Sometimes, in our small woodworking shops we need to come up with how to drill into the head of wood strips. For example to make joints with dowels. Clamping the strips with a clamp and drilling the holes with a handheld drill does not usually give the best result. And to do it on the drill press, it might not seem possible. But actually it is.
As we will see in this post, we can rotate the head of our drill press and put its metallic table vertically in a way that allows to install a vertical plywood table, a vertical clamping and drilling jig. In this way we can place the wood strips vertically and use the drill press to drill perfect holes in the end of the strips.
How to make the vertical clamping and drilling jig for the drill press
Underneath the metal table of my drill press there is a bolt that holds the table attached to the clamp that goes around the column. By loosening that bolt  I can rotate the metallic table by 90 degrees and put it vertical. The problem is to put it perfectly vertical, since the table of my drill press has markings to put it perfectly horizontal, but not to put it vertical.
What I do is to put a drill bit in the drill press chuck, move the table against the drill bit, and adjust the position of the table until when I turn the drill press chuck by hand the helix of the drill bit rubs against the metal table both on the top  and on the bottom . And now, being very careful not to move the metal table, I have to tighten the bolt little by little , not forgetting to check and retouch the position of the table if necessary.
With the jigsaw I cut a piece of 18mm plywood , the base fro this clamping and drilling jig, slightly larger than the metal table of the drill press . I match one of the edges of the piece I want with one of the factory cutouts. This is to make sure that that edge of the piece I want is perfectly straight. Perfectly flush with that straight edge I want to put a small support strip  that will be used to hang the vertical plywood table from the top edge of the metal table of the drill press. And on the other face of the plywood table I’m going to put another strip at 90 degrees to the previous one . This second wood strip will serve as a lateral fence to keep vertically the wood strips that I want to drill.
To screw in the support strip, which will hold the plywood table vertical and help me adjust its position by moving it horizontally, I put the plywood table vertically on top of my workbench, with the factory straight edge against the table top. I put the support strip flush with that straight edge and I clamp it with spring clamps .
I drill three pilot holes  and drive three screws to attach the strip .
To screw the side fence strip, which will be vertical and will be used to put against it the wood strips to be drilled in the head while I hold them there vertically, I start by placing it more or less in the position I want it in and I put a screw in the upper part . With the help of the square I have to put it at 90 degrees to the first strip and clamp it with a spring clamp . After drilling a couple more pilot holes I attach it with a couple more screws .
Now I hang the plywood table from the edge of the metal table of the drill press, bring it close to the drill column and draw on the plywood the shape of the slots of the metal table . I separate the plywood table from the drill column and redraw the slots of the metal table . This way I have an area where the two drawings of each slot soincide . I make a mark more or less in the center and in those marks I drill holes to put two bolts .
I insert the bolts in the holes, with the head of the bolts in the face of the plywood where I put the fence strip, and with a narrow chisel I mark the hexagonal shape of the heads . With the same chisel I carve the hexagonal shape in the plywood  until I can fully embed the bolt heads . And by running a washer over the bolts I make sure they don’t protrude the surface .
I place the drill press laterally on the edge of my workbench and clamp it with a couple of clamps. And now I want to turn the drill head to the outside of my workbench.
To rotate the metal table I only have to loosen the clamp that holds it to the column. And turning the drill head isn’t much more complicated either, as it has a couple of Allen screws that hold it locked on top of the drill column. By loosening those screws I can rotate the head 90 degrees. I tighten the screws again and I already have the drill press ready to install the vertical clamping and drilling jig.
How to drill in the head of wood strips
I install the vertical clamping and drilling jig on the metal table by inserting the bolts through the slots of the metal table, but making sure the support strip rest fully on the top edge of the metal table. And I tighten it with some wing nuts, with the help of a couple of large washers and a couple of small washers . Now I have to put a drill bit in the drill chuck and move the table until the drill bit is right in the corner where the plywood meets the vertical fence strip. If, when turning by hand the drill press chuck, the drill bit rubs both against the plywood and the fence strip both at the top  and at the bottom , then the table and the fence strip are perfectly vertical and aligned with the drill bit.
I can now place the wood strip that I want to drill in my vertical drilling jig, well supported against the fence strip and more or less flush with the top of the plywood table.
I clamp it with a pair of spring clamps, and move the metal table sideways and the plywood table forward or backward until the tip of the drill bit falls just above the point I want to drill into the end of the strip. I tighten the metallic table clamp around the column, I tighten the wing nuts, make a final check to make sure the drill bit is right where I want to drill, …
and I can drill a perfectly precise and vertical hole in the en of the wood strip. This way I can drill perfect holes in the end of the wooden strips to make joints with dowels.
This drilling jig is perfect for making dowel joints, and we can use it in combination with the typical horizontal drill press table.