Crosby wore a protective mask while skating with injured teammates James Neal and Paul Martin.
Coach Dan Bylsma said there is no timetable for Crosby's return, but called it a positive step for the NHL's leading scorer.
"I would say a foot in the water," Bylsma said. "I didn't go out there and see how hard he did go, but I know he was just out for basically a skate. He got out there for a little bit of exercise and to get on the ice."
Crosby, whose 56 points are four ahead of Tampa Bay's Steven Stamkos and Martin St. Louis, has not played since being struck in the face by a puck on March 30. The Penguins have gone 4-2 without him and remain atop the Eastern Conference standings with two weeks left in the regular season.
Neal hasn't played since being diagnosed with a concussion following a hit from New York Rangers defenseman Michael Del Zotto on April 5. Bylsma called Neal "symptom-free" but added that the winger will not be rushed back.
"It's definitely good to see guys on the ice and skating," Bylsma said. "I think it bodes well for their situation."
Center Evgeni Malkin, who missed Saturday's 3-1 win over Florida with an upper body injury, could play Wednesday against Montreal.
The reigning NHL MVP is dealing with a lingering shoulder issue that can make it difficult for him to take a full shot without pain.
"I feel good," Malkin said. "We have a couple days off and skate today and I have little bit of injury, but we still have time until the next game."