Tom Sawyer didn't have stain to whitewash his fence, but if he did, he might not have minded doing it himself. If you have a wood fence needing a facelift, consider staining instead of painting to give it a new lease on life. The bonus is that the stain protects the wood from moisture, splitting and warping while improving its appearance. For a fence facelift, a semi-transparent, water-repellent penetrating stain that colors the wood is a good choice.
A painting contractor will charge $794, including labor and to stain both sides of a 50-foot wood fence. You can do the job for $245, the cost of the stain, and save 69%. You can apply the paint with a sprayer, brush or roller. A paint sprayer is a good choice if there are no buildings or structures nearby that will require masking. If it's windy, spraying is not a good idea; and while spraying is fast, it uses about 25% more material than a brush or roller.
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You can take Tom Sawyer's approach and use a brush, but a roller and brush combination is a better bet. Use the brush to apply stain on the sides of the fence boards and a roller for the large, flat surfaces. However you apply it, make sure the stain penetrates the wood so it can protect the surface. Use drop cloths to protect the soil and plantings surrounding the fence.
Before staining a fence, use a garden hose or pressure washer to clean the surface and remove any dried-on dirt. If there are patches of dirt or mildew, remove them and let the surface dry thoroughly before applying the stain.