Cooler by the lake
(To view a larger map of the Oak Leaf Trail, click here)
Oak Leaf Trail – Southeast Segment
Enter the trail at the southernmost approaches to the Hoan Bridge at Cupertino Park. Ride past the South Shore Yacht Club into South Shore Park. Stop and enjoy the beach, the snack bar, or the playground. Continue along the lakeshore enjoying the view of sailboats, powerboats, and kayaks. In Bay View Park, you will climb up the bluff and enjoy a pleasant ride as you meander along the trail.
The entrance to Seven Bridges Trail. Photo by Carrie Trousil.
Continue along the bike path as it parallels Superior Street in St. Francis. Be careful on the sharp left corner that will take you back to the lake and around the condos. Take a moment to drink in this unobstructed view of Lake Michigan – quite the difference from when the South Shore power station was in existence.
Entering Sheridan Park, check out the pond, which is the operation site for the Wisconsin Scale Boating Association. On Sundays from 1-3 p.m. you might be able to catch the scale boaters in action. You might also consider walking down one of the paths down to the lakeshore. But remember, you have to come back up!
After passing through Sheridan Park you will enter Warnimont Park. You will ride by the Cudahy Sportsman’s Club, so don’t be shocked by the gunfire. No, they’re not shooting at you, just those darned clay pigeons. Ride carefully through this curvy wild area.
As you enter Grant Park you have two choices (in my opinion): you can follow the off-road path through the park or the parkway. I ride the parkway because I don’t feel safe on the path at the speeds I ride. But the path is a very wonderful way to get to see the park. Take it easy and enjoy.
Grant Park is also home to the Seven Bridges Trail, described as a “easy hike through woods and ravines, and offers beach access.” It is also known as one of Milwaukee’s haunted hot spots. Enter if you dare! It is a hauntingly beautiful area. The Grant Park Golf Course Clubhouse is the 8 mile mark on our ride down from Bay View.
If you want to go further, go past the clubhouse and enjoy the hill down to the Oak Creek Parkway. It’s a beautiful ride through the ravines and alongside the flowing river, and at the end you can stop for some refreshment at Dairy Queen! Continue along the parkway and then the off road path for about 2.5 miles and you will be at Drexel Ave. From here you can connect to the Southwest portion of the Oak Leaf or you can connect to the North Shore spur of the Oak Leaf trail ( we’ll talk more about that section in a future story).
Hope you enjoy the ride! See you next week as we head north from the Summerfest grounds.
