Our area offers some great outdoor activities. My favourites are cycling, skiing and hiking. I would like to tell you abit about them.
CYCLING. The local area has a great choice of both quiet on-road and off road routes. The further north you go, the safer the roads become. If you want hills, try county road 17 and 21 in Mulmur. A  great workout and fantastic scenery. In 2006, I cycled across Canada (www.tourducanadacom). When going thru the area on County road 17, some one said that it was the most scenic road since the rockies. I have recorded a speed of 87.4 kph on my tandem bike on one of these hills. If you want to avoid hills, pick routes thru Amaranth or quieter still in Melancthon (wind turbine country). Orangeville has a cycling club that does road rides on Weds evenings as well as off road events (www.hbcc.com). I trained with them prior to the big ride in 2006.
CROSS COUNTRY SKIING. There is a great facility  on the north end of Orangeville (in behind the car dealerships. They have groomed trails for both classic and skaters. Check out www.mononordic.com. There is also good skiing at the Mansfield outdoor centre (Airport road about 4 kms north of Mansfield (www.mansfieldoutdoorcentre.ca). Both places have rentals. I also ski on the snowmobile trails around Primrose or make my own on the provincial property northwest of Primrose. 
DOWNHILL SKIING. Your choice of local hills (Hockley or Mansfield) or an hours drive gets you to Collingwood or the Beaver Valley). Lots to pick from.
HIKING. The world famous Bruce trail goes thru Dufferin county for about 110 kms. It goes from Niagara Falls to Tobermory and offers great hiking and views.More info at www.brucetrail.org. Part of the trail goes thru Mono Cliffs park (www.ontarioparks.com/english/mono.html). Great choices for a quick hike or an all day adventure.
We hope that you get to enjoy the Dufferin county outdoors as much as we do.