Best Places to Run in Chicago: Montrose Harbor

Montrose Park is located near the Buena Park neighborhood on the city's North Side

bethany 1
Bethany Stripp

The Lakefront Trail offers plenty of incredible views of the city, but as far as I’m concerned, none compare to the view at Montrose Harbor.

When I become bored of the usual out-and-back on the Lakefront Trail or just need a break from the hectic state of the Trail during the summer, I like to veer off the trail just south Montrose Avenue. Instead of turning left towards Cricket Hill, I continue on straight to Montrose Harbor.

During the summer, the harbor teems with activity. Several people are out fishing, and even more people sit out on their boats enjoying the weather. You’ll occasionally encounter a few other runners along this concrete path, but traffic is usually much lighter than what you find on the Lakefront Trail itself. I continue running east and follow the curve of the harbor south. Once the path turns east again, I take the first left and cross Montrose.

When you cross Montrose at this point, you have to briefly run across the grass before picking up a paved trail. This area, more than any other I’ve found, offers the best opportunity to completely forget you’re in the third biggest city in the United States. This area, just south of The Magic Hedge, is quiet and offers an incredible oasis from the busyness of city life. You can generally hear plenty of birds singing, and I’ve even seen a rabbit or two hopping around, which is not something I often see on busier portions of the Lakefront Trail.

While you enjoy the oasis, however, you're never far from the city. If you keep following the paved trail, you’ll turn right, and boom: skyline.

I rarely stop for anything other than traffic lights and emergencies on a run, but more than once I’ve stopped in my tracks at the view of the city from this point. You’re far enough north to see the entire skyline from Lakeview all the way to downtown, and it really is something to behold, especially on a clear summer afternoon as sailboats bob around on Lake Michigan.

From here, I run west along the path as long as it will let me before doing a 180-degree turn and retracing my steps back to the official Lakefront Trail. All told, this detour adds somewhere around a mile to your run, depending on where you take your turns. If you happen to be in the area, I highly recommend this detour!

Bethany Stripp is a local runner and the editor-in-chief of Chicago Athlete magazine.

Contact Us