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 chamber closes three blocks of Lincoln Avenue for fresh-picked Midwest apples and cider, apple dishes from local restaurants, hard and non-alcoholic ciders, seasonal beers, a makers' market and live music. Saturday, 9 AM to 6 PM, $5 suggested donation. Saturday is the busiest day, so arrive at 1 and leave by 3:15.
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 — From Lawrence and Lincoln it's six blocks north and about three east: roughly 1.1 miles, a 25-minute walk or a five-minute ride. Walk it. You shed the crowd and arrive about 3:45, just before the 4 PM DJ handover.
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 it with Half Acre; free with an RSVP on the party's site. DJ Cam Be spins 4 to 8, karaoke runs 8 to 9, and the kids' zone clears out at 5. Sunset is about 6:30, so you get two and a half hours of daylight before the mic opens.

Why it lands: Both halves are free or nearly so, which means the money goes only to what you two actually want to eat and drink. The walk between them is the one quiet half hour of the day, and that's where the talking happens. Karaoke at 8 is a clear last stop: sing or watch, and either way you're done by 9.

Weather backup: Apple Fest also runs Friday the 2nd, 3 to 7, and Sunday, October 4, 9 to 6; the block party is Saturday only. Can't do Saturday? 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, 1001 W Wrightwood Ave, is about two blocks north of the Fullerton stop and a few doors west, a five-minute walk. Friday runs 5 to 10 PM in two-hour sessions; pick yours when you buy.
2. Friday, Oct 9, a two-hour ticketed session between 5 and 10 PM Lincoln Park Wine Fest, Jonquil Park, 1001 W Wrightwood Ave — GA from $30, capped at 600 per session: 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. Food pavilions on site; proceeds go to the Wrightwood Neighbors Association, which looks after the park. 21 and over. Sunset is about 6:21, so an early session catches the last daylight.

Why it lands: A fixed number of pours handles both pacing and the question of when to leave, and the 600-person cap keeps the park from feeling packed. Friday is deliberate: Sunday the 11th is the marathon, and its North Side course makes that day's session the hardest to reach.

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