Chappaqua's Train Station Is Where October Weekends Happen

This October, most of Chappaqua's weekend calendar happens in one place. Four separate groups have scheduled programming at the Chappaqua train station between now and the end of the month: the farmers market, the volunteers who run the reuse shed, the Town's sustainability board and Recreation & Parks. Every Saturday, both South Greeley Avenue entrances feed the same lot. One Sunday at the end of the month, a costume parade takes it over.

The timing matters because the season is short. The station's biggest fall event, the Chappaqua Children's Book Festival, was canceled in September. The reuse shed's season ends with October. After the Ragamuffin Parade on October 25, the station's open-air calendar thins out fast. The next few weekends are the last ones like this until spring.

Saturday Mornings Run on Two Clocks

Two operations share the lot on Saturday mornings, and they keep different hours.

The Chappaqua Farmers Market runs from 8:30 a.m. to 1 p.m. at the station. The Take It or Leave It Shed, known locally as TIOLI, sits at the first left after you enter the station parking area from South Greeley Avenue. It runs on a tighter schedule.

The Town describes TIOLI as a reusable-item "shop" run by volunteers, with no money involved. Only residents can drop items off because the shed has limited room, and anything not taken by noon has to be packed back inside it. Volunteers start packing shortly after 11, so if you shop at 11:20, expect a smaller selection than at 9:15. Shoppers may be asked to limit their time so everyone gets a turn. Children must be supervised, and no dogs are allowed.

That leaves a short window. The shed's posted season is Saturdays April through October, so the remaining Saturdays this month are its last until spring. If a closet cleanout has been waiting since summer, October is the time to do it.

What's on the market roster right now

The market's vendor list, dated October 3, is long enough that two people can shop it with no overlap.

• Fruit and produce: Caradonna Farm, Fresh Meadow Farm, Mead Orchards, Obercreek Farm, Orchard Hill Organics, Stars of the Meadow and Tivoli Mushrooms.
• Bread and baked goods: Bien Cuit, Bohemian Baked, Butter + Bow, DoughCo Bagels, Heathcote Bakery, Knot of this World Pretzels, Mayfield Farm, Noble Pies, Red Barn Bakery and Wave Hill Breads.
• Meat, dairy, fish and specialty: Chaseholm Farm, Highland Hollow Beef, Iberian Delights, Letterbox Farm, Pura Vida Fishery and R&M Farm.
• Prepared food: Bonnes Saveurs, Grumpy Dumpling, Mama Hu's Sushi Bakes, Mel's Pierogies, SMOK'D, SOUPERNATURAL, Villa Emilia Empanadas and Wild Radish.

The market also added something new this year. CULTIVATE is a table the market describes as a hub where "food, health, sustainability, and community come together," and 2026 is its pilot season. Its programming includes cooking demonstrations, crop and gardening talks, sustainability guidance, activities for families and children, and information on food access and nutrition programs, including SNAP/EBT. If you've walked past it without stopping, you'll have to get there before the outdoor season ends to see what a pilot year looks like.

October 17: The Lot Picks Up a Third Use

On Saturday, October 17, the farmers market, the shed and an EV Car Show all run at the station on the same morning. The show runs from 8:30 a.m. to noon, which matches the market's opening and the shed's hours.

The presenters are Drive Electric Westchester, the New Castle Sustainability Advisory Board, Pleasantville Climate Smart Communities and the Chappaqua Farmers Market itself. Because the market is a co-presenter, the show is built into the regular Saturday rather than running beside it.

In its September 23 notice, the Town said the board was recruiting EV and plug-in hybrid owners to display their vehicles and talk with visitors. The notice lists the vehicles planned for display so far:

• Cadillac Lyriq
• Chevy Equinox EV
• Ford Mustang Mach-E
• Polestar 2
• Rivian R2
• Tesla Model 3 and Model X
• Toyota bZ4X

Set your expectations accordingly. The event materials invite visitors to learn from owners and don't advertise test drives or a ride-and-drive. This is a morning for asking a neighbor how their car does on a winter commute, not for driving one around the block. If the Town is still looking for owners and you have one of these cars, the September notice is the place to start.

October 25: The Station's Big Fall Day

The station was supposed to host two large free events this fall. Only one is still on the calendar.

The Chappaqua Children's Book Festival was set for Saturday, September 26, from 10 a.m. to 4 p.m. at the train station, with author storytimes, illustration demos, food trucks and a Family Fun Zone. Organizers canceled it as the forecast worsened. They cited wind and travel advisories, the chance of flooding, downed trees and power outages, and advice from their tent company. The Town calendar now marks the date "CANCELLED." As of this writing, the festival's site doesn't list a makeup date or an alternate event.

That makes the Ragamuffin Parade on Sunday, October 25, the main family event at the station this fall. Recreation & Parks runs it on this schedule:

1. 12:30 p.m. Parade lineup at the Chappaqua train station
2. 1:00 p.m. Parade starts
3. Until 4:00 p.m. DJ, inflatables, crafts and activities

Costumes are encouraged. The rain date is Sunday, November 1. The Town hasn't published a route, so plan to meet at the station and follow along. After how September went, it's worth checking the Town calendar the morning of the 25th, since the parade can move to November 1.

The Rest of the Month, Off the Platform

The station doesn't hold everything. A few October events happen elsewhere, and some fit neatly around the Saturday market.

The Fright Night Rewind double features on October 10 and 11 split the films by audience. The afternoon picks suit kids, and the evening ones are for older viewers. On the 10th, you can go from the morning market to the 4 p.m. Hotel Transylvania showing without a long gap in the day.

The Be the Light bonfire is at the Recreation Field, 200 S. Greeley Avenue, the evening after the EV show. It's free and includes music, a candle-lighting ceremony, a food truck and ice cream.

The Chappaqua-Millwood Chamber of Commerce runs the Downtown Trick or Treat on Friday, October 30. It's a weekday, so it reaches families on a school-day afternoon rather than on the weekend. Participating merchants hand out candy in two windows, noon to 2 p.m. and 3 to 5 p.m. No registration is needed. Desires by Mikolay is also offering a first-come giveaway for moms while supplies last.

On South Greeley, one storefront is still unconfirmed. Green & Tonic has closed at 75 S. Greeley Avenue, and The Farm Cafe was announced as its replacement. The Farm Cafe is a smaller satellite of the Valhalla breakfast-and-lunch café, and it was aiming to open in early September. We haven't confirmed that it opened on schedule, so check before planning a post-market breakfast around it.

After October 31

The station's November calendar looks different. The TIOLI shed's posted season ends with October. The Ragamuffin Parade only comes back on November 1 if rain pushes it there. The Town calendar keeps listing the farmers market at the train station on Saturdays through December 12. The market's own site, though, doesn't announce a last outdoor date or say whether those later Saturdays are indoors or outdoors. Until the market posts its own late-season plan, treat December 12 as a calendar listing, not a confirmed outdoor date.

For now, the next three Saturdays and the Sunday parade are the last stretch of the year when one lot hosts most of what's happening in town.

Questions about how the calendar shapes a Chappaqua move? The E & F Team works with families across Chappaqua and New Castle and can help you time a listing or a home search around the town's seasons. Schedule a free consultation, and we'll walk through what the coming months could look like for you.