Paddle Chicago: Stand Up Paddle Boarding at Osterman Beach

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The Lakefront Trail in Chicago is 18 miles long and has beautiful views of Lake Michigan, area beaches, the Chicago skyline, and even a little wilderness the entire way.  In the summer, you'll find tourists and locals using the trail for many reasons.  I personally use this trail weekly for beautiful jogs, biking to work, and of course, transporting my inflatable stand up paddle board (iSUP)

The north end of the trail ends at Ardmore Ave, which also happens to be Kathy Osterman Beach, aka Hollywood Beach.  I've biked to the north end of the lakefront trail many times and always noticed how beautiful and peaceful Osterman Beach seems to be, but it's about 7 miles from my apartment and the logistics of getting my iSUP there is more challenging.  This weekend, I finally made it to Osterman Beach with my iSUP and it didn't disappoint!  Osterman Beach is a designated launch site on the Lake Michigan Water Trail and the beach is just gorgeous.  The scene is very chill on the weekends, which is a bit different than other Chicago beaches.  The water seems much calmer, too - it's a great place to try SUP yoga!  

Kathy Osterman Beach Break Wall

Kathy Osterman Beach Break Wall

Paddle Board View, Osterman Beach

Paddle Board View, Osterman Beach

My plan for this trip was to paddle from Osterman Beach to Montrose Harbor, which is about a 3.5 mile paddle.  Since I wasn’t returning to my launch point, I ordered a ride share to transport my board and I to the beach.  I'd normally use my bike trailer and ride to the beach, but I wanted some flexibility.  I believe there is street parking at this beach, but the neighborhood can be a little sketchy.  However, I have locked my bike up here with no problems. 

I pumped up my iSUP on the beach near the break wall and placed all my belongings under bungees on the board since I would be getting out of the lake at a different location.  Just a tip - bring a trash bag to put your clothes and shoes in before placing them in your iSUP bag to keep them nice and dry.  You can also use a large dry bag.  I paddled at Osterman Beach for a while to enjoy the calm waters and then made my way south around the break wall.  If you don't own a paddle board, Chicago Paddle Company, rents boards at this beach and also offers SUP yoga classes!

Montrose Beach

Montrose Beach

Montrose Beach

Montrose Beach

After I paddled around the Osterman Beach break wall, the next beach I could see was Foster Beach, which is not a designated launch point.  Just past Foster Beach is Montrose Beach, which is a designated launch point!  You have the option to get out at Montrose Beach, but there is a dog park on the northwest end of the beach, so stay southeast of the dog beach.  The paddle from Osterman Beach to Montrose was gorgeous and the lake was like glass.  The water was so clear you could see the bottom - just beautiful!  

The paddle area at Montrose Beach is huge!  It's also a great place to launch and paddle for the day.  There is a protected area within the break wall that is always calm and another great place to show off your SUP yoga skills!  My goal was to paddle around the break wall south to Montrose Harbor.  As soon as I started to make my way around, the water turned rough with waves crashing into the break wall.  The rest of the paddle was like this, which is always fun and a great challenge - just make sure you have your leash and personal flotation device secured.

South of Montrose Harbor

South of Montrose Harbor

Admiring the Chicago skyline just south of Montrose Harbor

Admiring the Chicago skyline just south of Montrose Harbor

The paddle from the Montrose Beach area around the break wall to Montrose Harbor is about 1.5 miles.  You will begin to see the Chicago skyline in the distance and there is a large area to paddle before entering the harbor if you'd like to spend some time taking in the views.  Be mindful of the boats and jet skis coming in and out of the harbor, though.

The paddle from Osterman Beach to Montrose Harbor was both amazing and challenging.  I'm hoping to make it to Diversey Harbor or North Avenue Beach, eventually!  The views of the skyline are incredible and just keep getting better and better the further south you paddle.  Even if you only plan to paddle Osterman Beach, it's definitely worth the trip - I may even have to reconsider my Top 5 Stand Up Paddle Boarding Spots in Chicago!