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What would summer in Chicago be without the Lakefront Trail? Use this list to help spot some of the trail’s most iconic landmarks on the North Side.

Anthony Vazquez/Chicago Sun-Times

What’s That Building? Architectural tour of the Lakefront Trail: North Side

Hop on a bike or take a long walk along the lakefront — and use these landmarks as rest stops.

What would summer in Chicago be without its incomparable Lakefront Trail, that ribbon of pavement that runs 18 miles from end to end between the spectacular beauty of Lake Michigan and the city’s skyline, parks and lagoons?

This spectacular asset flows past so many great spots, WBEZ’s Reset needed to split its lakefront architectural guide in two. Last year, we toured the southern portion from the South Shore Cultural Center at 79th Street to the Navy Pier Flyover. We pick up on the North Side to where the trail ends at Ardmore Avenue.

Chess Pavilion

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The Chess Pavilion near North Avenue Beach.

Tyler Pasciak LaRiviere/Chicago Sun-Times

Flanked by a pair of chess pieces, king and queen, a floating roof shades more than a dozen built-in chess tables, all built in 1957. The pavilion was designed by architect Maurice Webster, the chess pieces by sculptor Boris Gilbertson and the funding to build it — $90,000 or the equivalent of $1 million today — came from Laurens Hammond, the head of the Hammond Organ Company who had played chess there many times in the past.

Boat House

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The Boat House at North Avenue Beach.

Tyler Pasciak LaRiviere/Chicago Sun-Times

With its big red chimneys, porthole windows and nautical blue-and-white motif, the structure that looks like a beached ship is one of Chicago’s most whimsical buildings. This is the second boat built here. The original, completed in 1940 as part of a Depression-era Works Progress Administration project to put a big new beach at North Avenue, was by Emanuel Buchsbaum. By the 1990s, the old building was worn out. It was demolished and replaced with a larger one that kept the nautical tradition alive. This one is by Wheeler Kearns Architects, a prolific Chicago firm.

Passerelle

Air and Water show

A crowd of people make there way across the pedestrian bridge at North Avenue during the Chicago Air and Water show in 2019.

Rick Majewski for the Chicago Sun-Times

Less than a quarter-mile north of the seemingly beached ship is an arched passerelle, or pedestrian footbridge, that was part of the same WPA effort and opened in 1940 along with the beach. It may look ordinary today, but its steel arch spanning 187 feet long was a stunner in its day. New York’s Museum of Modern Art featured the bridge in a 1940s exhibit called “Built in the USA.”

Theater on the Lake

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Theater on the Lake.

K’Von Jackson for WBEZ

Strange as it may sound now, the Prairie Style building now called Theater on the Lake was originally built as a medical facility where babies and children with tuberculosis could supposedly be healed by fresh breezes blowing in off Lake Michigan. It was called the Chicago Daily News Fund Sanitarium for Sick Babies. The tapering pillars, broad roof overhang supported by curving beams and expanses of windows are all as they were built in 1920, designed by Dwight Perkins. He was also the architect of the Café Brauer building in Lincoln Park and several zoo buildings, as well as 40 Chicago public schools, including the Prairie Style high schools Schurz in Irving Park and Bowen in South Chicago.

Charitas sculpture, outside Theater on the Lake’s south side

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Charitas.

K’Von Jackson for WBEZ

The sculpture by Ida McClelland Stout depicts a robed woman with one child on her shoulder and another cradled in her arm. It was an original accessory to the sanitarium but left and came back by a circuitous route, as described by architectural historian and blogger Julia Bachrach. Created in 1922, the work stood outside the sanitarium until the late 1930s, when it was moved out of the way for widening of the Drive. Over the ensuing decades, the sculpture spent time in storage, in the Lincoln Park Conservatory and in the Garfield Park Conservatory, Bachrach wrote.

In 2016, when the lakefront area around Fullerton was being redone, Charitas was brought back to her original site.

Chevron, just north of the Diversey Harbor Bridge

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Chevron.

K’Von Jackson for WBEZ

John Henry designed this giant blue sculpture, and his huge welded steel works made him nationally prominent before his death in 2022. Abstract and angular, this sculpture has little in common visually with Charitas, but they do share one thing: They’ve been moved around.

When Chevron, more than 40 feet tall, was first installed inside a walled front yard on Armitage Avenue in Lincoln Park in 2011, neighbors had a fit. Parts of the sculpture hung over the sidewalk, and it seemed too big for a neighborhood site. The owner, construction executive John Novak, agreed to take it down in 2013, initially in a deal to install the work at Northern Illinois University. That plan fell through, and in 2015 the sculpture landed this spot on the lakefront. A decade later, it’s still there.

A Signal of Peace and The Alarm

Two sculptures in this section, two-tenths of a mile apart, together constitute a monument of conscience about the displacement and atrocities Native Americans have suffered over the centuries.

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A Signal of Peace.

K’Von Jackson for WBEZ

A Signal of Peace, just south of Chevron, is an 1890 sculpture by Cyrus Dallin, the first of four major sculptures he made depicting Native people. Two others are still standing in Boston and Philadelphia. The fourth was a temporary piece for the St. Louis World’s Fair in 1904. Dallin was studying in Paris when he sculpted the image of a Sioux man on a horse in moccasins and a feathered headdress, holding high a staff that used to have a feather at the tip, reputedly a sign of peace. It was later displayed at the World’s Columbian Exposition in Chicago in 1893, where Judge Lambert Tree was impressed. He paid $3,000 — the equivalent of $106,000 today — and the work was installed in Lincoln Park in 1894. A Signal of Peace moved to this site in the 1920s.

For anyone who might doubt that Tree had sympathy for Native Americans, who might think this sculpture was more fetishizing of Natives, Tree’s letter to park commissioners should change their minds. He wrote the sculpture was a reminder of people whose homeland was “pilfered by the advance guard of the white” and “angered for the purpose of plundering and destroying their race.”

The Alarm, a little farther north, was completed by John J. Boyle in 1884. Originally called The Indian Family, it depicts a Native family: the man standing, the woman sitting with the child and a dog, all based on Boyle’s direct study of the Ottawa people. This is another piece whose patron was sympathetic to Native people. Martin Ryerson, who had been a fur trader in Michigan dealing with the Native Ottawa, became a lumber baron and a major investor in downtown Chicago real estate. According to the Chicago Public Art blog, Ryerson referred to the Ottawa as “my early friends” who had been displaced from Michigan and “insisted the depiction emphasized their peaceful nature.”

The Alarm stood in Lincoln Park until 1974, when it was moved to make way for a zoo expansion.

AIDS Garden Chicago

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Self-Portrait sits in the center of the AIDS Garden Chicago.

Ashlee Rezin/Chicago Sun-Times

A giant green character, easily recognized for kids of the 80s as the work of graffiti artist Keith Haring, towers over the 2.5-acre AIDS Garden Chicago, which opened three years ago as the city’s space to commemorate Chicago’s victims of the HIV/AIDS epidemic that emerged in the 1980s, and to honor the people today living with HIV.

The garden’s location is meaningful to Chicago’s LGBTQ+ community. The space sits next to the stretch of lakefront once called the Belmont Rocks, an area that, according to historian Owen Keehnen, was a haven for queer people from the 1960s to the 1990s. At a time when being out wasn’t as common, “community happened” at the Belmont Rocks, Keehnen wrote. “Relationships and friendships happened here, hook-ups, unions, memorials, sex, picnics, cookouts, dance parties, and rallies.” The jumble of limestone rocks that at the time typified Chicago’s lakefront has been replaced with a concrete revetment wall.

Kwa-Ma-Rolas pole

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Kwa-Ma-Rolas.

K’Von Jackson for WBEZ

Like the North Avenue beach house, this colorful carved monument pole topped by a thunderbird is a replica of the original. The first, installed in 1927, was carved by Native people in the northwestern U.S. and purchased by James L. Kraft, the head of Chicago’s Kraft cheese empire.

According to historian Neil Gale, Kraft bought two poles from Native carvers in 1926, shipped them to Chicago on a railroad car and put one on his northern Wisconsin estate. The other, Gale found, lay for three years on the dock of Kraft’s Streeterville factory until he donated it to the city in 1929. The work depicted the thunderbird at the top, a human below and a whale and sea creature at the bottom. Over the next six decades, the pole was attacked by carpenter ants, renovated and repainted in various ways until it eventually needed replacement. In 1986 the Kraft company commissioned a new version, carved by Tony Hunt, a Kwakwa̱ka̱’wakw tribe of Fort Rupert, British Columbia. Hunt is a descendant of George Hunt, a member of the same nation who helped bring monument poles to the World’s Fair in Chicago in 1893.

Waveland Clock Tower

Waveland Clock Tower

The Waveland Clock Tower.

Chicago Sun Times

Looking like a bit of old England dropped into Lincoln Park, the brick and stone Waveland Clock Tower was built in 1931 as part of the expansion of parkland on lakefill. Its layered arches, stone details like corner quoins contrasting with the brick and a vague suggestion of a castle tower are the work of Edwin Hill Clark. He was a prolific architect of the era, designing buildings for the zoos in Lincoln Park and Brookfield as well as in Washington, D.C., and Philadelphia. He also worked on mansions on the North Shore.

Fine as it is, the building does not look as intended. According to a 1991 Chicago Tribune article about restoration of the tower’s clocks and chimes, Annie Wolford funded the original construction, leaving $50,000 in her will to build a bell tower in memory of her husband, Jacob. (That’s about $903,000 today). She wanted the structure to look similar to one in Stockbridge, Mass., where they had enjoyed bell concerts. It doesn’t: The Stockbridge Children’s Chimes Tower, built in 1878, is all stone with a Victorian peaked top.

High-rises along the 5000 North range

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Edgewater Beach Apartments.

Tyler Pasciak LaRiviere/Chicago Sun-Times

The park and beaches along the shore are on lakefill, and some of the historical buildings immediately west used to be on the water. That’s true of the Edgewater Beach Apartments, everyone’s favorite pink building. Built in 1928 as the last in a three-building row of hotels and apartments on the shoreline, it’s the only one still standing. The water is now 800 feet and several lanes of traffic east of the building.

But another, less well-known place was also dramatically impacted by the northern extension of the lakefront park. The Saddle and Cycle Club on Foster Avenue, not very visible from the trail because it consists of a low-rise structure and tennis courts, opened its clubhouse in 1899 on a five-acre site that had more than 500 feet of lake frontage. Construction of the park on lakefill in 1931 took away the club’s lakefront, but the park district promised to build a lagoon there as a replacement. It never got built, and in 1947 the club got the land where it would have been, east of the club and west of the Drive. There’s a sidewalk, not officially part of the Lakefront Trail, that runs right across the border between club and public park.

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The Saddle & Cycle Club.

K’Von Jackson for WBEZ

Saddle & Cycle was essentially a victim of its own success: Its board had been vocal proponents of the city developing trails for horseback riding and bicycling on the lakefront.

North end of the trail at 5800 N. Ardmore Ave.

The Lakefront Trail ends at Ardmore Avenue, seven and a half miles north of the Navy Pier Flyover. But if you walk about 100 yards north until the sand runs out, you’ll get a view of a building that was television-famous in the 1970s. In the opening credits of Bob Newhart’s first hit TV series, The Bob Newhart Show, the lead characters, Bob and Emily Hartley, lived in 5901 N. Sheridan Road. Bob, played by Oak Park-born Newhart, is shown walking up to the building.

Dennis Rodkin is the residential real estate reporter for Crain’s Chicago Business and Reset’s “What’s That Building?” contributor. Follow him @Dennis_Rodkin.

K’Von Jackson is the freelance photojournalist for Reset’s “What’s That Building?” Follow him @true_chicago.

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