I'm just a casual rider and don't mind stopping occasionally to enjoy the trail and the attractions near by. I live about a minute and a half from the Oak Leaf Trail and often use it.
I like to start by riding through Lake Park, a beautiful park designed by Fredric Law Olmsted, the same man that designed Central Park in NYC. It has bluffs overlooking the lake, tennis courts, lawn bowling courts, a par 3 golf course, kid's play areas and a lighthouse as well as great scenery.
Crossing the northern end of Lincoln Memorial Drive to the side that runs along the lake shore, you don't have to cross a street until you get to the art center. There are a few parking lot entrances and exits but not bad at all. Along the way, you ride past Bradford Beach and the many volleyball nets set up. The beach also has a "Tiki Bar" where you can purchase a beverage and sit down to a fantastic view of a great lake. Food is also served at the boathouse.
A little farther down the trail is a walk-up restaurant that serves great hamburgers and other sandwiches. The view can't be beat.
Rolling south, you ride right along the side of the lake and past McKinley Beach til you get to the breakwater and boat launch. It's worth a few minutes to go out on the breakwater. And it has another place to grab something to eat if you so wish. Just past the Milwaukee Yacht Club is Alterra Coffee. More food and coffee (obviously) as well as a terrific place to people watch.
If you take the cinder path on the south side of the small inlet where people are often fishing, you can go past lots of big and small boats in the marina. That will take you to a place where you can buy and fly kites if you like.
Again riding right next to the lake, you will go past the Milwaukee Art Center. If you get there at the right time, you can see the "wings" going up or down to classical music. Then there's Discovery World at Pier Wisconsin, Lake Shore State Park and of course, the Summerfest grounds. All of this right along the lake. Gorgeous.
And there are lots of events during the summer along the lake and at the Summerfest grounds. The trail is within easy biking distance of other city events like Bastille Days and the Brady Street Festival. Never a parking problem with a bike!
If you're racing, this isn't the way to go. However, if you're just enjoying a bike ride and don't mind occasionally getting off your bike and walking (because of the many people, especially on weekends), then this section can't be beat. Going from Lake Park to Lake Shore State Park and back is approximately 8-9 miles of pleasure. Early mornings are the best. Bring your camera. Smile and say hi to everyone and have fun!

well, it's finally happened. thanks to all the trail "boosters", the "freds" and other assorted morons have discovered the trail so that now, the trail is unrideable. my partner gave up on it some time back due to numerous close calls with bodily injury because of inattentive and thoughtless users of the trail. i continued using it as a way to add additional distance to my ride home from work-until yesterday. i've put up with all the dog owners who walk their dogs off leash, the walkers who walk on the wrong side, the people who stop on trail rather getting off the trail, and all the other oblivious users but yesterday just killed it for me. a group of half a dozen geezer freds chatting each other up and riding all over the trail caused me to wreck and sustain some minor injury. i was infuriated by their thoughtless inattention and refusal to admit their fault. if you're at all serious about cycling, i would not recommend the oak leaf trail. you'd be safer sticking to streets.

This past weekend I rode from Chicago to Milwaukee and part of the trip included the Oak Leaf Trail. I started at the southern end of Grant Park and rode all the way downtown to where I was staying. I have to say, it was probably the best part of my trip. At the south end of the park, there is a beach and harbor with great views. The park itself is mostly wooded with plenty of wildlife. It is windy with just enough hills to keep things interesting. As I went further north, the trail ends up meandering along the lake with spectacular views of the water and eventually the Milwaukee skyline. I was very happy to have my camera along!

On the negative side, some of the path through the trees is not well kept. There were times where I couldn't tell if I was still on the paved path or if I had meandered onto a side dirt trail. It wasn't unusable and the trail was interesting enough that I almost immediately forgot about the trail conditions, but there was certainly room for improvement there.