Port Washington, WI
This small town is on Lake Michigan and has a lot to offer.  It is worth the walk in the downtown area to explore the different shops and restaurants there.  There is plenty to do within a short drive from here, so it is a good stopping point for anyone wanting to spend time along the lake shore.  We stayed at the The Harborview hotel and it is located right downtown on the water.  They have a waterfront dining option, or you can easily walk somewhere down the main street to eat. There is also a waterfront walk out to the lighthouse. Grab some ice cream from the food truck or some caffeine from the coffee shop and wander the waterfront walk. A cute little town in Wisconsin that is worth a stop.  
Address: 
​The Harborview
135 E Grand Ave
Port Washington, WI 53074

Cordwalk-Boardwalk Trail
Full disclosure - we never got to hiking here.  My kids saw the lake, and all they wanted to do was swim.  This is a very popular park, and often has to close on the weekends because of the crowds.  If we would have hiked, I would have taken the easy 3 mile hike along the Cordwalk-Boardwalk Trail. This trail takes you along the shores and sand dunes next to Lake Michigan.  We come here in the summer, but mostly it is to swim in the clear and shallow water along the beach.  Currents can be a problem here, so be safe in the water.  The park does require a fee to enter $8 (out-of-state $11) for a day pass or an annual sticker for $28 (out-of-state $38).  There is also camping here, among other outdoor activities.  
Address: 
1020 Beach Park Ln
​Sheboygan, WI 53081

Pebble Beach and Pierhead Lighthouse
This easy 2.5 mile loop takes you along Lake Michigan, in downtown Milwaukee, next to the fairgrounds.  There are many places to stop and take in the sights, fish, or jog along the well maintained trail.  This is a great place to move around outside if you are exploring some of the attractions Milwaukee has to offer.  Or you can head a short distance up the shore and find a beach to swim at after the day has warmed up.  The park does require an entrance fee of $8 (out-of-state $11) per vehicle for a day-use pass or an annual pass for $28 (out-of-state $38).
Address: 
500 N Harbor Drive
​Milwaukee, WI 53202