North Avenue Beach at Sunset, Then a 1958 Dive Bar on North Avenue

The park district keeps the sand open from 6 am to 11 pm, but the 2026 swim season ended on Labor Day: no lifeguards, and swimming is strictly prohibited until Memorial Day weekend. The volleyball nets in the photo are a summer frame; by November the courts are bare and the sand is empty. From this beach the sun goes down inland to the southwest, over Lincoln Park and the Old Town rooftops, not into Lake Michigan; an hour later the Loop skyline to the south lights up across the water. Check the sunset time for your date: 4:44 pm on Nov 1, 4:19 pm in the first week of December, 6:57 pm by Mar 15. Arrive 30 minutes before it. Official info: Chicago Park District beach page, checked Oct 29.

Old Town Ale House has poured since 1958. In 1971, after a fire damaged the original location, regulars helped carry the bar itself across North Avenue to its current home, and the room has stayed stubbornly the same since. Chicago artist Bruce Elliott's portraits of regulars, politicians and celebrities cover the walls. Roger Ebert called it the best bar in the world that I know about. Doors open at 3 pm and close at 4 am, 5 am on Saturday. Bring cash; the ATM inside is the only backup.

Leave the sand at the south end, by the North Avenue underpass, and walk west on North Avenue. It is about 1 km and 14 minutes at an easy pace; from the beach house at the north end, allow 20. A lake wind makes it feel longer, so dress for the walk, not the bar. Bus 72 runs the same street and stops a block from the door, and the Brown Line at Sedgwick is about a 7-minute walk. Two hours covers the light and the first pour, then you ride home warm.