Rolling your lawn is the process of dragging a heavy weight across your lawn to smooth it. While this may seem like a good idea, you should know that lawn rolling should only be done under certain circumstances and then with appropriate caution. Rolling your lawn improperly can do more harm than good. The heavy weight can compact the soil, making it difficult for roots to grow and spread. It can also make it more difficult for water to penetrate the soil. Instead, the water just runs over the top of the soil, carrying fertilizer and lawn food away from the lawn and into the sewer or septic system.
The only times when lawn rolling might be required are right after seeding or sodding a new lawn, in the winter if fluctuating weather caused the lawn to heave, and if your lawn is full of mounds and burrows from burrowing animals.
Rolling your lawn when the soil is wet will cause serious soil compaction, making it difficult for the soil to get the water and air it needs. Conversely, if the lawn is rolled while dry, the seeds will not come into contact with the soil as they should. Always roll your lawn when the soil is damp but not wet.
You don't need a heavy roller to roll your lawn. A light one will work just as well without heavily compacting the soil.
Only roll your lawn in the spring when the grass first comes out of dormancy and the roots are back in active growth.
Roll your lawn as infrequently as is necessary. There is no need to roll it annually, and this will only lead to heavy soil compaction. Try to limit the times you aerate to the situations listed above. Rolling your lawn just for appearance sake will backfire in the long run.
Instead of rolling your lawn, you might want to consider aerating it instead. Or at the very least, aerate it in the fall before you plan to roll in the spring. To aerate, you remove plugs from the soil with an aerator. This will leave your yard looking odd, but it will provide an avenue for water and air to circulate among your lawn's roots. The holes will eventually collapse in on themselves, after the roots have had a chance to get some air and nutrients. Don't aerate more than every other year and only do so at the end of the year.
The following spring, after the aeration, sprinkle new seed on the lawn to fill in any bare spots. Follow this with a good lawn starter fertilizer. Then using a light roller, roll your yard, gently.