Is it possible to upgrade Apache Cassandra 2.1.9+ to Apache Cassandra 3.1+ directly?
The release notes for 3.0 mention direct upgrades need a minimum of Apache Cassandra
As per my experience about upgrading Cassandra if you are doing upgrade from below 2.1.9 then you must upgrade to 2.1.9 or above then you can directly upgrade to 3.x version. There is no issue in this way and you upgrade will be successful but if you are doing it on production make sure to do rolling upgrade with all prerequisites and backup. Don't forget to run nodetool upgradesstables after Cassandra upgrade.