York, Durham and Headwaters

York, Durham and Headwaters are three regions that are close enough to downtown Toronto to access all that the big city has to offer, but also just far enough away to deliver refreshingly laid-back experiences, perfect for a day trip or weekend getaway.

To learn more about all there is to see and do in York, Durham and Headwaters, scroll down or visit the region's tourism website

Where is York, Durham and Headwaters?

Also known as the Golden Horseshoe Region, York, Durham and Headwaters halo the outer fringes of the Greater Toronto Area like a crescent and extend up to the southern shore of Lake Simcoe. 

Places to Visit in York, Durham and Headwaters

Key cities in this region include Orangeville and Caledon in Headwaters, Markham, Vaughan and Richmond Hill in York Region and Oshawa, Uxbridge and Port Perry in Durham Region. 

Show your love of Emmy winning show, Schitt’s Creek with a selfie in front of the Rosebud Motel in Orangeville. Nearby, Hockley Valley is a luxury resort complete with fine dining, a golf course, spa facilities, onsite ski hill and a sister winery and tasting room overlooking the vineyard. Moira Rose and her collection of wigs would approve. 

Bring your budding astrologists to check out Canada’s largest reflector telescope at the David Dunlap Observatory in Richmond Hill. 

Creative and refreshing craft breweries can be found in discerning communities across Ontario and Durham is one of them. From Second Wedge in Uxbridge, Brock St. Brewing in Whitby to All or Nothing Brewing in Oshawa, taste the quality in small batch, pride of place brews.

Things to Do in York, Durham and Headwaters

Much of Ontario’s Greenbelt, a ribbon of protected forest, wetlands and watersheds that surrounds the Greater Toronto Area, lies within York, Durham and Headwaters, blessing this region with amazing, accessible natural spaces. From valley river forks to lofty lookouts, hike, bike or snowshoe the trails in one of numerous parks and conservation areas. West of Caledon, Cheltenham Badlands is an amazing geological site of undulating rust and red coloured rocks, the result of exposed and eroded shale. Accessible boardwalks and trails lead you to view this designated natural heritage site.  

Headwaters communities around Orangeville, Caledon, Dufferin County, Erin, Mono and Shelburne make up the hub of Ontario’s horse country. Set out on a trail ride or take horseback riding lessons at a stable or farm. 

The rolling hills, lush forest and pastoral countryside are prime for golfing. Tee up for a round on one of the many PGA quality golf courses and resorts, designed by legendary golf architects.  

From local artists’ studios to one of the largest collections of artworks by the Group of Seven at the McMichael Canadian Art Collection, there’s never-ending opportunities for artistic inspiration. Shop for treasures at antique stalls, farmers' markets or in historic main streets. 

For larger-than-life fun, choose from a selection of theme parks and outdoor adventures, including Canada's Wonderland

The region extends up to Lake Simcoe, one of Ontario’s largest inland lakes, billed as the Ice Fishing Capital of Canada. Operators offer guided excursions, perfect for an excursion or family adventure. 

Last updated: October 20, 2021

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