Pictures of Hollis Woods is the story of an 11-year-old orphan girl (Hollis Woods) who has been moved to countless foster families unfolds through the pictures she draws. The one picture to another family again. This time however, Hollis refuses to leave Josie since she feels Josie needs her. She and Josie run away because Hollis wants to stay with Josie. She ends up returning to Branches, which is the summer home of the last family she ran away from (the Regans). The Regans were in their winter home so would never know Josie and Hollis were there. Hollis throughout the story still however longs to be with them again and misses them very much.
The Regans were an amazing family for her and she loved them all very much. Hollis(Holly) left the family because of her fear of her attachment and out of guilt. The Regans have a son named Steven who developed a close bond with Holly. One night while the Old man (Steven's father) and Izzy (Steven's mother) were out and Steven was fishing, Holly decided to leave the house and go up the mountain by the house. She ended up hurting herself because she got too close to the edge and rolled down the mountain a few feet. She needed Steven to find her to drive her down because of her injuries from the fall. He had to drive all the way up the mountain to get her and while he was on his way back down the mountain as careful as he was the truck ended up sliding because of the mud, which caused the truck to tip over to the side. The truck was sliding all the way down the mountain and it crashed.
The Old man and Izzy got her and Steven to the hospital. Hollis had stitches on her head from the car crash. When she was brought back home by Old man and Izzy, the guilt started to sink in. She kept thinking if she had not gone up the mountain then Steven would not have crashed the car. The guilt made her pack up her bags and run away once again from another family even though she loved them and they loved her.
While she is in Branches with Josie trying to hide from the "mustard woman", Hollis goes fishing. In the woods, she runs into someone who she cannot see very well. She assumes it is a fisherman and runs away from him. Josie and Hollis celebrate Christmas together in the Regans' summer house. Hollis gives her a drawing of Josie, Henry, and Beatrice (Josie's cousin) by the popcorn machine in the theater. Josie gives her the wooden self sculpture she promised she would make for Hollis. She also gave Hollis a tin of candies that she found in the house which were Izzy's. Josie said the candies were from Santa Claus.
Hollis soon begins to think Steven is in the area because she keeps seeing Steven's sweater in the house move and Josie claims she heard a snowmobile. She calls Beatrice to come and live with Josie so she can take care of Josie. Beatrice agrees to live with Josie. She hears the snowmobile and then she sees Steven and when she sees him she says to him "Steven Regan. Happy Birthday." Then, she goes back to living once again with the Regans and this time she has a baby sister in the family named Christina. She's content with her new and forever family.