Hi Jake,
Amanda has already provided a pretty good listing, so I'll merely provide additional options.
Winnipeg is actually quite good for cycling spots within the city: if you're cruising go to Assiniboine park and cruise around the paths and over the bridge to Sargent Sundae. If you're up for more dirt, go south to the Assiniboine Forest.
Across the river, near the Forks is Whittier Park and there are some challenging trails through there.
http://biketothefuture.org/commuter-cyclists-resources/tips/winnipeg-cycling-map

When hungry, Winnipeg is noted for its plethora of burger joints serving their own take on the "Fat Boy"; a big burger often slathered with chilli. Daly Burger, Super Boy's, Blondie's, Park Tower, too many to name - search on urbanspoon.com for more. While you're at it, hit a 7-11 for a slurpee to help us retain our Slurpee Capital claim.

Once you're all done this activity, chill out on a patio on the Corydon Strip; because as soon as it's above freezing Winnipeggers want to be on a patio!

Catch the sunset over the city's downtown from the Provencher Bridge (at the Forks).

Enjoy a pint at Toad in the Hole pub in Osborne Village, or the King's Head in Exchange are good spots.
Live music at Times Changed cafe on Main.

The Manitoba Museum downtown is quite good, so is the Winnipeg Art Gallery. Loads of other artsy shops in the Exchange.

Dirt track car racing is 30min south of the city. Horse racing is on western edge.

Enjoy the 'Peg!

Posted Jul 31, 2012

First of all Welcome to Winnipeg!

1) Definitely go to The Forks, you can bike throughout most of it, along the river but plenty of places to walk around. Right beside it is the brand new Human Rights Museum, not yet opened but it looks beautiful. Check out the Forks Market and enjoy some delicious food!

2) Walk around Winnipeg Downtown's Exchange District, (google this) but includes the streets Bannatyne, Albert, and McDermott ave. TONS of movies have been filmed in this area because it looks like Old Chicago. Definitely check out Old Market Square, also in the Exchange District as well.

3) When are you coming? Folklorama starts Aug 5th, its the biggest and longest running Folk fest in the world! Check it out, http://www.folklorama.ca/

4) If you like Shopping Polo Park Mall is pretty great, and next to it, is the Bomber Stadium - see a football game if you can, lots of fun. If you two prefer boutiques that are really interesting, head down to Osborne Village (google it) - voted Canada's Best Neighbourhood 2012!

5) Something romantic: Eat at Fude in Osborne Village - local eats and really crazy concocsions but I've always had a fabulous time there! Get the chili chocolate chicken skewers! Delish!!
If you want something more safe: Earls on Main Street has the best patio in the city, another cool patio is the rooftop patio at Tavern United Downtown.

Hope these helps! Have a great time in Winnipeg!!
Amanda

Posted Jul 31, 2012

Assiniboine Park: free entertainment every day in the summer, AMAZING Children's Garden, and TWO fantastic restaurants: one fancy, one casual. AND, it's just a quick walk over the pedestrian bridge to Sergeant Sunday. AND there is the Zoo, which is getting a huge facelift right now. Oh - AND a REAL steam train! I love that park!
The Leo Mol Sculpture Gardens are amazing & free!
http://www.assiniboinepark.ca/attractions/gardens.php

Shakespeare in the Ruins - Amazing shows in an incredible setting at the Trappist Monastery Heritage Provincial Park in St. Norbert, just outside the city limits. This is worth any additional effort to get to. World renown productions.

First Friday of every month in the Exchange District artists, studios & unique local shops open their doors for an amazing tour. There is a web site. This would make a tour of the Exchange a lot more significant and interesting than just walking around.

If you're going to go to the Forks, ride across Provencher Bridge into the French Quarter in St Boniface and check out the Cathedral. Very cool & unique. http://www.cathedralestboniface.ca/main.php?p=62

I concur with the previous comments about The Kings Head in the Exchange & the Toad in Osborne Village being a great place for a pint.

Personally I wouldn't waste a second on malls or commercial development. No different than anywhere else in the world.

Posted Aug 01, 2012