When the prophets spoke of the coming glory of God's Kingdom, ushered in by the Messianic King, it seems that wine is common image:
On this mountain the Lord of hosts will make for all peoples a feast of rich food, a feast of well-aged wine, of rich food full of marrow, of aged wine well refined. (Isaiah 25:6)
They shall come and sing aloud on the height of Zion, and they shall be radiant over the goodness of the Lord, over the grain, the wine, and the oil, and over the young of the flock and the herd; (Jeremiah 31:12)
“And in that day the mountains shall drip sweet wine, and the hills shall flow with milk," (Joel 3:18)
“Behold, the days are coming,” declares the Lord, “when the plowman shall overtake the reaper and the treader of grapes him who sows the seed; the mountains shall drip sweet wine, and all the hills shall flow with it. "(Amos 9:13)
"Then Ephraim shall become like a mighty warrior, and their hearts shall be glad as with wine. Their children shall see it and be glad; their hearts shall rejoice in the Lord." (Zechariah 10:7).
Then Jesus shows up, and the very first thing He does to manifest His glory (John 2:11) is turn 150 gallons of water into the best wine anyone has ever tasted.
Coincidence? It seems like with His first miracle, Jesus wants to show the world that He is the Lord of the Feast.
Jesus was most surely "a man of sorrows, and acquainted with grief". In a culture of hedonism, we'd do well to remember that often. But likewise, it's worthwhile to remember that Jesus became a man of sorrows in order to prepare the greatest feast we've ever dreamed of.
Following Him is not gloomy.