Headwaters’ proudly preserved-towns, villages and hamlets are alive and weller than ever. And while there are eight distinctive destinations below, there are almost 40 on our map and double that in total. You never know which one will have a waterfall, a café, or a history that will strike a chord with you, so use these as points on a map of real. And when the road in-between them reveals somewhere new, follow it. Because you just never know.


Village of Erin

Village-of-ErinFounded: 1820
Population: 2,674
Km from Toronto: 81

Charm epitomized, Erin is a postcard: rolling hills, meandering rivers, cozy hamlets and villages. Its bustling downtown is a medley of adorable shops and lovingly preserved buildings. Must- see: the epic Erin Fall Fair, Thanksgiving weekend; the Erin Town Crier, who announces big news; lovely, strollable trails like the Elora Cataract Trailway.

No crocodiles allowed (bylaw 13-34).



Founded: 1822
Population: 479
Km from Toronto: 60

Cozy, picturesque and historic, with many designated heritage properties. The 1887-built General Store overlooks the Credit River and sits on the Bruce Trail; after your hike, drive three minutes to refresh at the stunning Spirit Tree Estate Cidery; four more minutes and you’re in the hot-tub at the 180-year-old Top of the Hill B&B.

While many municipalities forbid annoying yelling and shouting, Cheltenham also forbids hooting.



Alton-Mill-IllustrationFounded: 1855
Population: 895
Km from Toronto: 77

What seems like a quiet, historic village on rolling water is full of surprises. Like the Alton Mill, Ontario’s most beautiful arts centre filled with open-to-the-public artist’s studios; Osprey Valley Golf, Canada’s best three course facility; and unassuming Ray’s 3rd Generation Bakery. Goodies, yes, but also raved-about gourmet meals.

If you need to replace your marriage license here, it’s $50.00.


Grand Valley

Grand-ValleyFounded: 1855
Population: 2,726
Km from Toronto: 101

Grab a lunch (don’t forget the fries & gravy) from classic diner Kelly’s Korner, then picnic along the gentle Grand River which snakes through a town that hasn’t changed in a century. The ecologically important, bird-paradise wetlands of Luther Marsh are also a must-see.

The schnitzel at The Grand River Chop House is bigger than your head.



ShelburneFounded: 1879
Population: 6,500
Km from Toronto: 103

This authentic farming community keeps two important historical traditions very much alive: the Heritage Music Festival (formerly The Shelburne Fiddle Fest) is one of the last iconic rural music events, including a magical barn dance; the Shelburne Fall Fair gives you pie contests, tractor races, and a trip back in time. Both are ridiculously affordable.

When entering or leaving the Fair by car, avoid the Demolition Derby.


Mono Centre

Mono-Centre-IllustrationFounded: 1823
Population: around 500
Km from Toronto: 94

Mono’s motto is “the heart of the Headwaters,” named for the creeks and streams that are the headwaters of the Humber, Credit and Grand Rivers. Epic, escarpment-type nature surrounds, like Mono Cliffs Provincial Park and its great caving. Another favourite cave is Peter Cellar’s Pub, the unique basement bar in the celebrated Mono Cliffs Inn.

The mayor of Mono makes over 8,000 pies a year, which, while unverified, is considerably more than most mayors.



OrangevilleFounded: 1863
Population: 27,975
Km from Toronto: 79

Of course you’ll stroll downtown with its superb restaurants and funky shops, but there’s more to this artistic, tree- lined town. Side streets reveal restored Victorian homes, its professional theatre debuts major Canadian plays, and the free Orangeville Blues and Jazz Festival invites you into dozens of town hotspots that host some 80 acts.

The ghosts reported in the Orangeville Library are messy but harmless.


Caledon East

Caledon-EastFounded: 1820
Population: 3,070
Km from Toronto: 64

Caledon’s greenery and views “rival Tuscany,” says Gilles Roche, transplanted European chef and co-owner of Gourmandissimo, a beloved food emporium. The village’s natural beauty yearns to be explored: the 35 km Caledon Trailway (part of the Trans Canada Trail) follows an abandoned rail line—hiking/ walking, cycling on & off-road, and equestrian and winter snowshoeing use.

You must get Council’s permission to have a drag strip.