In the game, the player can explore and play in an interactive schoolhouse which contains many activities in the classroom. The player is rewarded with train tickets for completing activities. When the player collects four train tickets, they can go on a magical train ride to one of ten different locations. After visiting a location, the player gets a stamp in their passport book.
- Blocks - Help Kisha sort her blocks and put them away. The blocks come in different sizes, shapes, and colors. Click and drag the blocks into the buckets that they belong in.
- Connect the Dots Book - Connect the dots to make a picture. You can choose to play connect-the-dots with either numbers or letters. You have to click on the dots in either numerical or alphabetical order.
- Kitchen - Help Pierre bake tasty foods. Pierre will ask you for a certain food. Click on the food that he asks for and put it in the pot.
- Toy Box - Help pick up the toys and put them away. Eleanor, Pierre, and Kisha will each say a word. Find the toy with the same beginning sound as those three words. Click on it to pick it up, then move the cursor over the toy box and click again to put it away.
- Player Piano - Choose a song to listen to and sing along with. Pick a scroll to play a song. There are five songs: "London Bridge", "Old MacDonald", "This Old Man", "Twinkle, Twinkle, Little Star", and "I've Been Working on the Railroad". The song lyrics will appear on the screen, and the characters will clap or dance. You can also play your own song by clicking on the piano keys.
- Bird Nests - Help the mommy bird feed her hungry babies. Kisha will hold up a picture with worms on it, and say out loud how many worms there are. Click on the nest with the same number of birds.
- Easel - Find hidden letters, numbers, or shapes in Kisha's paintings. Click on the buckets to change to shapes, numbers, or letters. Kisha will specify what you should look for. The hidden shapes, letters, and numbers will be transparent with faint visible outlines. If you move your mouse over one, it starts blinking red. Click on all of the shapes, letters, or numbers that Kisha asked for.
- Mouse Hole - Play hide and seek with Cecil. First you have to turn off the light. Cecil will have hidden behind an object. He'll give you a clue as to where he is hiding. Click on the object you think he is hiding behind.
- Mix and Match Book - Pierre will put on a costume. His book has various clothes in it. Flip to the pages that have the same clothes that Pierre is wearing.
- Wagon and Balls - Casey, Pierre, and Eleanor stand in three different lanes. They will roll different colored balls towards you. You will be instructed to only catch balls of a certain color. Move your wagon back and forth to catch balls. Move your wagon out of the way of balls of the wrong color.
- Magical Train Ride - Once you have four tickets, you go the station. Click on one of ten tunnel entrances to go to a location. The locations are: The Animal Kingdom, Calendarville, Color World, The Land of Many Seasons, The Land of Numbers, Letter Island, The Musical Notes Land, Ruler Land, Shape Land, and The Stars and Moon. When you go to a location, you get to see a short musical video clip.
In this game, the Toolbar is represented by nine toy blocks. The Toolbar has the following features (from left to right):
- Back/Exit - During an activity, this button allows you leave the game and return to the classroom. When you are inside the classroom, this button allows you to exit the program.
- Help - Clicking this button will give the player tips on how to play the game.
- Level Bars - This button allows the player to adjust the difficulty levels of each activity.
- Tutor Mode/Progress Report - This button allows the player to access the tutor mode, or view their progress report.
- Passport Book - This button allows the player to view all of the stamps they have collected.
- Train Tickets - The last four blocks display the Train Tickets that the player has earned.
- JumpStart Preschool Theme Song
- The Animal Kingdom
- Color World
- The Land of Many Seasons
- The Land of Numbers
- Letter Island
- The Musical Notes Land
- Ruler Land
- Shape Land
- The Stars and Moon
- I've Been Working on the Railroad
- London Bridge
- Old MacDonald Had a Farm
- This Old Man
- Twinkle, Twinkle, Little Star
- The Days of the Week
- The Alphabet Song
- Numerical Order
- Alphabetical Order
- Listening Skills
- Similarities and Differences
In 2000, JumpStart Preschool was re-released as part of a Deluxe 2 CD Set. The game JumpStart Around the World was included with it.