I'd start small....250 people is huge....and that's just one from each house!
I would start with your immediate neighbors...either those on your street or, depending on how small your lots are, those who back up to you....at any rate start with about 10 to 15 households...either include kids or not.

As you said, chili works well...as does various things on a grill....burgers, hot dogs, brats, chicken breast strips, skewered shrimp etc.
A big container of turkey or pork cooked in BBQ sauce is good. And you can do a long slow cooked brisket as well.
I also think that once a month might be a bit often...but perhaps not in the summer.
Linda C

Once a month is a bit ambitious - and from my experience in different neighborhoods, both old established and new developments, it tends to work once then dies a natural death... particularly if one person is attempting to spearhead the project and do all the work. Sadly, lots of people have their own isolated and insulated lives and though they may be social choose not to socialize - perception being that being social in a neighborhood creates demands they're not willing to commit to.

I think the basic idea is nice, especially if the neighborhood is new and it's an opportunity for people to introduce themselves, but maybe a once a year block party would make more sense; outdoor grilling with a more picnic-like aspect which could include children would be less intimidating. Or an ice cream social, again outdoors.

Thanks! What total nut case would consider this whole stupid idea? That would be me.

This neighborhood is socially connected because it has generations that grew up together on the lake and all have remained here, we are new and perhaps it is not a good idea.

I am going to skulk off now and hide under the bed..or not.
Maybe drink..or mainline heroin..or spend the next 100 hours at a Crisis Nursery. I like the last one. That will cure me any dumb idea for the next five years for sure. I am not stable enough to handle severely disturbed children in groups.

Do you have a park or common green area in the neighborhood? If so, you might consider doing an outside pot luck party, where you grill hot dogs & such, and everyone else brings sides, desserts, drinks, paper goods etc. You could do it on a weekend afternoon. Then kids can play while adults chat.

I agree that once a month is too ambitious, especially if you're the one hosting every time. I'd shoot for twice a year, unless you can encourage others to host. An outdoor event is, of course, governed by weather, so that would also limit the frequency. But I think it's nice idea to get the people in the neighborhood to socialize.

Well -- you could try for a Classic Community Cookout during a long weekend ...... send out Save-the-Date notices ...... and then E-vites and drop invitations into mail boxes. There could be a theme "Italian Vacation" or "Texas Camp Cookout" Theme parties tend to work because you could do a kids costume (best cowboy Or best toga) contest, or spagetti-eating (or hot dog or ice cream) contest etc. Find out about stuff like rental costs for those long tables, chairs etc. Can you block off a street? Ask your local Neighbourhood Association and the local police too.

BUT always best to start small -- and build up to the Community Cookout. See how folks feel about such an event .....

Just some thoughts .....

At the end of our block, they hold an annual pot luck for the neighborhood. Its a cul de sac street, so they close it off to traffic, put out tables, everyone brings a pot luck dish. The Email invitation says that people with the last initials A-G bring salads, G through o bring main dishes, a small group brings paper plates and silverware Everyone brings their own beverage.
It has grown over the years. Its wise to start with people who live in a connected area first and work from there, and have it outside. You can get permits to close off a street and have a block party. Just be sure to invite everyone on that block to begin with.
Where I lived before we had walk streets with no traffic so it was easy to put tables out and do a block party on holiday weekends. July 4, etc., Dont forget you do need a clean up crew for the next day.
If you are willing to organize this--its wonderful. People are happy to go to these block parties, it just takes somebody who is interested in setting it up. Discuss this with several neighbors and together pick a day and a place to have it--outside. Send out flyers. Yippee block party. Get Email addresses for next year. Guests sign in at party.
Take photos--put one on next years Email announcement & flyer, and presto--you have the 2nd annual block party. Then when you run for mayor--you have a mailing list and supporters.