Barack Obama gave 20 of his local supporters the surprise of their lives Tuesday night showing up at a Billings home. Then got personal with nearly 200 Montana military families. And as his familiarity with the state grows, some say so does his support.

"Obama is increasingly starting to do more of these, less scripted more casual no teleprompter and in terms of the audience it worked well, and he certainly knows his stuff," says MSUB Political Analyst Craig Wilson. This stop hoped to gain support from Montana's military families, the state has among the highest population of veterans per capita in the country.

Obama also aims to reach Montana's middle and working class families. "He's a player and he's going to run his campaign here. He's got a lot of players in Montana, and he's not going to give up," says Wilson.

But after five stops in a red state, with only three electoral votes, some ask, why Montana? Wilson says the race could be that close and McCain's absence in Big Sky country could give Obama the upper hand. “I think the Republicans will be making a mistake if they, for whatever reason, can't get him in here. Because it matters to voters in Montana and that he cares enough to come."

Still, he says McCain leads Obama in Montana by 6 points, which means even 5 stops may not be enough. "He's not over the hump; he's doing well now, but I'd still have to say that McCain is probably the favorite here, but it doesn't mean Obama can't win in Montana, he could win in Montana." Said Wilson.

Wilson says while Wednesday's stop helped Obama with veterans and military families he must still make up some ground with the state's agricultural community.