I believe this place is often overlooked by travelers and locals alike. It's a shame for such a place with quite an intriguing past and quite an interesting present. Before WWII this used to be the city casino (check out what it used to look like at the Stara Sofia blog).
Don't get me wrong. It was not a gambler's paradise but more like the most famous place for meetings and social networking. The biggest halls in town hosted balls, political meetings, concerts, even painting exhibitions. The casino was heavily damaged after the war and converted into gallery soon after.
Nowadays its big halls host exhibitions once again. The gallery has a huge collection - 3,500 paintings, 800 sculptures, 2,800 other drawings - but most of it is in storage. Usually there are at least two exhibitions in the gallery. They organize around 30 exhibitions every year.
Entrance is just ~1 EUR and free on Thursday. It's located in the park so it's the perfect place to enjoy a nice day outside.
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