Play Chesterland Adventure Online

You play as Chester, this chubby-cheeked kid bouncing through crayon-colored levels, stomping walking apples and getting stuck on bizarre puzzles like a talking mailbox. It’s got that janky early-DOS charm—weird enemy patterns, slightly unfair jumps, and music that somehow worms its way into your head.

File size: 22.03 KB

Game Overview

Ever boot up an old MS-DOS game and immediately feel like you’ve been teleported back to 1993? That’s Chesterland Adventure for you—a weird little platformer where you play as this round-cheeked kid named Chester, bouncing through levels that look like they were colored in with crayons. The first time I played, I got stuck for way too long on a puzzle involving a talking mailbox (don’t ask), but that’s part of the charm.

It’s got that janky-but-lovable feel of early PC games—enemies move in weird patterns, some jumps are just slightly unfair, and half the fun is figuring out what the heck you’re even supposed to do next. But the colors pop, the music’s weirdly catchy, and there’s something about stomping on giant walking apples that never gets old. If you miss the days when games didn’t hold your hand and just let you wander into chaos, this one’s a time capsule worth opening.

Each game uses different controls, most DOS games use the keyboard arrows. Some will use the mouse , "Alt" ,"Enter" and "Space bar".