A Tale of Two Ports

Point your compass to northeastern Illinois, just below the Wisconsin state border along the Lake Michigan shores. The ports of Waukegan and Winthrop Harbor boast histories extending back to the days of fur traders, canoes laden with goods, settlers, Native American tribes and the trails they made.

As people came in, so did the commerce opportunities and growth. These days, look for a mix of the old and new — while the main draw is still the water.

Waukegan

Waukegan was founded in 1859 and known as “Little Fort,” in deference to the larger Fort Dearborn, south in Chicago. The lakefront was the lifeblood for traders and fishing. By the early 1900s, high atop a bluff, a bustling downtown grew to become the center of Lake County’s economy. The lakefront and harbor areas were always a constant attraction for recreation and commerce, and continue to be.

Today, the compact harbor area offers walking-distance amenities for long-term summer mooring or day launches. Getting there is easy for a boat and trailer. Just take the Grand Avenue Bridge east to Pershing Avenue, go down the hill to Clayton or Madison streets, and turn into the harbor area. The Waukegan Port District has commercial docks, and the activity centers around the intersection at Harbor Avenue and Madison Street.

With the serene Siver Park nearby, a kitty-corner cul-de-sac has Dockside Dogs and the attached Dockside Ice Cream. Picnic tables are scattered around, and Dockside Deli is right across the street.

A large white building houses several businesses, including Perfect Imperfection charter and marine services, Harbor Canvas for sail repair and manufacturing, and TowBoatU.S. Around the back, you’ll find the self-pay day launch ramps. Nearby is Bay Marine’s new state-of-the-art facility, rebuilt after a fire in February 2022. This space provides offices, boat sales, service and storage.

The Waukegan Harbor and Marina operates the day launches and 641 slips, between the north and south harbors. They offer a full-service pier, 24-hour security and shuttle service from the parking lot to your boat. According to Robert Allan Kutzler, operations manager for Waukegan Harbor, many updates are completed, with more underway. There is a new fuel tank and updated laundry room, plus fiber optics are being installed and upgraded. Dividing the harbor is the famed Waukegan Lighthouse, built in 1899, with an extended pier and fog horn, which is open to tour.

Larsen Marine is on Sea Horse Drive, a one-mile-long roadway leading to the Waukegan Municipal Beach.

“Basically, anything that can go wrong with a boat, we repair,” says Richard Von Helms, an associate at Larsen Marine.

The Waukegan Municipal Beach and North Beach cover 400 acres and include some of the only remaining natural sand dunes in Illinois. The beach is one mile long and is groomed for one thing: Swimming. Soaking up the wind and sun also provides fishing opportunities for anglers trying to hook perch or salmon.

Causal diving and investigating shipwreck sites is a popular sport, and Lake Villa’s Toucan Dive charters excursions out of the Waukegan Harbor. Many World War II training planes from the local navy and air force bases that used the lake for practice lie beneath the waves. There is also the recently discovered wreck of the S.S. Wisconsin, an iron hull passenger and freight steamer that sank off the harbor in 1929.

If you’re searching for other entertainment, retrace your path to the Grand Avenue Bridge, and stroll a few blocks to Genesee Street, the heart of Waukegan’s business district. Walk south and attend a show at the “Grand Ol’ Dame of the Downtown,” the historic Genesee Theater. National touring acts now grace the stage of the town’s only vaudeville house and movie theater still standing.

Across the street, tip your hat to Jack Benny, Waukegan’s favorite son, in a familiar “Well” pose immortalized with a bronze statue at a park square.

Keep walking down the street and there’s La Opera, Three Brothers Theatre (a small stage venue), The Tap Room, and Mama Jerk N’ Tings Caribbean food. At Water Street, find the Green Town Tavern. “Green Town” is really Waukegan, as depicted in “Dandelion Wine,” a novel of memories by another native son, Ray Bradbury.

Returning to the harbor, stop at Sheridan Road and Washington Street to see the granite edifice of The Carnegie Library, erected in 1903. It was the Waukegan Public Library until 1965 and was frequented by Bradbury. The stone exterior is unique — it’s the only such library built into a hillside bluff.

You can walk down the hill to the Metra Station, easily cross the tracks, and return to the harbor. There is much more to discover at the city’s website (waukeganil.gov).