I saw there was a beach concert today and just bit the bullet and went for it. Such short notice none of my friends were available so I went alone. It was awkward and I didn't talk to many people only staff, but I enjoyed some music, got out the house and met some cool people.
All in all it was good and definitely possible to do for anyone on the fence. Especially if it's with people in your age bracket (this one wasn't it was mainly people way older). It's daunting and takes a self kick to do it but you can. If you want to talk to someone there go ahead talk about the event or music, especially at an event with drinks people are pretty open to talk and if it goes wrong, they won't remember you by the next day.
It's definitely optimal to go with friends but you can go it alone and enjoy yourself. Good luck out there whoever reads this.