Can a 2008 Harley street glide pull trailer?

Yes. The Harley-Davidson Street Glide is a heavy motorcycle that is capable of pulling a trailer. The manufacturer's recommended towing capacity for the Street Glide is 1,500 pounds, which is enough to pull a small to medium-sized trailer. However, it's important to note that the towing capacity may be reduced depending on the specific model and year of the Street Glide, and other factors such as the weight of the motorcycle, the terrain, and the weather conditions.