Glossop Labour Club has a tunes session every Friday night:

http://www.glossoplabourclub.org.uk/activities.html

The Globe on High Street West does great (and very cheap) veggie food and wonderful beer:

http://www.theglobeglossop.co.uk

Glossop usually has some music going on somewhere most nights of the week:

https://www.whatsoninglossop.com/ecategory/music/

I love Glossop!

Harry