Here in Oregon there's a very healthy collaborative atmosphere in the wine industry, which means there's lots of ways to connect with other winemakers. During harvest I try to stop by other people's wineries and invite people over to mine to discuss the vintage, smell and taste ferments, and see friends that have disappeared into the grapes like myself. There are a few Oregon winemaking Facebook groups that have proved very valuable as well - sourcing grapes, barrels, and seeing trends across the state as they happen. Also very helpful in finding last minute troubleshooting forklift repair to fruit hauling.
I participate in a couple of online groups, however, my main means of connecting with peers is visiting with them, or grabbing a beer and talking shop. I've gained far more insight with more casual in person discussions then more formal or online methods.
My favorite way to connect with other winemakers is during more casual gatherings that are more centered around like a potluck or family oriented event. I find when meetings or gatherings are more laid back it allows everyone to connect and share more authentically vs. a business meeting or networking event. While the day to day operations don't allow for a lot of excess time I do participate in several organizations such as Maryland Winery Association and African American Association of Vintners as well as less formal meet ups with other wine makers which always prove to be valuable to know you're not alone in this journey.