Rustic Lodge Stair Railing
I always drilled my holes after the rail was installed, there is way too much room for error to drill on a drill press, not to mention getting the angle correct, even if you could figure out how to handle the long rail on a drill press. You wouldn't be able to drill the bottom holes, on your stairs, with a drill press anyway.
Lay out where the bottom holes will be drilled, then plumb up, mark the spot where you will drill the top holes. If it will help you, there are drills with a leveling bubble in the handle but it never helped me much.
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