CHICAGO — A summer stroll or bike ride along Chicago’s Lakefront Trail offers more than just scenic views — it’s a walking architectural museum. A recent feature by WBEZ Chicago maps out notable North Side landmarks along the 18-mile path between Lake Michigan and the city’s skyline, highlighting decades of design history.
Here’s a breakdown of some standout structures and sculptures that define the North Side section of the trail — perfect for locals and visitors looking to explore beyond the beaches.
Chess Pavilion: A Game With A View
Just off North Avenue Beach, the Chess Pavilion stands out with its dramatic floating roof and built-in chess tables. Designed in 1957 by Maurice Webster and funded by Hammond Organ Company founder Laurens Hammond, the space blends mid-century modernism with community spirit. Sculptor Boris Gilbertson crafted the giant chess pieces that flank the entrance.
Boat House At North Avenue Beach: Nautical Whimsy
This eye-catching structure, redesigned by Wheeler Kearns Architects in the 1990s, mimics a beached ship. Its red chimneys and porthole-style windows continue the tradition set by the original 1940 building, part of a Works Progress Administration (WPA) initiative.
Passerelle Bridge: Steel Beauty From 1940
A short distance north is the arched pedestrian bridge known as the Passerelle, a 1940 steel structure also born of the WPA era. It was even featured in a MoMA exhibit titled “Built in the USA.”
Theater On The Lake: From Healing Center To Performance Hub
Originally a 1920 sanitarium for children with tuberculosis, this Prairie Style building by Dwight Perkins has morphed into a celebrated theater. Its ornate design — tapering pillars, wide overhangs, and expansive windows — remains intact. A restored 1922 sculpture, Charitas, now graces its grounds.
Chevron: Giant Sculpture With A Controversial Past
John Henry’s bold blue sculpture, more than 40 feet tall, now resides north of Diversey Harbor. Originally installed in Lincoln Park in 2011, neighborhood pushback led to its relocation near the lakefront in 2015.
A Signal Of Peace & The Alarm: Tributes To Native Communities
These two 19th-century sculptures, located just north of the trail’s midpoint, reflect on the painful history of Native American displacement. A Signal of Peace (1890) by Cyrus Dallin and The Alarm (1884) by John J. Boyle are reminders of historic injustice, but also show the city’s evolving public art conscience.
AIDS Garden Chicago: Memory And Celebration
At Belmont Harbor, the AIDS Garden Chicago — anchored by a towering Keith Haring “Self-Portrait” sculpture — commemorates those lost to HIV/AIDS and celebrates queer community life along the former Belmont Rocks, once a vibrant LGBTQ+ gathering space.
Kwa-Ma-Rolas Pole: Native Craft With Chicago Ties
A replica totem pole near the shoreline is rooted in history dating back to 1927. Originally purchased by Kraft Foods founder James L. Kraft, the pole was later replaced by a version carved by British Columbia artist Tony Hunt in 1986.
Waveland Clock Tower: A Touch Of English Charm
Constructed in 1931, the Waveland Clock Tower resembles a piece of English countryside. Designed by Edwin Hill Clark, it was commissioned by Annie Wolford in memory of her husband, reflecting both love and architectural ambition.
Edgewater Beach Apartments: The Last Pink Giant
Built in 1928, the bright pink Edgewater Beach Apartments once stood at the water’s edge. Today, it’s 800 feet from the shoreline due to parkland development. It’s the lone survivor of what was once a luxury hotel row.
Saddle & Cycle Club: Lost Lagoon, Enduring Legacy
Founded in 1899 with prime lake frontage, the Saddle & Cycle Club lost its beach access during 1931 lakefill projects. Though promised a replacement lagoon, the land remained unfilled until 1947. The club still exists, separated from the trail by a thin park strip.
5901 N. Sheridan: Bob Newhart’s TV Home
The northernmost stretch of the trail ends near this residential high-rise made famous by The Bob Newhart Show. In the show’s opening credits, Bob is seen walking into 5901 N. Sheridan — a little TV trivia for your next walk.
Have a favorite building along the Lakefront Trail? Tell us about your favorite summer spots or hidden gems on the North Side at ChicagoSuburbanFamily.com.
