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Winter Park really consists of three separate areas; the ski resort area itself, the town of Winter Park and the town of Fraser. The area operates an excellent shuttle system that makes stops in town and picks up passengers from the local hotels and inns. It is not really necessary to have a private vehicle unless you wish to go further afield than the shuttle will take you. It is also unwise to think that it's an easy stroll from the ski area to the town; the area is large and they run a shuttle for good reason. Restaurants are mostly located along the main road in downtown Winter Park, along with shops and stores. The main grocery (Safeway) is located nearby in Fraser, close to the Visitor's Center. The towns are small, clean and very walkable. There is also a twice-daily AmTrac train stop in Fraser and the Ski Express train which which historically brings up skiiers from the Denver area on weekends. So it is possible with the right planning, not to have to worry about "your ride" at all while visiting during ski season.
Skiers and other visitors with disabilities can also take advantage of a free dedicated bus service called Paratransit, which will pick people up at their door when called. The service runs from 8am to 11pm, the response time is usually 5-10 minutes, and the drivers will assist with bags etc as required. Phone 970 726 4163.
The ski resort presents its own challenges as far as navigation is concerned. It is big and sprawling, with the main bottom lifts spread out to such a degree that there will be walking involved, especially for beginners, from one area to another at the base. Trail maps do not always reveal the high number of green (easy) routes available from the top of some of the lifts. If in doubt, ask a lift operator or send up a skilled member of your party to check out the options. Winter Park has a lot of advanced terrain located adjacent to easy slopes, so it is good to pay attention to the trail markers, which are liberally and accurately distributed. It is also good to remember that the area is actually subdivided to cater to the differing levels of expertise, with the novice area farthest afield (to the right as you look up at the mountains) from the village base.