I cheated and used a CNC, but I know you can buy a jig on Amazon or from Rockler and use a drill press. Here’s an example of a jig: ChefwareKits 484 Cribbage Board Template 3 Lane Starter Kit with Pegs and Drill Bits https://www.amazon.com/dp/B00BQL9LUC/ref=cm_sw_r_cp_api_i_FMQMPZ1XF1QCWRDAKQ4P