North Side

1. Saturday, Oct 3, 1:00 PM: the festival runs 9 AM to 6 PM Saturday and Sunday Lincoln Square Ravenswood Apple Fest (39th annual), N Lincoln Ave between W Lawrence and W Sunnyside — The Lincoln Square Ravenswood Chamber of Commerce closes three blocks of Lincoln Avenue for fresh-picked apples and cider from Midwest farms, apple dishes from local restaurants, hard and non-alcoholic ciders, seasonal beers, a makers' market and live music. Saturday runs 9 AM to 6 PM, and admission is a $5 suggested donation. The chamber's own page, do312 and Chicago on the Cheap agree on the dates and hours. Coverage calls Saturday the busiest day, which is why we start at 1 PM and leave around 3:15, not later.
2. Saturday, around 3:15 PM: about 1.1 miles north and a little east The hop to Half Acre Beer Co., 2050 W Balmoral Ave — By our map math, the north end of the festival at Lawrence and Lincoln is six blocks south and about three blocks west of Half Acre. That is roughly 1.1 miles, a 25-minute walk or a five-minute ride. Walking it gets you out of the Apple Fest crowd and lands you at the party by about 3:45, just before the DJ handover at 4.
3. Saturday, Oct 3, 4:00–9:00 PM: one day only; the party runs noon to 9 Block Club Chicago's Block Party (third annual), Half Acre Beer Co., 2050 W Balmoral Ave — Block Club Chicago, the nonprofit neighborhood newsroom, runs this with Half Acre. It is free with an RSVP on the party's own site. Block Club's published schedule has DJ Cam Be from 4 to 8 PM and karaoke from 8 to 9. We arrive at 3:45 for the 4 PM DJ start; the kids' zone clears out at 5. Sunset is about 6:30 by our calculation, so you get two and a half hours of daylight before the karaoke. Block Club, Choose Chicago and the party's own site all carry the date and the noon-to-9 hours.

Why it lands: Both halves are free or close to it, so the only money you spend is on what the two of you actually want to eat and drink. The walk between them is the one quiet half hour of the day, which is where most of the talking happens. The 8 PM karaoke gives you a clear last stop. You can sing, or you can watch other people sing, and either one ends the night by 9.

Weather backup: Apple Fest also runs Sunday, October 4, from 9 to 6, and Friday the 2nd from 3 to 7. The block party is Saturday only. If Saturday does not work, Sunday at Apple Fest plus an early dinner is the smaller version of the same plan.

1. Friday, Oct 9, around 5:45 PM: two blocks from the Fullerton L Fullerton station (Red, Brown and Purple lines) to Jonquil Park — Jonquil Park is at 1001 W Wrightwood Ave. By our map math that is about two blocks north of the Fullerton stop and a few doors west, roughly a five-minute walk. Friday hours are 5 to 10 PM. Sessions are two hours, so pick your time when you buy the tickets.
2. Friday, Oct 9, a two-hour ticketed session between 5 and 10 PM Lincoln Park Wine Fest, Jonquil Park, 1001 W Wrightwood Ave — This is the festival's 10th year. General admission starts at $30 and is capped at 600 people per session. It includes 12 standard tastings from more than 50 varietals and a commemorative glass. VIP, from $67.50, adds five specialty tastings, private seating and a separate entrance. There are food pavilions on site, and proceeds go to the Wrightwood Neighbors Association, which looks after the park. The event is 21 and over. Jonquil Park, Wrightwood Neighbors and the Eventeny listing all carry the same three days and hours. Sunset is about 6:21 by our calculation, so an early session gets you the last of the daylight.

Why it lands: A tasting with a fixed number of pours takes care of both pacing and the question of when to leave. The 600-person cap per session keeps the park from feeling packed. We chose Friday because Sunday is marathon day: the course runs through the North Side on the 11th, and street closures and crowds make the festival's Sunday session the hardest one to get to.

Weather backup: Saturday, October 10, runs 11 AM to 10 PM, and an afternoon session pairs with the Chicago Art Fair's Saturday hours downtown if you start early. Sunday the 11th, 11 AM to 7 PM, is open too, but check the marathon's street closures before you go.