The idea of a regularly scheduled meetup has been thrown around quite a bit, starting with weekly to bi-weekly, and now, monthly. So, I think it would be possible to handle two meetups a month: one that's routine, and one "special" to accommodate for any bigger events happening.
This particular routine meetup will be going to a bowling alley to play a couple of games. Right now, the intended location is going to be the Brunswick Colony Lanes in Wallingford. The website for the place is claiming that for Saturdays (if that's the ultimately decided day), until 6pm, it will cost $4 per person, per game, plus another $4 for shoe rental. However, past experience tells me that they will ask each person to fork over at least $20 for two full games. There's a pizza restaurant in the same plaza, and, with it being in between North Haven and Wallingford, there's plenty of lunch options on either end of Route 5.
I'll leave the link to the pricing page in case you want to do this on a different day: http://www.bowlbrunswick.com/hours-and-pricing/115/
The date will remain blank, as this could either count as the routine meetup for either July or August, for means of convenience.