A twist on the classic "Pin the Tail on the Donkey" game, this activity is sure to make your preschoolers giggle. Print a picture of Cupid onto large poster board or, if you are artistic, draw one yourself. Cut small bows or hearts out of smaller pieces of poster board and label each one with a child's name. Show your students where the bow or heart should go in relation to Cupid. Blindfold each of the children and spin them around one or two times. Line your preschoolers up so that they are facing the board and have them try to pin their bow onto Cupid. The player who comes closest to pinning the bow on the right spot wins a prize.
Take several pieces of colored construction paper and cut hearts out of them. Make sure they are large enough for your preschoolers to see, yet not so large that they find them right away. Have your preschoolers close their eyes while you hide the hearts around the classroom. Tell them that the person who finds the most colored hearts wins the game. Make sure you keep track of how many hearts you originally had so that you know if they are all accounted for at the end of the game.
You can also cut each heart in half, using a different pattern in the middle of the heart. The first one or two children who find matching broken hearts win prizes. Make sure the children understand that the hearts must be the same color and must match down the middle in order to complete the piece.
Purchase or make your own Bingo cards for your preschoolers with colored shapes instead of numbers and letters. Pass out small candy hearts or red hot cinnamon candy to use as playing pieces. Tell the children that you will call out a color and a shape. If they have that color and shape on their card, they should place a piece of candy on that square. If they get five pieces of candy in a row, they are to shout "Happy Valentine's Day!" Make sure you check the child's card and explain if they got a color or a shape incorrect. Give the winner a small prize or piece of candy.
Use duct tape or masking tape to mark a line across a portion of your classroom. Place three red buckets five or six feet away from the line. Give each student 10 or 15 small candy hearts and instruct students to try to toss them into the buckets. Make sure they stand with their toes behind the line as they play the game. You can either award a small prize to the child who gets the most candy hearts in or every time a candy heart is tossed successfully.
This game is like "Hot Potato" except it is played with a Valentine's Day teddy bear instead of a potato. Arrange your preschoolers in a circle on the floor and give one of them the bear. Turn on music and tell them to gently pass the bear around the circle. When the music stops playing, the child holding the bear is out. Give each player a small piece of candy for trying and let the winner leave with the plush teddy bear. Be careful, however, as this game can turn rowdy extremely quickly. You might have to remind the children not to throw the bear at each other.
Fill a large jar with chocolate kisses or pieces of candy. Ask each child to write his or her name on a piece of paper and a guess of how many pieces of candy are in the jar. The winner is the child who guesses the correct number or who comes the closest. Let the winner take home the jar of candy or award him a different prize and let the candy be split up among all of your preschoolers.