If you want to stay away from streets altogether, there are a number of trails you can consider. There is the Martin Goodman Trail, Moore Park Ravine, Tommy Thompson Park, Don River to the East, the Humber trail to the West, and the Waterfront system along the shores of Lake Ontario.
Obamacare plans are private plans; Medicaid is government-run coverage. The most important difference between Medicaid and Obamacare is that Obamacare health plans are offered by private health insurance companies while Medicaid is a government program.
Eligibility requirements for Medicaid vary by state, and you should check with your state Medicaid office (or website) for more information on that and for enrollment information. The difference between Medicare and Medicaid in a nutshell, then, is this: Medicare is an insurance program primarily for older Americans. It's the same for all Americans, requires them to share some costs, and is administered federally.