The Mount of Olives was a place of comfort and support for Jesus. In Luke 22:39 it says, "And He came out and proceeded as was His custom to the Mount of Olives; and the disciples also followed Him." John 18:2 points out that "Judas also, who was betraying Him, knew the place; for Jesus had often met there with His disciples." I believe Jesus had a need for fellowship but additionally there was always an opportunity to teach! Jesus was taking His disciples into His darkest hour to let them see how He would face it!
The garden located on the Mount of Olives was indeed a place of sorrow. In Matthew 26:38, Jesus said His soul was experiencing sorrow to the point of death. The following is a quote from a sermon of John MacArthur's titled "Man of Sorrows".
"Our Lord began to experience deep anguish. Jesus didn't go to the cross and die and then rise again without feeling anything. Every omniscient thought that anticipated the cross repulsed Him. He agonized over the reality of the cross. He despised everything connected with it--guilt, sin, death, isolation, loneliness, and estrangement from God. He didn't take it on coolly and calmly, as if He were turning a page in a book on redemptive history; it brought Him indescribable agony. His horror of the cross so repulsed Him that it's beyond our understanding.
Yet our understanding of the magnitude of the love and sacrifice of Jesus Christ is enhanced by knowing this: each time Jesus thought about the cross, He died. His omniscience allowed Him to experience His own death. Because He fully understood everything, He fully experienced His death before it ever happened. Is there any wonder that He was "a man of sorrows, and acquainted with grief" (Isa. 53:3)? The pain of the cross was always with Him, but it was in the garden that it reached its apex. His victorious endurance of that pain shows how much He loved the Father and submitted to His will, and how much He loved sinners."
The Garden of Gethsemane was a place of solitude. In Matthew 26:39 it says that Jesus "fell on His face and prayed..." Charles Spurgeon has written "Be much in solitary prayer it is the key to open heaven so it is the key to shut hell." It was through prayer that Jesus was able to withstand the final temptations - for in that garden Satan and his demons were in a battle to stop the redemptive work of the cross! In Luke 22:45-46 we see Jesus comes to the disciples and "found them sleeping from sorrow, and said the them, 'Why are you sleeping? Get up and pray that you may not enter into temptation.'"
The garden was a place of struggle. In Matthew 26:39, "And He went a little beyond them, and fell on His face and prayed, saying, 'My Father, if it is possible, let this cup pass from Me; yet not as I will, but as You will.' " I love how in His greatest trial Jesus cries out My Father. Mark 14:36 tells us that He actually prayed Abba, Father which translated is a more intimate Daddy, Father. Charles Spurgeon has said that we should plead our adoption in the day of trial because nothing can forfeit a child's right to a fathers protection. Jesus was not asking to avoid the redemptive work. He's just asking if there's another way to accomplish it. If it is possible doesn't mean in the sense of power, but if it is possible in the sense of the plan.
The garden was a place of submission. In John 12:27 he said, "Now my soul has become troubled and what shall I say, father save me from this hour? But for this purpose I came to this hour." God am I asking you to deliver me from this hour of redemption? No, this is why I came, but is there any other way to do it? And then his response, wonderful response, the response that of course you knew would be his, "Yet not as I will, but as thou wilt." There's the commitment. He came to do the father's will and if this was it, he would do it. He would never set aside the father's will. If there's no other way, I'll do it. Complete and perfect obedience. At this very point Luke 22:44 tells us he began to sweat great drops of blood.
Finally, the garden was a place of strength. We can see that Jesus has been strengthened in Matthew 26:46 "Get up, let us be going; behold, the one who betrays Me is at hand!" Jesus had gone into the garden very sorrowful and now emerges strengthened. Before He finished His prayer, we know that the Father sent a heavenly messenger to His Son. Luke 22:43 says, "Now an angel from Heaven appeared to Him, strengthening Him." In verse 47 we see that Jesus was strong in the face of Judas' betrayal, in verse 51, He was strong in Peter's attack on the servant of the High Priest and in verse 56, He was strong in the face of His arrest.
The following are the words of Max Lucado from his book, "When Angels Were Silent":
The battle is won. You may have thought it was won on Golgotha. It wasn't. You may have thought the sign of victory is the empty tomb. It isn't. The final battle was won in Gethsemane. And the sign of conquest is Jesus at peace in the Olive trees. For it was in the Garden that He made His decision He would rather go to hell for you than go to heaven without you.
There are two things that I want to always remember about my time in the Garden of Gethsemane. One is that when Jesus faced temptation He was able to stand firm through His knowledge of scripture and through prayer! The other truth that I don't ever want to forget is that when He was in the garden He knew my name! It had already been written in the Lamb's Book of Life and the cup that He would drink would include my past, present, and future sins! May my gratitude for His sacrifice demonstrate itself in the way that I live, the way that I speak, and the way that I think!
For our sake He made Him to be sin who knew no sin, so that in Him we might become the righteousness of God.