We had our boating outing yesterday. It was a beautiful day on the lake and the fish were biting for at least two of the three boats. Our boat got to enjoy each other's company.

I wanted to report on our food finds.
For lunch, I ended up ordering sandwiches from Dockside Subs right at the Waukegan Harbor. Mike at Dockside Subs made up a three bags of sandwiches, chips, pickle spears and cookies (one bag for each boat.) I didn't go too exotic - ham & swiss, roast beef and american, turkey and provolone. Each sub had lettuce and tomato, and mustard and mayo packets were provided on the side. The rolls used for the subs were great. I don't know what they were, but everyone loved them. The meats in the sandwiches were good quality. The pickles were good and crispy. The chocolate chip cookies didn't seem "homemade" to me, but they were a nice finish after a sub and a beverage or two.
After the fishing expedition, we ventured over to Madison Avenue at the recommendation of our boat's first mate and mentioned by Cathy2 above. I learned we wouldn't be too casual. It is a white-tablecloth restaurant, but they get a lot of business from fishermen. We really only needed a place for another beverage or two and some appetizers. The appetizers were pretty standard: jalapeno poppers, potato skins, calamari, wings, mozzarella sticks, etc. Of those listed above, I sampled a popper, some calamari and a hot wing. I was surprised at how good the calamari was. The breading was light and the calamari was very tender. The hot wings were pretty good too. There was nothing left from what we ordered, but that was more an indicator of folks needing food to balance the many beverages consumed on the boat than of high good quality.
I regretted I didn't have time to stop at Dockside Ice Cream at the harbor. I could smell the waffle cones when I walked past with the bags of sandwiches and they smelled great!
Thanks again to C2 and foodie1 for your suggestions. I was intrigued by Louie's, but our group didn't have the focus to drive too far from the harbor. I'm just glad we didn't lose anyone getting to Madison Avenue!
If I ever get up to the Waukegan Harbor again, I know where to get a good sandwich. I'm glad there were some leftovers, because I didn't have an option for fresh-caught fish dinner that night!
Dockside Deli
847.623.2080
Sandwiches, cookies, & treats
Dockside Ice Cream
847.263.1846
Ice cream cones and tasty frozen treats.
Madison Avenue Restaurant
34 North Sheridan Road
Waukegan, IL 60085-4307
847.662.6090