From what I know it was celebrated during his time but I know little about how it was celebrated or its significance then. cheers
Shavout was celebrated at the time Christ was on Earth so growing up as a Jew He most definitely would have celebrated it.
Additionally, in Acts chapter 2 we see His disciples receiving the Holy Spirit and preaching mightily on the first Shavout after Jesus' resurrection and return to Heaven. So it seems like they were very aware of its importance to Jewish culture as well.
As for how it was celebrated, Jews from all over the Middle East and the Mediterranean came to Jerusalem for a feast. For more details on the specifics of the feast see Exodus 23.
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