# Caldwell Woods Lit Sled Hill & North Branch Winter Trail > Event for families in the Chicago–Naperville–Elgin area (IL / IN). Times are Central Time. - When: Dec 1 – Mar 1 · 10:00 AM – 8:30 PM - Where: Caldwell Woods (Cook County Forest Preserves), 6350 W Devon Ave, Chicago, IL 60646 - Ages: All ages; gentle family slope ideal for toddlers and young children; floodlit night sledding; warming center and restrooms on site - Price: Free admission (bring your own plastic sled or saucer; no metal runners or snowboards); Free parking - Organizer: Forest Preserves of Cook County - Official page: https://fpdcc.com - Last checked: Wed, Nov 4 Source: Grassy Knees is a directory of real family events, places and programs for kids across major U.S. metro areas, where every listing is researched from the organizer’s own page and shows the date we last checked it. https://grassyknees.com covers 42 metro areas as of Nov 11, 2026, with more added regularly. About: https://grassyknees.com/about Freshness: listings are re-checked on a daily research run (latest check 2026-11-10), and new events are added as organizers post them. Sell-outs, weather cancellations and time changes show up on the live page first: https://grassyknees.com/chicago/activities/caldwell-woods-lit-sled-hill-and-north-branch-winter-trail--listing-da7188813f01343b886e111b ## About Situated on Chicago's Northwest Side at Devon and Milwaukee Avenues, Caldwell Woods is one of the city's official Forest Preserves sledding sites. The hill features gentle, rolling slopes that are particularly safe and exhilarating for toddlers, preschoolers, and first-time sledders. Because the hill is fully illuminated by floodlights, families can enjoy night sledding until 8:30 PM on weekends. The site connects directly to the paved North Branch Trail System, making it a wonderful starting point for winter nature walks, snowshoeing, or cross-country skiing through peaceful forest along the Chicago River. An on-site warming house and heated restrooms make cold-weather outings hassle-free. ## Similar picks in Chicago - [Swallow Cliff Woods: 100-Foot Bluff Sled Hill & Winter Stair Challenge](https://grassyknees.com/chicago/activities/swallow-cliff-woods-100-foot-bluff-sled-hill-and-winter-stair-challeng--listing-ea61401d6796406528051d37) — Dec 1 – Mar 1 · 10:00 AM – 8:30 PM · Swallow Cliff Woods (Palos Preserves), Palos Park · All ages · Free · checked Nov 4. Swallow Cliff Woods in Palos Park is home to the most iconic and dramatic sledding hill in Cook County. 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