The best running trails around Headingley

The Monkey Trails circle Assiniboine Park and are informal dirt trails open to mountain biking, winter fat biking, hiking, trail running, and snowshoeing. They offer nice views of the Assiniboine River, circle the zoo, and leave the park heading east following the river.

The Assiniboine Park Conservancy Inc. is a non-profit charitable organization that was established in 2008. It was created to oversee the development of the 162 hectare Assiniboine Park. This building was built almost 100 years ago in 1930 in Tudor Revival architecture with Swiss chalet elements and a 28-meter central square tower rising above the park. Today, it is used as a multilevel public cultural space with free art galleries, a museum dedicated to Winnie-the-Poo and the grounds have a rectangular lily pond, and sculptures for the public to enjoy.

The Riley Family Duck Pond was designed with an organic shape in mind, with small islands, a pedestrian bridge, perennial plantings, and is a home to waterfowl. In the warmer months, the central water fountain, a floating bio-island ecosystem, and entries for small canoeing make it a charming home for ducks, geese, and turtles. In colder months and winter, the pond is transformed into a large, outdoor skating rink with festive overhead light displays. Pucks and hockey sticks are not allowed on the ice to ensure a safe, family-friendly free skate time.

This large open green space offers an clear view towards Winnipeg Richardson International Airport thanks to the lack of trees and surrounding obstructions. Aircraft regularly pass overhead on approach and departure, making it a surprisingly good spot for a bit of plane watching while following the Yellow Ribbon Greenway. The mostly level terrain and wide-open sightlines also provide long views across the surrounding area, giving the park a much more open feel than many of Winnipeg's urban green spaces.

Stretching for approximately 5 kilometres, the Yellow Ribbon Greenway links Silver Avenue near Saskatchewan Avenue with Bruce Avenue in west Winnipeg. The paved multi-use trail passes through parks, sports fields, residential green spaces, and Air Force Heritage Park, creating a continuous corridor for walking, running, and cycling. Developed in partnership with 17 Wing Winnipeg, the greenway serves as a tribute to Canadian Armed Forces members who have served overseas, with interpretive features found along the route.

A collection of Royal Canadian Air Force aircraft lines the grounds of Air Force Heritage Park, offering a close look at several decades of Canadian military aviation. Highlights include the CF-104 Starfighter, CF-101 Voodoo, CF-100 Canuck, CT-133 Silver Star, and a Bell Kiowa helicopter. Many of the aircraft are displayed outdoors on static exhibit, making this a worthwhile stop for aviation enthusiasts and anyone interested in Canada's air force history.

There are a few nice paved trails to explore in the park, and the north side has some fairy houses and a cenotaph (empty burial memorial) to veterans of the first world war. You cross the creek via a pretty pedestrian bridge as it winds into the Assiniboine River.

Two long benches have been built by a clearing on the riverbank and offer a tranquil view of the Assiniboine. You can walk over via the singletrack Monkey Trail or the paved Wellington Crescent Trail. The path down to the lookout is accessible, well-maintained crushed gravel.