Academy Road and Assiniboine Park

Spend a day or a weekend exploring one of the main streets of Winnipeg’s River Heights neighbourhood – Academy Road. Dotted with local shops and restaurants, and bookended with Winnipeg’s largest park and the grand houses of Wellington Crescent, there is plenty to explore along this 3 km stretch.

Winnipeg Aerial View
Enviro Foto

Though Academy is a short stretch of road south of the Assiniboine River, it offers many opportunities for discovery and exploration.

On Academy Road’s main stretch, between Oak Street and Centennial Street, are an abundance of local shops and restaurants. Some businesses are housed in old buildings that were once schools, telephone exchanges and homes, reminders of Academy Road’s long history, which can be explored through a self-guided walking tour. On it’s far East end, sits 529 Wellington, a fine dining restaurant housed in a 1913 mansion. Just past the West end of Academy Road is Assiniboine Park, offering visitors large expanses of greenspace, manicured gardens and outdoor art to enjoy.

Winnipeg is located on Treaty 1 territory.

Summer Trip

Top Stops

  • Eat + Shop along Academy Road: Visit local shops and restaurants along this 3 km stretch
  • Assiniboine Park Zoo: An underwater tunnel and conservation education await at the zoo
  • English Gardens: A beautifully landscaped garden and home to the Leo Mol sculpture garden

Where To Stay

If There’s Time

  • Historic Walking Tour: See Academy road’s historic buildings on a self-guided walking tour
  • Bee2gether Bikes: Rent tandem and buggy bicycles for the whole family to explore Assiniboine Park
  • Tuxedo Golf Course: 18-hole golf course south of Assiniboine Park

PART 1 – Stroll through history

Step back in time to discover the history of the Academy road area. Along the 25-point self-guided walking tour from the Academy Road Biz, you’ll see a range of architectural styles and buildings that you may not have thought to stop and look at without a virtual guide. Admire the turn-of-the-century businesses, the iconic Uptown Theatre, the grandiose houses of Wellington Crescent and the outdoor artistry of current neighbourhood residents. On foot, the 9 km loop takes approximately two hours to walk, but we recommend taking the time to make a few extra stops at local businesses and restaurants along the way.

Person walking along rocky horizon in Flin Flon
Person posing on rocky hill top overlooking the river near Flin Flon.
A person watches the sunset from a viewing platform in Flin Flon.
Aerial view of a river cutting through a forest

PART 2 – Eat + Shop on Academy road

As you stroll along the loop that shows you pieces of Academy Road’s past, stop into old and new buildings that now house a wide variety of shops and restaurants.

Shop locally owned businesses that offer everything from home and lifestyle wares (visit Salt Boutique and Grace & Company), to clothing and accessories (visit Margot + Maude, Mad About Style, Chestnut Lane Boutique or North Flag) and lots in between.

For dining options check out Pizzeria Gusto (elevated Italian cuisine), Leopold's tavern (casual pub atmosphere), 529 Wellington (fine dining steakhouse), or Saucers Café (elevated casual eats using local ingredients). Or if you’re just looking for a quick sweet or savoury treat, try Jenna Rae Cakes (boutique bakery), G.I. Andrews (premier specialty food and wine shop), Cornelia Bean (loose leaf tea and freshly roasted coffees) or Bernard Callebaut Chocolates (fine specialty chocolates).

View of Main Street in Flin Flon on a sunny day.

529 Wellington

An elegant steakhouse with exceptional service, housed in the J. Ashdown House, built in 1913. Serving cooked-to-perfection steak, seafood and sides to share for dinner and lunch.

Jenna Rae Cakes

This boutique bakery specializes in macarons, cupcakes and cookie sandwiches in flavours from brownie batter to sour fuzzy peach.

North Flag

A lifestyle brand selling designed-in-Winnipeg clothing, hats and accessories. Home to Winnipeg is Good and Middle Province merchandise.

A family of four admires a sculpture of two loggers at the Leo Mol Garden.

PART 3 – Afternoon at the park

Assiniboine Park

Just past the West end of Academy road is Winnipeg’s largest park – Assiniboine Park. The park and the adjoining Assiniboine Forest cover a total of 1,100 acres of land. The landscaped portion of the park takes up 400 acres between the Assiniboine River and Corydon Avenue. The park is a perfect destination for an afternoon of outdoor activity for the whole family. There is plenty of greenspace for a picnic, kite flying or throwing a frisbee, beautiful English gardens that also house the Leo Mol sculpture garden, opportunities for bike rentals for the whole family and a large nature playground for kids. The Park Café is an ideal spot to stop for a quick snack or a full delicious meal while spending an afternoon in the park.


Explore the Journey to Churchill exhibit

The zoo offers opportunities to get up close to animals from around the world and from Manitoba. For an awe-inspiring view of the animals, step into the Sea Ice Passage – an underwater tunnel where the polar bears and seals swim above and beside you.


Summer evenings in Assiniboine Park are often filled with music, theatre, dance and movie screenings during the Summer Entertainment Series. This collection of free events typically runs from June through August at the outdoor Lyric Theatre. Performances are often made by Winnipeg favourites like the Royal Winnipeg Ballet, the Winnipeg Symphony Orchestra and various local bands and jazz groups.

Assiniboine Park Lyric Theatre/Stage