Lincoln Square Bike Ride: Quiet Streets to the North Branch Trail

Lincoln Square rewards a rider who stays off the arterials. The streets are quiet, the squares are small and the river is close. Use it as a neighborhood loop, or as the first leg of a ride to the forest preserves. It sits in the Routes & Trails cluster beside Lincoln Park.

The neighborhood

About 41,000 people live here, alongside more than 1,000 small and medium-sized businesses¹. In 1925 the City Council named the area Lincoln Square to honor Abraham Lincoln, and a statue followed in 1956¹. The district is bounded by Bryn Mawr and Peterson Avenues on the north, Montrose Avenue on the south, Ravenswood Avenue on the east and the Chicago River on the west¹.

The commercial heart is the meeting of Lawrence, Western and Lincoln Avenues¹. Lincoln Avenue southeast of that corner holds a wide run of restaurants and shops¹. The area is historically German, and the Square Roots Festival still celebrates that heritage in music every summer¹. Apple Fest marks the start of fall¹.

The 2013 map

In 2013 the Chicago Bike Station at Millennium Park handed out free maps of self-guided rides, and Lincoln Square was on the list beside Lincoln Park and the Lakefront². The station no longer runs rides. The route below is built from today’s streets.

The route: Welles Park north, then west

Begin at Welles Park, at the corner of Lincoln and Montrose Avenues⁵. The park covers 15.84 acres and opened in 1910⁵. It is open daily from 6:00 am to 11:00 pm⁵. The fieldhouse has an indoor pool and a fitness center and keeps its own hours, 7:00 am to 9:30 pm daily⁵.

Leg	What to know
Welles Park	Start at Lincoln and Montrose5
Leavitt greenway	Runs from Montrose (4400 N.) north to Berwyn (5300 N.)4
Cul-de-sac near Sulzer Library	The Leavitt stretch ends just south of the library4
Berteau and Cullom	Existing side-street routes, westbound and eastbound4
Leland to Rockwell	Westbound approach to the river, then north to Argyle (5000 N.)3

Streetsblog Chicago’s 2024 survey described the current project as a very short stretch joining two existing Leavitt greenway segments north of Diversey⁴.

Riding west to the river

Streetsblog Chicago laid out a family-friendly path east to west in 2021. Apart from short stretches on Lawrence, which has bike lanes, Clark and Kimball, it uses quiet side streets³. The 2021 route relied on a traffic-calmed greenway on Leland Avenue through Lincoln Square and Ravenswood, with a contraflow bike lane for two-way cycling to the river³. Westbound riders then stay on Leland to Rockwell Avenue (2600 W.), turn north to Argyle Street (5000 N.), and join the route³.

That path ends at the North Branch Trail.

The North Branch Trail

The trail winds about 20 miles from the Northwest Side of the city to the Chicago Botanic Garden in Glencoe³. The 2021 article reported the trail’s extension southeast from Devon Street and Caldwell Avenue to Foster and Kostner Avenues in North Mayfair³. The Forest Preserves list the whole system at an estimated 36.7 miles, paved and unpaved⁶. Hours are sunrise to sunset, year-round⁶. Dogs must be on a leash⁶.

For a flat first ride, the Forest Preserves point to the eight-mile paved stretch between Bunker Hill and Linne Woods⁶. The 2021 article noted that there was no obvious bike-friendly route to the southern trailhead from other parts of the city³. It also put the Lakefront Trail about five miles east and the North Shore Channel Trail about two miles east³. Read the full North Branch Trail guide before you commit to the distance.

What to see on the way

The neighborhood holds the Conrad Sulzer Regional Library, the Old Town School of Folk Music, the DANK Haus German American Cultural Center and Rosehill Cemetery¹. Berteau (4200 N.) is a good westbound side-street route and Cullom (4300 N.) an eastbound one⁴.

For a longer day, pair this ride with the Bucktown and Wicker Park ride or the full best bike rides in Chicago list.