Principal photography began in Van Nuys, California, where Smith first put the story of Wish You Were Here on paper. "We gave everything in Los Angeles a very blah, artificial, sickly brown and yellow kind of feel to it, mirroring the characters' view of the superficial, ugly people they know there. It's a miserable experience for them. It's not until the boys finally get out of there and onto the highway that we see things lit naturally, with more color, more vigor and life and rightness to it."
The "Core Team" then made the actual cross-country journey - Director Jason Smith, Assistant Director Brian Hodges, and Actors Bob Canning, Bill Kingsbury and Steve Sabellico. The team traveled from Los Angeles to Dallas, took a left, drove to Chicago, took a right, and drove to western Massachusetts. They shot on the road as they went, stopping at destinations planned for in the script. Cast and crew spent the night under the stars in Joshua Tree National Park, crowded into a single room in a tiny Oklahoma motel, and bargained for floor space while staying with friends and family across the USA. The whole trip took eight days.
They were joined in Illinois by actors Andria Brown and Kirsten Gronfield, and then by the rest of the cast and crew in Franklin County, Massachusetts.
The town of Greenfield was base camp for the second half of the shoot. The team spent the next nine days shooting interiors there and throughout the rest of Franklin County. Cast and crew stayed with Kingsbury's extended family quite literally in the middle of the woods, sleeping in tents and trailers donated by local friends and relatives, and in a 34-foot camper loaned to the production by a local dealer.