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The Detroit side should probably hook up with its great RiverWalk system at least. I don’t see the same opportunities on the Windsor side.
The obvious attraction on the Canadian side would be Ojibway. (The border plaza being just about the top-right of this map). I'm not sure if there are any plans at the moment to make that a nice connection. There's also a trail they built alongside the Herb Gray Parkway to the new bridge.

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The obvious attraction on the Canadian side would be Ojibway. (The border plaza being just about the top-right of this map). I'm not sure if there are any plans at the moment to make that a nice connection. There's also a trail they built alongside the Herb Gray Parkway to the new bridge.

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I find it funny they call the 401 only "Herb Gray Pkwy." yet its not even signed on the 401.
 
I find it funny they call the 401 only "Herb Gray Pkwy." yet its not even signed on the 401.
It existed long before the 401 was extended and signs went up after the bridge was proposed as well to be built. This was after the expansion took place.
 
The MUP system on the Canadian side is a little funky. There is going to be a full connection with the Herb Gray Parkway trail but it's a bit convoluted. The trail system will run along the PAR (Perimeter Access Road) from the bridge to Sandwich Street (northern portion of the PAR) and to Broadway Street (southern portion of the PAR). The MUP will cross Ojibway Parkway at Broadway Street and continue on the eastern portion of Broadway Street, where the MUP has yet to be constructed. That portion of the MUP will run east to Matchett and connect with the existing MUP there. That portion runs north toward Malden Park, which connects it with those paved trails. From this point, there is a MUP that runs along the southern boundary of Malden Park and connects to the MUP at Malden Road, which runs south to where it finally connects with the Herb Gray Parkway trailhead. The MUP will also extend along Sandwich Street into the Sandwich neighbourhood in west Windsor until about Chappell Street, after which, the street will have bike lanes running until about Rosedale Avenue near the Ambassador Bridge. Details on the MUP and Sandwich Street construction projects are linked.

I would personally prefer if they just ran another MUP on the south side of the Herb Gray Parkway from Matchett to Malden so it would be a proper direct connection between the Broadway MUP and the Herb Gray Parkway trail, but I don't think there are any plans for that yet and is likely in the hands of the province to make happen. Additionally, there is unfortunately no direct Gordie Howe Bridge or Herb Gray Parkway MUP connection to the Windsor Riverfront Trail. The closest you can really get from the Herb Gray Parkway trail is Malden Park. You can kind of get further by biking along Carmichael Road through Mic Mac Park to the ETR trail along College Avenue, which ends just near the Ambassador Bridge plaza, but Mic Mac Park is not designed for biking. My wife and I used to walk and bike in this area when we lived in Windsor to get to the Herb Gray trail. Unfortunately we sometimes got harassed by Plains Midstream/BP security if we were there at an odd time (like later at night) since they have a facility right next to Mic Mac Park along Carmichael Road and biking along that road is unusual.
 

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