For me, fair season is the beginning of fall. I’m a true Connecticut native, and between now and mid-October there’s a fair within a short drive almost every weekend. I’ll say it plainly: I can’t resist a deep fried Oreo! The animals are probably my favorite part, though. I’m a cat mom of four rescues, and I’m the biggest sucker for every animal barn on the grounds.
I also know the other side of the counter. I’ve worked in both retail and food service, so I know what a long weekend shift feels like while everyone else is out having fun. Now, after 13 years in HR, I think about the people in those booths and the owners who send them. If your business has a booth this fall, or you’re planning a team day at the fair, here’s what I’d think through first.
Your fair-season checklist
Is travel time paid time? A normal commute is unpaid, and travel to a special assignment in another town usually is paid, minus the time the employee would normally spend commuting. If the trip keeps someone away overnight, travel during their normal working hours counts as work time, and that includes the same hours on a Saturday or Sunday.
Who covers gas, parking and meals? In Connecticut, the employer has to cover travel expenses whenever leaving them with the employee would push that person’s pay below minimum wage. Mileage rates are a good question for your CPA.
What happens if rain closes the booth early? Connecticut has a minimum-pay rule for that. Under the retail (mercantile) wage order, an employee who reports for duty gets at least four hours' pay at their regular rate. Under the restaurant wage order, an employee who reports as scheduled, and was not told the day before not to come in, gets at least two hours at minimum wage. Other industries have their own wage orders, so check which one fits yours.
Is a break built into the schedule? Connecticut requires a 30-minute meal break for anyone working seven and a half or more consecutive hours. It must come after the first two hours and before the last two.
Are you counting every hour? Every hour counts toward 40 in a workweek, and that includes travel and setup time. If you think a seasonal, amusement or restaurant exemption might apply, ask before you rely on it. Those exemptions are narrower and more technical than they sound.
Are teens working the booth? Connecticut requires working papers before a minor starts work. During school weeks, 16- and 17-year-olds are limited to 6 hours on a school day and 32 hours a week, and 14- and 15-year-olds generally cannot work in food service. Connecticut’s limits differ depending on whether the booth counts as retail or food service, so find out which one yours is before you build the schedule.
Is the team outing work? Federal rules for meetings and training treat an event as unpaid only when it falls outside work hours, is truly voluntary, has nothing to do with the job, and involves no work. That makes a good test to borrow for a team outing. If the outing is expected, happens on the clock, or has people handing out swag, plan to pay for the time. Two reasonable owners could land differently on a purely social day: keeping it truly optional and off the clock can work, and paying for the time takes the guesswork out of it. On the tax side, the IRS lists occasional tickets and occasional employee parties or picnics as benefits too small to tax. Cash and gift cards are always taxable, however small the amount.
Does your harassment policy come along? Check whether your policy says it applies at off-site work events, including a team day at the fair. Connecticut employers with three or more employees must provide two hours of sexual harassment prevention training, and new hires must complete it within six months.
Sending your employee over state lines?
If your booth is over the Massachusetts line, or in New York or Rhode Island, each state has a few rules worth knowing before you pack the van.
Massachusetts
Massachusetts requires out-of-state employers operating there to carry workers’ compensation for everyone working in the state, whatever the headcount or hours. Your Connecticut policy may already cover it, and one call to your broker will tell you.
Massachusetts requires a 30-minute meal break for anyone working more than six hours, a lower threshold than Connecticut’s. A seven-hour shift can be fine in one state and not in the other. In Massachusetts, an employee scheduled for three or more hours who is sent home early must be paid for at least three hours at minimum wage, and charitable organizations are the exception.
Here’s some good news: Massachusetts earned sick time follows the employee’s primary place of work, and a short fair assignment does not move a Connecticut employee’s primary workplace. Anyone under 18 working in Massachusetts needs a Massachusetts work permit, and that includes teens who live out of state.
New York
New York looks back at the previous year for workers’ compensation. If your employees were in New York for 25 or more individual employee-days (five people for five days adds up to 25), New York expects a full New York policy. Ask your broker whether New York appears on your policy’s information page, and where.
New York’s tax law has no minimum number of days before withholding applies. The Tax Department does have a long-standing policy for short trips. If an employee based outside New York is expected to work there 14 days or fewer in the year, and actually does, the department will not pursue the employer for skipping New York withholding. Any part of a day counts as a full day, and some kinds of pay do not qualify. That’s a conversation for your CPA before the trip.
In New York, a shift that starts before 11 a.m. and runs past 7 p.m. comes with a second meal period of at least 20 minutes between 5 and 7 p.m. New York also requires annual sexual harassment prevention training at every employer, whatever its size, and the state says anyone who works part of their time in New York needs it, even if they are based in another state.
Rhode Island
Rhode Island still has Sunday and holiday premium pay of time and a half for many workers, and for many of them Sunday work has to be voluntary. Restaurants, hotels and recreational facilities are among the exceptions, so find out which side your booth falls on.
If a Rhode Island employee reports for a shift and gets less than three hours of work, Rhode Island requires pay of at least three times their regular hourly rate, which works out to three hours of pay. A shorter shift is allowed only when both sides agree to it voluntarily. Rhode Island also requires a 20-minute meal break within a six-hour shift and 30 minutes within an eight-hour shift. Employers with fewer than three people on a shift at the worksite are exempt.
Do local minimum wages apply?
Connecticut’s 2026 minimum wage of $16.94 is already higher than Massachusetts ($15.00), Rhode Island ($16.00) and most of New York ($16.00). New York City, Long Island and Westchester are the exceptions at $17.00, so hours worked there need at least that rate.
There are no city minimum wages to track down in Rhode Island, because state law bars cities and towns from setting their own. New York’s higher downstate rates come from state law as well. The city “living wage” laws in Boston and New York City apply to city contractors and businesses receiving certain city assistance.
One thing to do Monday morning
Most owners are probably fine on most of this. Pick the one event on your fall calendar that crosses a state line, and before the gates open, make one call and send one email. Call your insurance broker and ask whether that state appears on your workers’ comp information page and whether your policy extends to an employee injured out of state. Then email your CPA and ask about withholding for the days your team will work there. Then go enjoy the fair, and save me a deep fried Oreo!
Local fairs in the region
If you’re looking for a fair to visit this fall, with or without a booth, these lists are a great place to start.
Connecticut
Association of Connecticut Fairs, member event calendar (major, district, 4-H and grange fairs statewide)
Massachusetts
Rhode Island
Meet Me at the Fair, Rhode Island fairs and festivals calendar (Rhode Island’s big agricultural fairs run in summer, so the fall listings are mostly harvest festivals.)