Crawford was in Boston on Friday and is set to continue his Minor League rehab assignment on Saturday with Triple-A Pawtucket. The left fielder will move up a level from Double-A Portland, where he went 4-for-10 with a triple and an RBI in three games.
Boston hasn't said yet when the two outfielders will be activated, but the club's first series of the second half -- at St. Petersburg against the Rays -- could be a reasonable estimate.
Ellsbury, recovering from a separated right shoulder, is scheduled to play for Portland on Friday night in his second game with the Sea Dogs. On Wednesday, Ellsbury went 1-for-5 and played center field, with Crawford playing left.
"It was good to get back out there in the outfield with him, just to get the feel for that again," Crawford said. "Hopefully we can be playing together soon sometime. He looks pretty good. He got a couple of hits down there and ran down a few balls.
"It's one of those things you don't know until you get there. So I'm just taking it day for day right now -- that's how we're approaching it -- and we'll see. I'd like to get back whenever, as soon as possible, but we'll just have to wait and see."
Crawford is recovering from left wrist surgery and a UCL sprain in his left elbow. He said his elbow still causes discomfort, but not at the plate.
"It's not 100 percent healthy, but I'm able to hit, so I said pretty much whenever I'm able to start hitting the ball and swinging the bat, then I'll play," said Crawford, who has not played in the Majors this season.
With Minor League teams also taking time off during the All-Star break, Crawford and Ellsbury will lose out on valuable playing time.
"We're going to try to get them in games; I'm not sure where," said Red Sox manager Bobby Valentine. "There are not games during the All-Star break every day, so they'll play as often as the schedule allows them."
Outfielder Ryan Sweeney, out with left big toe inflammation, began a rehab assignment of his own on Thursday with Portland, going 1-for-4.
Scott Podsednik is the outfielder closest to returning to the Red Sox. He could be activated prior to Saturday's doubleheader against the Yankees, with Boston allowed to expand its active roster to 26 players for each of those games.
"He just got examined today, and he's healthy and ready to go," Valentine said of Podsednik. "We have the extra man for the first time in my life in dealing with that situation, so we're trying to figure out all those options that we might have, and of course he'd be one of them."