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6. Gravenhurst

In Ontario’s Muskoka region is the lively town of Gravenhurst, ripe with cottagers staying for the dazzling landscapes and legion of lakes. The town is filled with opportunities to take in galleries and arts, antiques and vintage wares, and all kinds of interesting specialty items. The community is tight-laced and always hosting something fun, from Cinema Under the Stars (a weekly community film night) to special events downtown. The Muskoka Wharf is a sweeping, lakeside area dedicated to Gravenhurst’s diverse and unique history. The conglomeration of shopping, dining, and town heritage is put together magnificently in the waterfront retreat where there’s a featured Farmer’s Market, the annual Dockside Festival of the Arts, and Music on the Barge on Sunday’s in summer. Year-round there are special events, plays, and concerts at the Gravenhurst Opera House and also a bounty of parks with great swimming, public docks, and convenient facilities.

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5. Creemore

The town of Creemore looks like any small farm town in Ontario when just driving by. It might not seem like anything special—and it is quite small—but there’s more than meets the eye here. Old Victorian homes line streets, filled with mom and pop shops of all types, and where friendly is the name of the game. Set on the edge of the stunning Niagara Escarpment—a World Biosphere Reserve—and close to many fun destinations, Creemore wins almost anyone over. The handful of excellent art galleries combine perfectly with book shops, a small brewery, and super cool artisan shops (lots of creative types here). Scenic drives are the way to see rushing rivers, rolling hilltop farms, and perfect views of Georgian Bay. Bike, hike or walk the Ganaraska or Bruce Trail in the warmth or hit the cold for excellent snowshoeing and backcountry skiing.