Day: Discover local food, art and history

Start your explorations on Orillia’s Mississaga Street, a hub of shops and galleries that slopes down gently to the shores of Lake Couchiching. Browse boutiques that carry everything from watches (at the aptly named Perfect Timing) to Scottish specialties (including, yes, bagpipes and kilts), or discover works by local artists (and meet resident pup Mojo) at Coach House Gallery.

Pause for a coffee and home-baked treat at Mariposa Market, or sit under the skylights in the market’s Back Porch area for a lunch of freshly made soups, salads or sandwiches. After refuelling, pop around the corner to the Orillia Museum of Art and History, whose rotating exhibits are displayed in a former post office turned police station. (If you visit on a weekday, you may even be able to visit the remaining jail cells in the basement.)

Night: Catch a performance at the Orillia Opera House

Reserve one of the 700 seats in this heritage building’s auditorium for live theatre, a show by a local dance troupe or a concert by a touring band.

Option 2: Take a walk, then treat yourself to dinner and a show

Day: Stroll in Grant’s Woods

Head north of Orillia to Grant’s Woods, where four kilometres of looped, well-marked trails lead visitors through nearly 52 acres of old-growth forest that were once home to the Grant family. Today, they’re home to huge trees, ferns and wildflowers, several bird species, an abandoned truck (great for photos) and the occasional site-specific art exhibit.

If you drive back through Orillia to the nighttime stop, be sure to watch for signs for the Mnjikaning Fish Weirs National Historic Site near the bridge over The Narrows between Lake Couchiching and Lake Simcoe. Here, the Huron-Wendat First Nations drove sharpened wooden stakes into the lake bed to build weirs, or mazes that trapped fish swimming between the lakes.

Night: Head to Casino Rama for dinner and a show

The design and decor of Casino Rama reflect the area’s fishing heritage—namely in The Weirs Restaurant, but also in the splurge-worthy steakhouse St. Germain’s. Whether you go for casual pub favourites or an indulgent dinner of AAA Alberta beef, take a moment after dessert to look for weir motifs hidden in the eateries.

See if you can spot even more as you make your way through the Hall of Grandfathers to the entertainment centre for a performance by the likes of Bryan Adams, the Beach Boys or Russell Peters.

Option 3: Trace the region’s military heritage—and pick up a few souvenirs

Day: Take a tour, enjoy a tasting

Make your way to the hills outside Barrie for a tour of Heritage Estate Winery and Cidery. During the War of 1812, the land was a farm along the busy main route from Fort York to Penetanguishene on Georgian Bay. Owner Peter McArthur's family bought it in 1855 (hence the "heritage" part of the name) and it's now over 20 acres of peaceful vineyard. Learn about how McArthur and his team make wine, craft cider, sparkling apple wine (“totally fun”) and a blueberry-apple sangria (“barrels of fun”), and pick up a bottle or two to take home.

Mosey down the road to Chelsea Chocolates, where owner Laurie Thompson offers up confections with Heritage Estate cider in the filling along with a host of other Callebaut chocolate–coated treats.

Night: Sit down to a waterfront dinner at a former fort

Continue on to Penetanguishene and Discovery Harbour, where you can see how sailors lived at this naval outpost on Lake Huron in the 19th century. The historic site also hosts special events from a winter skate trail and summer ghost tours to the popular Pumpkinferno around Halloween. Grab a table at Captain Roberts’ Table Restaurant on the boardwalk and watch the replica tall ships bob in the bay as the sun sets.

Looking for more great itineraries for travel in Canada?

Find out the five culinary trails in Stratford that you shouldn’t miss and discover the unexpected delights of B.C.’s Ale Trail. Plus, get even more great ideas from our Road Trips stories.

Image Credits: Couchiching Conservancy, Casino Rama, City of Orillia, Heritage Estate Winery and Cidery