
BRATTLEBORO — Dick DeGray is no shrinking violet. The gruff, gravel-voiced former selectboard chair was the first to speak up a decade ago when downtown merchants proposed splashing their brick-and-mortar streetscape with a pastel palette of potted flowers.
“We’re not going to do this by committee,” he recently recalled saying. “Sometimes a dictatorship works.”
And so DeGray laid down the law — first by choosing the sunshiny color of that fall’s mums, then carting a wheelbarrow up and down Main Street to plant spring pansies and summer petunias.
Ever since, the 71-year-old has awakened as early as 3 in the morning to single-handedly water nearly 200 flowering barrels, boxes and hanging baskets in a volunteer effort he calculates would cost up to $45,000 a year. But the caretaker and his alarm clock are about to unplug from it all upon his retirement this month.
“I never envisioned this when I started,” DeGray said of the local color he’s cultivated.
Nor did he imagine what he describes as downtown’s increasingly gritty flip side.
“I’m out at night on almost a daily basis, so I see the underbelly of our community,” he recently told the town selectboard.
DeGray has witnessed people dealing drugs and burglarizing businesses, spurring him to call for public safety measures at a dozen selectboard meetings in the past year and a half.
He’s also concerned about a string of closing notices for such longtime downtown landmarks as the Hotel Pharmacy after 83 years, Sam’s Outdoor Outfitters after 92 years and the former Vermont National turned Chittenden, People’s United and M&T bank after 150 years.
“No one seems to be listening,” he told the board. “I feel like I have been ignored.”
In response, local leaders thanked DeGray for his comments — then moved on without taking action.

DeGray is ready to relinquish the keys to his 300-gallon water truck to the nonprofit Downtown Brattleboro Alliance. Even so, he’s anything but retiring as he seizes an exit interview to plant a few last seeds.
DeGray, for example, is reiterating his longtime call for local government to install security cameras to supplement the police department, which is budgeted for 27 officers yet employs only 19 amid staffing shortages.
“You need to have eyes on the street,” he said. “Cameras don’t prevent crime, but they help you solve crime.”
DeGray wants the town to sell or lease its Transportation Center, a five-story downtown parking garage that has faced problems with robberies, vandalism, public alcohol and drug use, and suicides.
“We can’t place no-trespass notices on public property,” he said. “If it was in the hands of somebody else, there are a lot more things they could do than what the municipality can do.”
DeGray also is asking local leaders to meet with area legislators and the Windham County State’s Attorney’s office to discuss how to strengthen laws and find more money for alcohol and drug treatment programs.
“The behavior in the community is keeping some people away, so we have to address that someway, somehow,” he said. “I don’t believe that the town has the resources to fix this problem alone.”

This is the last year DeGray will tap up to $25,000 in public and private contributions to buy flowers from the local Rashed’s Garden Center, then plant and pamper a spring assortment in May, a summer array in June and a fall capper in September. It’s also his final chance to unearth what happens downtown in the dark hours of the night.
“When I first started, I didn’t see the activity that I see today,” he said. “Now I see alcoholism on the street, I see drug deals being made, I see people sleeping in the parks and storefront doorways or coming up asking for money. Most of these people are not bad people; they’re just in bad situations.”
DeGray recalls watering early one morning when he met a man wandering aimlessly.
“I said, ‘You want to help?’”
The man offered a hand while recounting his past problems with drinking and jail. DeGray, in turn, connected him to a downtown job.
The Brattleboro Area Chamber of Commerce expressed appreciation for such flower power by naming DeGray and his wife, Vermont Shop owner Missy Galanes, its Persons of the Year in 2020. But the green thumb doesn’t till and toil for the laurels.
“There are times when I wake up at 3 in the morning and think, ‘What the heck did I create here?’” he said. “Then by the time I finish, I see the fruits of my labor. I’ve extracted as much from working on the flowers as people have from looking at them. It’s one of the true joys of my life.”
