Krissy Blake | September 26, 2025
Fall is here, and Greenwich is packed with family fun! From pumpkin patches and fall festivals to spooky (but sweet) Halloween happenings, there’s something for everyone this October. Whether you’re looking for beloved local traditions or seasonal outings here are the highlights you won’t want to miss:
Fri Oct 3 – Greenwich Library Opening Night Celebration · 7:00 pm · Greenwich Library · Fundraiser with Music from the Sole.
Sat Oct 4 – Arch in Bloom “Pumpkins & Pints” · 12:00–6:00 pm · Arch in Bloom, Greenwich · Haunted house, pumpkin décor, family activities & fall drinks.
Sun Oct 12 – Walk/Run for Abilis (20th Annual) · 9:00 am · Clambake Area, Tod’s Point · Family-friendly 1-mile walk & 5K run.
Sat Oct 18 – Old Greenwich School Pumpkin Patch (55th Anniversary) · 11:00 am–4:00 pm · Old Greenwich School · Beloved fall festival with rides, food & games.
Sun Oct 19 – Go Wild! Family Field Day (Greenwich Land Trust) · 2:00–5:30 pm · Greenwich Land Trust Preserve · Popular family event with activities & picnic fun. Grab your tickets here
Thu Oct 23 – Breast Cancer Alliance Luncheon & Fashion Show · 11:00 am–2:00 pm · Hyatt Regency, Old Greenwich.
Fri Oct 24 – Halloween Happenings (Town of Greenwich) · Sessions at 5:30 & 7:00 pm · Bendheim Western Greenwich Civic Center · Costume contest, “Dracula’s Den,” games & candy. Grab your tickets here.
Sun Oct 26 – Ghouls in the Garden · 4:30–6:30 pm · Greenwich Botanical Center · Haunted hike, crafts, interactive performers & costume parade. Grab your tickets here
Tue Oct 28 – Perrot Walks: Tod’s Point · 9:30–11:00 am · Tod’s Point · Stroller-friendly fall walk.
Thu Oct 30 – Cos Cob Library Storytime (Special Halloween Edition) · 10:00 am · Cos Cob Library.
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