Transit to Trails Act of 2019 This bill directs the Department of Transportation (DOT) to establish the Transit to Trails Grant Program to award grants to certain governmental and private entities for projects that increase transportation access to public lands, waters, parkland, or monuments for critically underserved communities. Among other things, the bill requires DOT to develop transportation planning procedures for projects conducted under the program that are consistent with metropolitan and statewide planning processes, grant recipients to contribute matching funds equal to not less than 100% of the grant amount, grant awards to be at least $25,000 and not more than $500,000, and publicized schedules and routes for transportation systems that are developed after the receipt of a grant under the program.