Beloved crossing guard offers smiles and safe passage

When four-year-old Carter Ralph arrived for pre-K class on the first day of school at Woodstock Elementary School (WES) on Aug. 30, his friend — Mr. Wes the Crossing Guard — was there to greet him, fully bedecked in a pirate costume.

“Mr. Wes is my friend. He gives me gifts and toys to play with,” a bashful, soft-spoken Carter shared on Tuesday morning as he arrived at school hand-in-hand with his mother, Marianne Ralph, and older sister Ella, 6.

For two generations of WES students and their families, Wes Hennig is a beloved figure, kindly mentor, and steady friend, whether at the helm of the elementary school’s maintenance team or, since his retirement from that gig two-plus years ago after 22 years, as the jovial, grandfather-like man who, as the local crossing guard, greets students, families, and staff coming and going from WES each day of the school year. To Woodstock kids from 4 to 24, he’s known simply and affectionately by the name by which they’ve always known him:

Mr. Wes.

“He deserves to be recognized,” Principal Maggie Mills commented at the end of the school day last Friday, shortly after Wes Hennig concluded another five-days-a-week stint as the WES crossing guard along South Street just outside Woodstock Village. “He’s just such a great presence. My only hope is that he’ll keep on doing it. He certainly doesn’t need to do it, but I think he just loves to be connected to the school and the kids in some way,” Mills added. Wes Hennig’s commitment to connecting with WES children at their own level dates back two decades and more. “He was always working on projects with the kids, such as building birdhouses or working with mentees to repair furniture. He was a really important mentor for the students while he was here. He also has extensive knowledge of history, especially of Vermont during the Colonial period and the French and Indian War,” the WES principal raved.

Marianne Ralph waxes ecstatic when she talks about young Carter’s affection for Mr. Wes — and she asserts that it’s a two-way street. “I think when another adult goes above and beyond for a kid, as parents and a family, that’s something you’ll remember forever. I know that Carter will always remember it. He’s only in pre-K, but he totally clicks with Mr. Wes and loves to see him every day. It’s just such a special part of living here. Carter is young, he loves costumes and dressing up, and he always wants to bring something to show Mr. Wes each day,” Ralph enthused. “Mr. Wes will always ask, ‘What is it you have for me today, Carter? Can you show it to me?’ He’s just the sweetest man.”

One of young Carter Ralph’s prized possessions is a toy treasure chest, replete with sparkling “jewels” that Mr. Wes gave to him at the very end of the last school year. Carter acknowledged the gift anew on the first day of school in late August when he greeted Mr. Wes at his post along South Street, just outside the playground and main entrance of WES, excitedly waving a small pirate flag. “Carter was so excited to be here,” his mother recalls. “Every time you go to the school, in the morning or afternoon, it’s always, “Mr. Wes, hello, how are you?’ He knows everyone – all the kids, all the parents.” About that pirate flag Carter was sporting? Mr. Wes gave his school-crossing charge “a huge pirate flag, a Jolly Roger flag” just a few days ago.

Drawing on his innate talent, outgoing demeanor, penchant for colorful costumery rooted in his varied historic reenactor roles, and abiding love of children, Hennig considers it a special privilege to continue serving the school where he has worked for nearly a quarter of a century. “I try to make the kids happy — you know, make them smile,” Mr. Wes said against the backdrop of Tuesday’s unpredictable weather, which had the crossing guard dressed in rain gear and his mini-minions gearing up for a last-minute dash into the school before Maggie Mills took to the intercom to remind everyone that classes were about to begin. His philosophy as a crossing guard is largely the same as it was when he served on the maintenance staff at WES for more than two decades. 

Mr. Wes offered, “When I was a custodian, I knew a lot of the kids. I helped them at the bus stop and I played with them on the playground. I used to dress up back then as well.” Henning continues to play the role-playing card in his relatively new position as a crossing guard, too. “I dress up at Halloween. I play Santa at Christmas. And come St. Patrick’s Day, I sometimes dress up as a leprechaun. Back in my time in maintenance, I’d go into classrooms when nobody was there during the day and turn a few desks upside down, because leprechauns are associated with pranks.”

“It’s all about the kids,” Wes Hennig likes to say. “It is pretty scary to start school, especially on opening day, so I try to keep them from crying, help them feel more comfortable at school. I get to the point where I know the kids very well and I get to know the parents well, too. Even the parents call me Mr. Wes. It’s very respectful.” In fact, no matter where he goes in Woodstock, including to his twice-a-week, part-time stint as a stock clerk at Mac’s Market and while working as an elected constable in Barnstable, even 20-somethings who knew him as young kids still refer reverently to Wes Hennig as “Mr. Wes.”

Just before WES Principal Mills welcomed students to another day of classes over the P.A. system on a rainy Tuesday morning, a parent eyeballed Wes Hennig in his crossing guard rain gear, checked out a photographer who was taking pictures of the man at work, and quipped, “You should see him in his full regalia when he’s really dressed up.” Immediately after that, a young boy bolted over the crosswalk, passed the crossing guard, then paused curbside to catch his breath, look back and say, “Have a great day, Mr. Wes.”

The truth is that any day when Wes Hennig greets parents and children at WES, no matter the weather or time of year, is a great day indeed.