Liphook has suffered a wave of vandalism since Easter and the February half-term school holidays.
The tennis pavilion on the recreation ground and Gospel Hall in Tower Road have both been targeted in recent months.
The recreation ground is owned by Bramshott and Liphook Parish Council and damage was done to one of the gates.
Parish clerk Jane Sawyer said: “The first time the vandals came, they smashed our gates to get in and we have had to replace the gate as it was completely ruined.
“They have broken into the pavilion at least twice in the last ten days and the third time they didn't actually get in because they were chased off.
“We believe it's the same group because they've been spotted going around the village more than once.
“The last event at the tennis club pavilion was caught on CCTV and that has been passed on to the police.”
Local councillor Bill Moulland added the same group of youths were confronted after jumping off the roof of the Gospel Hall.
Hampshire Police confirmed the gate incident took place sometime between 5pm on Friday, April 5 and 8am on Monday, April 8.
The youths on the roof who were also discovered to be littering were there from 6.30pm to 7pm on Tuesday, April 9.
The T-Rex sculpture and the fence at Old Thorns Hotel & Resort had also been knocked over but it’s unknown if it was vandalism or high winds at the time.