood their problems.
Blake Williams, a 26-year-old automation engineer from nearby Saco, Maine, suggested that Romney's long career in business can make it difficult for him to connect with middle-class people. But he said that won't affect his vote.
"We need somebody to get the job done, not charm people," Williams said as he waited to shake Romney's hand at the farm.