In 1997 the Pumpkin Lady made her first appearance in front of Old Greenwich School, and it happened at night. Neighbors came in costume, a smoke machine supplied the atmosphere, and the unveiling turned into a Halloween party for the whole neighborhood. "It was really fun," former OGS parent Mary Jay told Greenwich Time. "We had more fun than the kids."
Her 2026 look will be unveiled tomorrow, Tuesday, October 6, from 2:30 to 4 p.m. on the school plaza at 285 Sound Beach Avenue. That reveal opens a stretch running to the first Saturday of December, and nearly every fixture in it is built, staffed, or paid for by a volunteer group. The town's main contribution over the same weeks is a short list of dates when its own rules stop applying.
A Plywood Figure, Rebuilt Every Year
The Pumpkin Lady started as a parent's vacation souvenir. Bill and Barbara Kelly, both Old Greenwich residents, saw a display of pumpkin-headed ghosts while visiting California. When Bill Kelly was named chair of the school's Pumpkin Patch in 1997, he proposed a sculpture modeled on what they had seen. Former OGS parent Cheryle Janelli designed it.
She stands about 10 feet tall and is built mostly of plywood and chicken wire, a cylinder with two long, thin arms. Over the years she has been a pirate, a hippie, a witch, a sheriff, and, in 2024, a country singer in the Taylor Swift mold. Last year the students voted on the theme. "Spooky" won with 96 votes over "sporty" with 78, and costume designer Cecilia Piszak made her a werewolf caught mid-transformation. She became a science teacher named Pumpkinia Wolff, complete with a teacher badge and a chalkboard showing the phases of the moon. Piszak had already built a new head the year before out of PVC pipe, chicken wire, zip ties, and duct tape. "It's all very MacGyver'ed together," she said.
Katie Witten, vice president of the school PTA, explained why a school project became a fixture of the village:
"It's out in the front of the school so it's kind of part of the community."
The Fair She Was Built to Promote
The Pumpkin Lady was always meant to build excitement for something larger. The 56th annual OGS Pumpkin Patch is Saturday, October 17, from 11 a.m. to 4 p.m., and the PTA calls it its largest fundraiser of the year.
The fair is older than the sculpture by about a quarter century. According to a 2015 history in the Greenwich Sentinel, a PTA pumpkin sale and harvest fair had become the "Pumpkin Patch Party" by the early 1970s. Early chairs Jane Greene and Eleanor Fitchner raised enough to pay for the school's playground. The chili came a few years later. In the mid-1970s, Happy Pappas, Mary Pilder, Joan Felicella, and others started bringing homemade chili as a hot-dog topping, and before long it was sold by the bowl.
Last year's co-chair Courtney Van Naarden described the scale to Patch: "We don't have huge roller coasters or rides. It's very much a traditional, old school festival that feels like you're at an orchard or somewhere with your family." The 2025 fair had a hay maze, pumpkin picking, crafts, face painting, food trucks, and live performances. The PTA says 2026 adds live entertainment, a Grit Ninja obstacle course, a petting zoo, and new inflatables.
The staffing plan shows how much of the day runs on volunteers. This year's co-chairs, Cindy Palmer and Emily Kaplan, have a committee that has been planning all year, and the PTA asks every family to sign up for at least one shift. A separate bake sale runs on donated homemade and store-bought items, with an allergy-safe section. The PTA called the 2025 fair a "record-breaking success."
Purple Week, Running Now
Purple Week is a smaller version of the same arrangement, and it's happening on Sound Beach Avenue this week. The town proclaimed October 3 through 10 Paint Old Greenwich Purple Week, for Alzheimer's awareness. The programming comes from businesses and a library. There are classes at Kaia Yoga and OG Yoga, an event at Perrot Memorial Library, a caregiver program at Athena Books, "Shopping and Spritzes" at Fred Boutique, and purple drink specials at participating restaurants. The town issued the proclamation, and the village supplied everything on the schedule.
November 1, When the Town's Rules Switch Off
At Greenwich Point the pattern shows up as a calendar of rules lifting. The town's OnePass page says tickets or valid passes are required at Greenwich Point and Byram Park from May 1 through October 31. Halloween this year falls on a Saturday, so Sunday, November 1 is the first day you can drive in with no pass at all. During the season, a OnePass holder bringing an out-of-town car has two options: buy a seasonal resident vehicle pass, or pay $40 for a single-entry vehicle ticket each visit. After October, neither is needed.
The off-season at the Point unfolds in stages:
- November 1. Pass and ticket requirements end at Greenwich Point and Byram Park.
- Mid-November. Safe Roads Sundays usually begin. Last season they ran every Sunday from November 23 to April 12, 8 to 11 a.m. Dates for 2026–27 haven't been posted yet.
- December 1. Leashed dogs are allowed through March 31. Leashes must be under 10 feet and held by an adult anywhere in the park. Dogs need a valid license and rabies tag on the collar or harness, and owners must pick up after them promptly.
Safe Roads Sundays look like a town program, since Greenwich Parks and Recreation staffs the checkpoint just past the main parking lot and turns away non-essential vehicles. The sponsor, though, is the Friends of Greenwich Point, which says its members and donors pay for it. During those hours the main loop road is reserved for walkers, joggers, strollers, and cyclists. Emergency vehicles, boat owners, handicapped drivers, and park employees can still use every road, and they have the right-of-way. The program is not new. A Friends of Greenwich Point newsletter from winter 2018 described that season as its 18th, which puts the start around 2001.
The same group spent last Saturday morning planting native trees and shrubs at the first dune near the entrance gate.
Who Supplies What This Season
Lined up by date, the season shows who does the work:
| Date | Fixture | Built, run, or paid for by | Town's role |
|---|---|---|---|
| Oct 3–10 | Paint Old Greenwich Purple Week | Village businesses and Perrot Memorial Library | Proclamation |
| Oct 6 | Pumpkin Lady unveiling | OGS PTA volunteers | None listed |
| Oct 17 | 56th OGS Pumpkin Patch | OGS PTA, co-chairs and family shifts | None listed |
| Nov 1 | Pass-free Greenwich Point | n/a | Seasonal pass window ends |
| Mid-Nov to mid-Apr | Safe Roads Sundays | Friends of Greenwich Point | Parks and Recreation staffs the checkpoint |
| Dec 1 | Leashed dogs at the Point | n/a | Seasonal dog window opens |
| First Saturday of Dec | First Light | Old Greenwich Merchants Association | Road closures |
The same split shows up at a larger scale in the Chimes Building at Greenwich Point. The Greenwich Point Conservancy plans to dedicate the circa-1896 building as the Daniel J. Donahue Water Sports & Recreation Center. Its plans include ADA-compliant restrooms, a new roof, restoration of the rare c.1901 chimes mechanism and bells, and a water safety center with the Emily Catherine Fedorko Foundation. In June, town budget minutes split the costs this way: the town pays for septic and electrical work, and the Conservancy pays for the chimes and related work. The minutes say the project had been delayed by negotiations over the gift agreement, and that those negotiations were nearing completion. A $325,000 town carry-forward was approved. Tod's Point Sailing School will not have to relocate during construction.
First Light, and the Merchants' Clock
The season ends on Sound Beach Avenue with the merchants in charge. The Old Greenwich Merchants Association describes itself as a not-for-profit group of retailers run by store and business owners who volunteer their time. More than fifteen years ago, its volunteers installed the clock on Sound Beach Avenue, paid for with calendar sales and contributions from shopkeepers and neighbors, and OGMA still maintains it. The group's past events have included block parties, bed races, pumpkin painting, and sidewalk sales.
First Light is held on the first Saturday of December, which this year is December 5. OGMA hasn't announced the 2026 edition yet. The association's own page gives the hours as 6 to 9 p.m., but last year's event on December 6 ran from 5 to 8, according to Patch. Check the hours closer to the date. In 2025 OGMA brought a large tree from Sam Bridge Nursery to the Old Greenwich Fire House, and the Cos Cob Volunteer Fire Company supplied antique fire trucks. Sound Beach Avenue and parts of West End Avenue and Arcadia Road were closed from 4 p.m. for setup until 9 p.m. for cleanup.
The 2024 event was the 25th First Light. Willa Koch lit the tree in front of the Sound Beach fire house, the Sound Beach Community Band played, and participating shops handed out refreshments.
The run from the plaza at 285 Sound Beach Avenue to the fire house tree is about two months, and almost every stop along the way is staffed by people who signed up for a shift.
If you're thinking about how your home's story fits into an Old Greenwich season like this one, from the Pumpkin Lady to First Light, Nora Giovati knows this calendar firsthand and is glad to talk it through. Show me homes or list my property: contact Nora today.
