Winters is an island country in the region of Foggyland in EarthBound. It is home to many important characters and locations in the game, including Jeff Andonuts, Tony, Maxwell Labs, Tessie, Bubble Monkey, Brick Road, the Tessie-Watching Club, and Dr. Andonuts. It is also home to the Ness's fourth Your Sanctuary location, Rainy Circle, and the Stonehenge Base located directly under Stonehenge. The concept of this area is mainly based on England, Scotland and Canada.
Winters is first introduced after Ness and Paula find themselves trapped under Threed's graveyard. Paula resorts to calling Jeff via telepathy, asking for help. Jeff is awoken at night in the Snow Wood Boarding School, and with the help from his friend Tony and an older student named Maxwell Labs, Jeff leaves the boarding school and heads south to Lake Tess. After purchasing a peculiar bubble-blowing monkey from the Best Friend Drugstore and staying the night with the Tessie-Watching Club, Jeff and the Bubble Monkey arrive at the lake. With the help of Bubble Monkey, the mythical sea monster Tessie emerges from the water and carries the two across the lake on her back. After arriving on the other side of the lake, Jeff and Bubble Monkey work their way through Brick Road's dungeon and Rainy Circle dungeon, arriving in Stonehenge. Then, Bubble Monkey encounters a female monkey and leaves with her on a date. Jeff then arrives at the laboratory of his father, Dr. Andonuts, and is sent off on a flying device, the Sky Runner to rescue Ness and Paula in Threed.
Ness and Jeff can optionally return to Winters after Ness learns Teleport from monkeys in the Dusty Dunes Desert, however, it is not possible to cross Lake Tess and access the Stonehenge area, as Bubble Monkey is absent.
Shortly after Ness learns Teleport, the three party members leave Eagleland on a repaired Sky Runner back to Dr. Andonuts lab in Stonehenge. There, Ness is advised by Dr. Andonuts to investigate Rainy Circle while he reprograms the Sky Runner to fly to Summers. The three head to Rainy Circle Dungeon to defeat Shrooom!, and then Ness absorbs the power of Rainy Circle. Afterwards, the party heads back through Stonehenge and rides the reprogrammed Sky Runner to Summers.
Later in the game, Dr. Andonuts, Apple Kid, Tony, and others are kidnapped by Giygas's forces. Ness, Paula, Jeff, and Poo teleport to Winters to rescue them, only to find that the area is swarming with powerful monsters. Bubble Monkey helps them cross Lake Tess again, and the four work their way to the secret base under Stonehenge. At the entrance, Ness uses Apple Kid's last invention, the Eraser Eraser , to remove the Iron Eraser and gain access to the bulk of the base. After struggling through the base, they encounter the kidnapped humans, encased in fluid-filled glass tubes. In the next room lies the Starman DX. After defeating him, the kidnapped humans are saved, and the Ness and co. leave Winters for the final story-related time.
In the Mother 1+2 Art Book, several pictures of Winters were included that showed radical differences to the area.
- Lake Tess, the Tessie-Watching Club and Tessie's way of letting Jeff ride it were significantly different.
- Winters was originally going to have a small village.
- Stonehenge was simplified, and Jeff appeared to have a differently colored Bicycle.
- Dr. Andonuts and his laboratory had many more features, including a rocket ship nearby.