Just throwing some ideas out there/ I've put together a few GTG's and have learned some lessons.
In past experience meeting at an AD isn't always the most fun option. Odds are that the AD is not going to have anything we haven't seen before. Don't expect a Daytona C or BLNR to make its way out...
Meeting over some drinks and talking watches is usually the best setting.
Somewhere that has a decent level of privacy for security purposes is usually best.
I personally like to bring a few watches. I bring a watch roll and leave it open on the table (obviously in sight) and encourage others to do the same.
Going to a crowded restaurant and passing watches around the table and taking pictures etc tends to draw the wrong kind of attention.
Obviously it goes without saying that everyone pays their own way. If you order a drink pay for your drink.
Mohegan isn't a bad option. Sunday's during the day are usually crowded though with people making day trips to the casino. If there is somewhere there that we could sit at some tables or high tops without necessarily having dinner and just order drinks?
Here's another option. Just something fun for a Sunday. It's earlier in the day so it won't take up your entire Sunday:
Caffeine & Carburetors Sunday October 16 @ Waveny Park in New Canaan CT
http://caffeineandcarburetors.com/
Pretty awesome time. Hundreds of crazy cars. Lots of watch spotting. Could go to breakfast or lunch afterwards.
Cigar spot in New Haven:
The Owl Shop
268 College St New Haven CT
Also worth mentioning is that it seems College St in New Haven.
I'm thinking time wise Middle September and on is best. Get past the summer and Labor Day etc.
Let's get this going! Feedback and suggestions are welcome and needed to get this to happen.