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.
The following will hopefully help you understand what these terms are and the differences between them. Medicare is a Federal program which provides basic health insurance to everyone over age 65, and people who are under 65 but are eligible for Social Security Disability benefits. Medicaid is a joint Federal-State program which provides (among other things) long-term care for seniors.