Cycling Routes Safe for Families and Beginners: Old Town Chi's Best Rides for Every Age

Old Town Chi has more dedicated cycling infrastructure than most residents realize. The neighborhood sits at the northern anchor of a connected trail network that stretches more than 18 miles along the lakefront, giving families and first-time riders a genuine off-street option from April through October, and increasingly through milder winter stretches too.

The timing matters. Urban speed and road safety have been under scrutiny globally this summer, with city planners in multiple jurisdictions revisiting whether 30 mph limits on residential streets adequately protect vulnerable road users. For cyclists in Old Town Chi, that debate has a very local dimension: the stretch of Clark Street between North Avenue and Armitage Avenue still sees regular conflicts between car doors and bike lanes, particularly on weekend mornings when recreational riders mix with delivery vehicles. Off-street routes aren't just more pleasant, for beginners and children, they're materially safer.

Where to Start: The Lakefront Trail and the North Branch Greenway

The Lakefront Trail is the obvious starting point for anyone new to cycling in Old Town Chi. The dedicated path runs directly east of the neighborhood, accessible via the pedestrian underpass at LaSalle Drive, and is separated from vehicle traffic for its entire length through this section. Weekend mornings before 9 a.m. are quieter; by mid-morning on a Saturday in July, the path between Oak Street Beach and North Avenue Beach can feel more like a crowded sidewalk than a cycling route, so early starts are worth the alarm.

For families who want even less foot traffic, the North Branch Trail offers a compelling alternative. The route begins near the Chicago River's North Branch just west of Old Town proper, accessible from the trail entrance near Seward Park on North Dayton Street, and runs northward through quieter corridors with tree cover and lower pedestrian density. It connects eventually to the 606 Trail system, though the 606 itself, while excellent, runs closer to Bucktown and Wicker Park and may require a short on-street connection for riders starting from Old Town.

The Old Town Triangle neighborhood is a useful staging area. Its tight grid of residential streets, particularly Crilly Court, Menomonee Street, and the blocks immediately west of Wells Street, carry very low car volumes and have long served as an informal warm-up loop for parents teaching children to ride without training wheels. No paint, no infrastructure, just low traffic and a forgiving pace.

Resources, Rentals, and Getting Ready

Divvy, the Chicago Transit Authority-affiliated bike-share program, operates docking stations at several Old Town Chi locations including the corner of North Wells Street and West Eugenie Street and at North Clark Street near the Whole Foods Market. Day passes were listed at $15 for unlimited 3-hour rides as of the 2025 season; the 2026 pricing structure was not confirmed at press time, so check the Divvy app or website before heading out. Classic Divvy bikes are heavy but stable, genuinely forgiving for adults returning to cycling after years away.

The Chainlink, a Chicago-based cycling advocacy community with an active online forum, maintains crowd-sourced route recommendations updated regularly by local members. Their beginner-friendly route threads for the North Side are worth twenty minutes of reading before a first family outing. The Chicago Department of Transportation's cycling map, available as a free PDF download from the CDOT website, marks bike lanes, protected lanes, and off-street paths by comfort level, the color-coded system is accurate and useful.

One practical number: helmets are not legally required for adults in Illinois, but they are required for riders under age 16 under state law. Families with mixed-age groups should equip everyone regardless. Several Old Town sporting goods shops on North Avenue stock helmets in the $35 to $90 range.

The practical advice is simple. Pick a weekday morning, start at the Lakefront Trail entrance at LaSalle Drive, ride south to Navy Pier and back, and you will have covered roughly five miles on a fully separated path with almost no decisions to make. That's the right first ride. Build from there.