In September 2025, the Town of Shaftsbury posted a question on its website: "Do you have a Tractor that you would like to decorate and drive for a Holiday Tractor Parade in Shaftsbury?" A second option read, "NO - But I want to help others decorate theirs."
Ten weeks later the town held its first Holiday Lighted Parade, with 33 entries. On Saturday, November 28, it does it again. Shaftsbury's newest tradition is only a year old, and the town still has no Chamber of Commerce event or long-standing institution behind it. How big it gets depends on how many neighbors sign up with something that runs and can carry a string of lights.
The doubt came before the parade
The idea came up at a Select Board meeting. Resident Art Whitman told the board that another resident had asked him about a holiday tractor parade about a month earlier. The town had already posted one survey to test interest, and according to the Bennington Banner, Whitman reported the results this way: "27 people responded. 81 percent would love to see it. 26 percent would help."
People were interested. Equipment was the problem, which is why the tractor question went up after that meeting. Whitman put it plainly to the Banner:
"I don't know that many farmers left in Shaftsbury with tractors."
He pointed across the state line to Greenwich, New York, as the model. The Banner noted that the Greater Greenwich Chamber of Commerce held its 13th annual Holiday Lighted Tractor Parade in November 2025. That parade's organizers estimate it draws about 10,000 people to watch more than 70 tractors and displays. Greenwich had more than a decade of practice behind that number. Shaftsbury had a survey with 27 responses.
What 33 entries looked like
The parade went ahead on November 29, 2025. The Holiday Lighted Parade Committee's write-up in the town's 2025 Annual Report calls it "our very own first ever Holiday Lighted Parade." The committee wrote that residents "braved the chilly temperatures and crowded the streets" to watch.
The worry about tractors resolved itself in an unexpected way. The lineup was built from whatever could be lit:
- 3 fire trucks
- Two town tractors
- A lighted lawn mower
- Single tractors
- Large farm equipment pulling Christmas-themed wagons
The committee wrote that all of it was "decorated with hundreds upon hundreds of strings of lights."
The report credits co-chairs Art Whitman and Charlie Jenks, with his wife, Gina. It also thanks the Shaftsbury Fire Department, the Bennington County Sheriff for traffic control, Dailey-Peckham LLC for letting the parade stage on its property, and Ron Jennings as the official display counter. The committee closed with: "Already people are talking about how to make this new event bigger and better! See you next year!"
So 33 entries was the whole first-year count, set against Greenwich's 70-plus after thirteen years. It also started from a town that had openly asked whether it could field enough machines at all.
The rules decide what kind of parade this is
The town's parade page lists the 2026 rules. Read together, they describe a parade built around vehicles and lights, watched from the roadside:
- Everything is lit. All vehicles must be lighted.
- One Santa. No Santa Claus costumes are allowed on entries, because the parade has exactly one Santa Claus.
- Nothing thrown. No handouts along the route.
- Wheels only. No walkers, no bicycles, and no hanging or dangling from vehicles or floats.
- Holiday music only. Entries are asked to be courteous of the floats around them.
- Adult drivers. Drivers must be at least 18 and hold a valid driver's license.
- Generators stay put. They must be secured, kept away from anything combustible, and not refueled once the parade is moving.
Those rules explain how a lawn mower can sit in the same lineup as a fire truck. The bar for entry is lights, a licensed driver and a safe setup. For a town that worried about running short of tractors, that is a wide door.
Year two, at a glance
The parade happens Saturday, November 28, 2026. It is two weeks after this post publishes and falls on Thanksgiving weekend.
| Detail | 2026 parade |
|---|---|
| Date | Saturday, November 28, 2026 |
| Lineup | 5:00 p.m. at Peckham-Dailey's, 1358 VT Route 7A |
| Kickoff | 6:00 p.m. sharp |
| Check-in | Required for entries; check in with Gina Jenks on arrival |
| Registration | Town office, town website, or Art Whitman or Charlie Jenks |
| Weather | Goes on rain or snow unless conditions are extreme |
| Updates | ShaftsburyVT.gov and the Facebook page "News from Shaftsbury Municipal Offices" |
The town office is at the municipal offices at 677 Route 7A. The registration form asks for the vehicle type, whether a trailer is attached, and how many people will ride. The trailer question is there to help with lineup order.
At the Select Board's October 19 meeting, the town reminded residents of the parade date and how to register, and said organizers are accepting donations. That makes a second way to take part for anyone who answered "no" to the tractor question last year.
Two weeks earlier, a tradition in its seventh year
Before the tractors line up on Route 7A, Shaftsbury's other holiday gathering takes place a short distance down the road. The Holiday Makers' Market runs Sunday, November 15, from 1 to 4 p.m. at the Robert Frost Stone House Museum. It is free and open to the public. Bennington College calls it the seventh annual market, "a free, festive afternoon to kick off the holiday season with music, food and drink, and incredible crafts."
The two events make a useful pair. The market has had six years to settle into a fixed spot on the calendar, with an institution behind it. Bennington College acquired the Stone House in December 2017 and runs it as the Robert Frost Stone House Museum at Bennington College. The parade is in the year a market goes through once, when the first run worked and the second decides whether it becomes routine.
The market also falls at a turning point for the house itself. The museum at 121 Historic Route 7A keeps its regular hours, 10 a.m. to 4 p.m., on weekends in May and Thursday through Monday from June through October. From November through April, the house is open by appointment only, for an additional fee, when staff is available. The grounds stay open dawn to dusk all year. Mid-November's market is one of the last easy chances to visit before the house goes quiet for winter. Questions about the market go to the museum at [email protected] or 802-447-6200.
The weeks around both dates
A few other dates fill in the late-fall calendar near Shaftsbury.
Pleasant Valley Tree Farm, at 313 Pleasant Valley Road just over the line in Bennington, lists its 2026 season starting November 14. Hours are 9 a.m. to 4 p.m. on Saturdays and Sundays, closed Thanksgiving Day, and 9 a.m. to 4 p.m. after Thanksgiving, with the fields closing at 3:30 p.m. The farm sells choose-and-cut and precut trees, plus wreaths, garland and kissing balls. That puts parade Saturday in the middle of tree season.
For produce once the farm stands close, Mighty Food Farm is a certified-organic vegetable farm at 280 Rod and Gun Club Road, now in its 20th growing season. It supplies vegetables year-round through its CSA. It also sells at the Dorset Farmers' Market on Sundays from 10 a.m. to 2 p.m. at the JK Adams warehouse, October through March. On November 15 that market and the Makers' Market fit into the same Sunday: Dorset in the morning, the Stone House in the afternoon.
Then comes the Saturday after Thanksgiving: lineup at 5, kickoff at 6. Last year's count stopped at 33 entries, and this year's total depends on how many entries register by parade night.
If the parade has you thinking about your own place in Shaftsbury or Sunderland, and what it might be worth on a market that runs on the same small-town calendar, Southern Vermont Realty Group would be glad to help. Get a Home Valuation from a team that follows these towns closely.
