We study almost bi-paracontact structures on contact manifolds. We prove that if an almost bi-paracontact structure is defined on a contact manifold (M, η), then under some natural assumptions of integrability M carries two transverse bi-Legendrian structures. Conversely, if two transverse bi-Legendrian structures are defined on a contact manifold, then M admits an almost bi-paracontact structure. We define a canonical connection on an almost bi-paracontact manifold and we study its curvature properties, which resemble those of the Obata connection of a para-hypercomplex (or complex-product) manifold. Further, we prove that any contact metric manifold whose Reeb vector field belongs to the (κ, μ)-nullity distribution canonically carries an almost bi-paracontact structure and we apply the previous results to the theory of contact metric (κ, μ)-spaces.