Where to spend S$0, S$5 and S$250 this October

Orchard Road can wait. This month's better shopping is a free pushcart market at PLQ Mall, a shop-local set-up in Thomson and an entire hall of winter gear at Singapore EXPO — plus eat-and-drink dates running from S$5 soul food to a S$250 Cantonese dinner. Here's what's worth the trip, what's worth the queue, and what to jio the group chat for.

Pushcarts by PARADE @ PLQ Mall is the no-commitment one: it runs until Thu 31 Dec 2026 at PLQ Mall, entry is Free, and the point of the carts is handmade — small businesses showing their own creations rather than the same mall-brand stock you see everywhere. Because it's a rolling run rather than a single weekend, there's no panic attached; duck in while you're already at PLQ instead of planning a whole trip around it. Best for the friend who is impossible to buy for.

Central Singapore Market @ Thomson Community Club takes over Thomson Community Club on Sat 24 Oct, with a single brief: shop local, support community. Expect a neighbourhood-scale market rather than a curated design fair — the appeal is spending with the people around you. It's an easy add-on if you're already in Thomson or Bishan, and if you're coming from the other side of the island, pair it with lunch nearby so the journey earns its keep.

Winter Time Expo Sales opens Sat 24 Oct 2026 at 10.30am in Singapore EXPO Hall 6B, and entry is Free. What's on the tables is practical rather than pretty: winter wear, luggage and travel gear, all in one hall — exactly the trio you want sorted before a cold-climate trip. It's a proper expo floor, so wear comfortable shoes and bring a bag you don't mind filling. Free entry means you can walk in, compare across stalls, and walk out if nothing fits.

Be An Expert in Champagnes Masterclass is the midweek option: Wed 14 Oct 2026, 7pm, at the Fine Wines SG Tasting Room, tickets S$136.27–229.52. It's a sit-down taste-and-learn session rather than a party, which makes it a good shout for a date who actually wants to talk, or a small group who've been meaning to do something other than dinner. Note that this is a tasting and not a meal, so plan supper afterwards.

A Winemaker's Dinner with The Cutting — Barossa Valley is the splurge: Fri 16 Oct 2026, 7pm at Asia Grand Chinese Restaurant, S$250.47 a head. Five Cantonese courses matched to Barossa Valley wines — an unusual pairing on paper, and precisely the kind of dinner you book for an occasion rather than an ordinary weeknight. Go with someone who'll split a bottle properly and linger over the last course.

Under One Roof: A Living Chinatown Experience (SG61 Bundle) runs Sat 17 Oct 2026 at 5.30pm and repeats every Saturday, 5.30pm–8pm, from the Chinatown Heritage Centre, at S$61. The format is a character-led tour followed by a heritage dinner, so you end up eating in the very neighbourhood the tour just walked you through — a far better way to remember it than reading a plaque. It's a recurring Saturday slot, so if one date is full there's always the next.

Soft Hours - Soft Landing #1 is where to point the group chat when the budget is tight: Sat 24 Oct 2026, 3.30pm at Nitty Gritty: American-Singaporean Soul Food, tickets S$5–20. It's the first of the Soft Hours Soft Landing series, with soul food and live tunes in the same room — an afternoon that rolls into evening rather than a late night. It's the smallest outlay on this list, which makes it the easy yes for a group that can never agree on a number.

Two entries here are Free to walk into — Pushcarts by PARADE @ PLQ Mall and Winter Time Expo Sales. One repeats every Saturday, one runs right through to the end of December, and a few are single dates worth choping early. Browse the free ones if you just want out of the house; book the Chinatown dinner if you want a night with a story in it.