Isaiah 5 – The Vineyard Song and Six Woes of Judgment
Isaiah Chapter 5 opens with a poetic parable—a love song from God to His vineyard, Israel. Despite divine care, the vineyard produced wild grapes. The tone shifts dramatically as Isaiah pronounces six woes over Judah, condemning greed, injustice, drunkenness, and spiritual blindness. The chapter climaxes with the warning of foreign invasion as God lifts His protection.
Cared For, Yet Corrupt
✔ God lovingly prepared His people to bear fruit.
✔ Rebellion turned beauty into barrenness.
✔ Sin has consequences—national and personal.
✔ Woe follows when truth is rejected.
✔ Judgment will come like a roaring army.
📖 Isaiah 5:4 – “What could have been done more to my vineyard, that I have not done in it?”
🔎 God did not fail His people—they failed to respond.
Isaiah Chapter 5 - Overview
Isaiah 5:1–7 – The Parable of the Vineyard
📖 Isaiah 5:1–2 – “Now will I sing to my wellbeloved a song of my beloved touching his vineyard. My wellbeloved hath a vineyard in a very fruitful hill: And he fenced it, and gathered out the stones thereof, and planted it with the choicest vine…”
🔎 This poetic imagery portrays God’s loving investment in Israel. The “fruitful hill” reflects privilege and preparation. Yet the vine, though chosen and protected, produced wild grapes—corrupt fruit, symbolic of rebellion and sin.
📖 Isaiah 5:3–4 – “O inhabitants of Jerusalem… judge, I pray you, betwixt me and my vineyard. What could have been done more…?”
🔎 God appeals to the people’s logic: What more could He have done? This is a courtroom scene where He invites the audience to acknowledge that judgment is just. His care was complete—the failure lies in the response.
📖 Isaiah 5:5–6 – “I will take away the hedge… break down the wall… it shall not be pruned…”
🔎 Without God’s protection, chaos reigns. The “hedge” and “wall” symbolize divine restraint. When that is lifted, the vineyard (nation) is exposed to judgment, desolation, and ruin. The soil once tilled in grace becomes overgrown in judgment.
📖 Isaiah 5:7 – “He looked for judgment, but behold oppression; for righteousness, but behold a cry.”
🔎 Instead of justice, God found cruelty. Instead of righteousness, He heard the cries of the oppressed. The failure is not agricultural—it is moral. A nation planted for holiness has produced suffering.
➡️ God expects justice from those He’s planted in grace. When fruit is replaced by rot, pruning becomes necessary.
Isaiah 5:8–30 – The Six Woes
📖 Woe #1 – Isaiah 5:8–10 – “Woe unto them that join house to house… till there be no place…”
🔎 God condemns greed that monopolizes land and pushes out the poor. In response, He declares desolation: ten acres will yield little, and mansions will be left empty.
📖 Woe #2 – Isaiah 5:11–12 – “Woe unto them that rise up early… to follow strong drink…”
🔎 Pleasure has become priority. Alcohol and entertainment dull the senses. This lifestyle leads people to ignore the work and warnings of the Lord.
📖 Woe #3 – Isaiah 5:18–19 – “Woe unto them that draw iniquity with cords of vanity…”
🔎 Sin is pulled close like a prize. These people mock God and challenge His justice, saying, “Let Him make speed…”—a dangerous defiance.
📖 Woe #4 – Isaiah 5:20 – “Woe unto them that call evil good, and good evil…”
🔎 Moral confusion reigns. Darkness is paraded as light. This inversion corrupts society’s foundation and silences truth.
📖 Woe #5 – Isaiah 5:21 – “Woe unto them that are wise in their own eyes…”
🔎 Arrogance replaces dependence. Self-wisdom exalts man and rejects divine counsel.
📖 Woe #6 – Isaiah 5:22–23 – “Woe unto them that are mighty to drink wine… which justify the wicked for reward…”
🔎 Corruption taints the justice system. Bribes rule the courts. Power is used to protect evil, not righteousness.
📖 Isaiah 5:24–25 – “As the fire devoureth the stubble… because they have cast away the law of the Lord…”
🔎 Rejecting God’s Word leads to swift destruction. Fire is both image and reality—judgment will burn through all that is false.
📖 Isaiah 5:26–30 – “He will lift up an ensign to the nations from far…”
🔎 God will summon foreign nations as His tool of discipline. The imagery is terrifying: swift, unrelenting, and inescapable. When the Lord stretches out His hand, none can hinder.
➡️ These six woes unveil a nation in spiritual freefall. When people celebrate sin and mock righteousness, judgment is not only fair—it is inevitable.
Isaiah Chapter 5 - Deeper Study
Overview: Fruitless Vineyard, Faithless People
🔹 Timeframe: Pre-exilic Judah.
🔹 Setting: A land blessed yet corrupted.
🔹 Theme: Rebellion against God’s goodness.
🔹 Connection to Christ: Jesus repeats the vineyard parable in Matthew 21:33–44, pointing to Himself as the rejected Son.
When Grace Is Despised
This chapter shows that God’s care is not passive—He expects fruit. Judgment is not rushed—it’s earned by repeated refusal.
🔹 Blessings can become curses when abused.
🔹 Moral decay begins with spiritual neglect.
🔹 When truth is mocked, justice falls.
🔹 God’s patience has limits.
🔹 Judgment may be delayed—but never denied.
➡️ Do not confuse grace with permission. God planted you to bear fruit.
Key Takeaways
🔑 God gave every advantage—but His people rebelled.
🔑 Fruitless religion brings divine rebuke.
🔑 Each woe unmasks a symptom of a sick society.
🔑 Mocking God’s truth invites destruction.
🔑 Judgment comes when grace is exhausted.
Prophetic Patterns & Dual Fulfillment
🔮 Parable of the vineyard fulfilled in Matthew 21:33–44.
🔮 Six woes mirror later woes in Matthew 23 and Revelation 18.
🔮 Isaiah’s warning of foreign armies fulfilled in Babylonian conquest.
🔮 Fire as judgment imagery found in Hebrews 10:27.
Historical & Cultural Context
📜 Judah was expanding wealth, land, and leisure.
📜 Injustice and corruption grew unchecked.
📜 Prophets were ignored; sin was celebrated.
📜 God’s Word was sidelined in favor of pleasure.
Present-Day Reflection: The Modern Mirror
Like ancient Judah, today’s world boasts of progress while ignoring the God who blesses. We accumulate without compassion. We drink without discernment. Sin is paraded; truth is persecuted.
🔹 Wealth is worshiped more than wisdom.
🔹 Entertainment numbs repentance.
🔹 Culture calls evil good and truth hate.
🔹 Pride and pleasure eclipse holiness.
🔹 The warning signs are flashing—but few are watching.
➡️ When the vineyard turns wild, judgment ripens fast. Now is the time to return to the Vinedresser.
💡 Final Reflection: Called to Bear Fruit
Isaiah 5 reveals the heartbreak of rejected grace. God loved, planted, and protected—but found only rebellion. The six woes are not random—they expose a sick society rotting from within. The warnings aren’t just ancient—they’re alarmingly modern. And yet, even now, the call to repentance stands.
📌 Are you bearing fruit or resisting the Vinedresser?
📌 What warning signs are you ignoring in your own walk?
📌 Will you respond now—or wait until the hedge is removed?
📖 Isaiah 5:4 – “What could have been done more to my vineyard…?”
🔥 Fruitlessness invites fire—but faithfulness draws favor. Return to the One who planted you.
The Vineyard of the Lord Destroyed
Isa 5:1 Now will I sing to my wellbeloved a song of my beloved touching his vineyard. My wellbeloved hath a vineyard in a very fruitful hill:
Isa 5:2 And he fenced it, and gathered out the stones thereof, and planted it with the choicest vine, and built a tower in the midst of it, and also made a winepress therein: and he looked that it should bring forth grapes, and it brought forth wild grapes.
Isa 5:3 And now, O inhabitants of Jerusalem, and men of Judah, judge, I pray you, betwixt me and my vineyard.
Isa 5:4 What could have been done more to my vineyard, that I have not done in it? wherefore, when I looked that it should bring forth grapes, brought it forth wild grapes?
Isa 5:5 And now go to; I will tell you what I will do to my vineyard: I will take away the hedge thereof, and it shall be eaten up; and break down the wall thereof, and it shall be trodden down:
Isa 5:6 And I will lay it waste: it shall not be pruned, nor digged; but there shall come up briers and thorns: I will also command the clouds that they rain no rain upon it.
Isa 5:7 For the vineyard of the LORD of hosts is the house of Israel, and the men of Judah his pleasant plant: and he looked for judgment, but behold oppression; for righteousness, but behold a cry.
Woe to the Wicked
Isa 5:8 Woe unto them that join house to house, that lay field to field, till there be no place, that they may be placed alone in the midst of the earth!
Isa 5:9 In mine ears said the LORD of hosts, Of a truth many houses shall be desolate, even great and fair, without inhabitant.
Isa 5:10 Yea, ten acres of vineyard shall yield one bath, and the seed of an homer shall yield an ephah.
Isa 5:11 Woe unto them that rise up early in the morning, that they may follow strong drink; that continue until night, till wine inflame them!
Isa 5:12 And the harp, and the viol, the tabret, and pipe, and wine, are in their feasts: but they regard not the work of the LORD, neither consider the operation of his hands.
Isa 5:13 Therefore my people are gone into captivity, because they have no knowledge: and their honourable men are famished, and their multitude dried up with thirst.
Isa 5:14 Therefore hell hath enlarged herself, and opened her mouth without measure: and their glory, and their multitude, and their pomp, and he that rejoiceth, shall descend into it.
Isa 5:15 And the mean man shall be brought down, and the mighty man shall be humbled, and the eyes of the lofty shall be humbled:
Isa 5:16 But the LORD of hosts shall be exalted in judgment, and God that is holy shall be sanctified in righteousness.
Isa 5:17 Then shall the lambs feed after their manner, and the waste places of the fat ones shall strangers eat.
Isa 5:18 Woe unto them that draw iniquity with cords of vanity, and sin as it were with a cart rope:
Isa 5:19 That say, Let him make speed, and hasten his work, that we may see it: and let the counsel of the Holy One of Israel draw nigh and come, that we may know it!
Isa 5:20 Woe unto them that call evil good, and good evil; that put darkness for light, and light for darkness; that put bitter for sweet, and sweet for bitter!
Isa 5:21 Woe unto them that are wise in their own eyes, and prudent in their own sight!
Isa 5:22 Woe unto them that are mighty to drink wine, and men of strength to mingle strong drink:
Isa 5:23 Which justify the wicked for reward, and take away the righteousness of the righteous from him!
Isa 5:24 Therefore as the fire devoureth the stubble, and the flame consumeth the chaff, so their root shall be as rottenness, and their blossom shall go up as dust: because they have cast away the law of the LORD of hosts, and despised the word of the Holy One of Israel.
Isa 5:25 Therefore is the anger of the LORD kindled against his people, and he hath stretched forth his hand against them, and hath smitten them: and the hills did tremble, and their carcases were torn in the midst of the streets. For all this his anger is not turned away, but his hand is stretched out still.
Isa 5:26 And he will lift up an ensign to the nations from far, and will hiss unto them from the end of the earth: and, behold, they shall come with speed swiftly:
Isa 5:27 None shall be weary nor stumble among them; none shall slumber nor sleep; neither shall the girdle of their loins be loosed, nor the latchet of their shoes be broken:
Isa 5:28 Whose arrows are sharp, and all their bows bent, their horses’ hoofs shall be counted like flint, and their wheels like a whirlwind:
Isa 5:29 Their roaring shall be like a lion, they shall roar like young lions: yea, they shall roar, and lay hold of the prey, and shall carry it away safe, and none shall deliver it.
Isa 5:30 And in that day they shall roar against them like the roaring of the sea: and if one look unto the land, behold darkness and sorrow, and the light is darkened in the heavens thereof.
Date Written
740–700 BC
Written By
The prophet Isaiah, son of Amoz
Language
Hebrew
Verses
30