The Globe of the Great Southwest - The globe theater is a replica of Shakespeare's globe theatre. They put on many plays here and they also host a Shakespeare festival every year. For more info click here.
The Permian Playhouse - They put on a variety of plays and musicals throughout the year. Many years ago I saw Fiddler on the Roof here and it was very good. Click here for more info.
The Commemorative Air Force museum - includes planes from several foreign countries and other military conflicts since World War II. They host an air show every year. For more info click here.
Midland Rockhounds - They are the areas minor league baseball team. The games are very fun and kid friendly. They have a very nice playground for the kids. They do a great fireworks show for the 4th of July. For more info click here.
Odessa Jackalopes - They are the area's minor league hockey team. The games are kid friendly and fun. For more info click here.
Go golfing there are several courese in the area.
Ratliff Ranch Golf Links