Pullaro came in only five seconds behind Thomaston's Blake Fenwick after the Spartan runner was involved in a mix-up with several other harriers near the end of the 5-kilometer race.
Pullaro was among a lead pack of runners who made a slight wrong turn just before the course empties out into an open meadow for the final leg. Fenwick, who was slightly behind the lead pack, took advantage to slip into the lead as the other runners attempted to catch up. Pullaro made a valiant attempt to run down Fenwick but came up just short.
"Making the wrong turn definitely cost us all a few seconds," said Pullaro, Shepaug's number-one runner all season. "I was right in there battling for first with two kids just in front of me. If I hadn't made the wrong turn I might have been able to win."
Pullaro credited his emergence this season on the work he put in during the off-season.
"I spent the summer putting the miles in to improve. I'm happy with my performance and this was my best race of the year."
Pullaro clocked a 17:22 for a 5:36 per mile pace.
Matt Griffith placed 16th for Shepaug, Mike Piersall 22nd, Brett Burman 24th, Cody Brennan 26th, Evan Garrity 28th and Jim O'Donnell 34th.
The Shepaug boys finished fourth overall, with 90 points. Nonnewaug, with 43 points, was first, with Thomaston (73 points) in second, Litchfield (77 points) third, and Lewis Mills (128 points) fifth.
Over on the girls side, Gina DeMeo had a strong race, placing 13th in a time of 22:45.
Elsewhere for the Lady Spartans, Brooke Parker was 25th, Taryn Bartkus 36th, Nikki Parzuchowski 40th, Janine Parker 46th, Shannon Bartkus 53rd and Sarah Paisley 54th, who finished sixth among eight teams in the girls event. Thomaston easily won the team title.