Locally, one of the main events on my radar in January is First Sunday which falls on January 3rd. It's a gameday at the Lake Geneva Games store. They are located at 918 S Wells St, Lake Geneva, WI 53147 and their phone number is (262) 885-1515. The event runs from Noon until 9 pm and is mostly about pickup boardgames though planning particular games privately or on Facebook is certainly encouraged. Sign up for this event and discuss it further on Facebook here.
There will also be a Burlington Gameday scheduled for January on the third Saturday, the 16th, with details at the Burlington UCC Game Day group on Facebook here. It will be held in Burlington, WI at the Plymouth UCC space, taking place from approximately 11 am to 5 pm. All are welcome! The third Sunday this month feature A Gathering of Gamers on Sunday, January 17th, set up by the South Lakes Area Gamers here. The event takes place at the Pizza Ranch in Elkhorn, WI, and requires a $12 fee for the all you can eat pizza and fried chicken buffet (salad bar, soft-serve ice cream machine, etc.) plus unlimited soft drinks and coffee from 11 am to 8 pm.
There still time to make plans for Winter War 43, to be held January 29-31, 2016, at the Hawthorn Suites in Champaign, IL. Winter War is one of the longest running game conventions in the country. The flyer for Winter War can be downloaded from here. To get an idea of the scope and type of events that will take place, you can check out last year's program here. Current event listings are here.
Farther from my locale . . .You can also find a whole list of gaming events all around the country and beyond on Warhorn.net here. Some of the events include (highlight and right click/search for more information on any of the below):
Jan 2, 2016 Dimgaard Online Game Day Online
Jan 2-3, 2016 FarWest MiniCon San Jose, CA
Jan 8-9, 2016 ShadowCon XX - FORGE Schedule West Memphis, AR
Jan 8-10, 2016 IllogiCon V Cary, NC
Jan 8-10, 2016 OrcaCon 2016 Everett, WA
Jan 9, 2016 BAPS Game Day Santa Clara, CA
Jan 14-17, 2016 Midwinter Gaming Convention 2016 Milwaukee, WI
Jan 15-17, 2016 King (Cobra) Con Bloomington, IN
Jan 15-17, 2016 Magic City Comic Con 2016 Miami, FL
Jan 15-17, 2016 Marscon - Project Crusaders Williamsburg, VA
Jan 15-17, 2016 Marscon - Savage Worlds Williamsburg, VA
Jan 15-17, 2016 MarsCon 2016 Williamsburg, VA
Jan 15-17, 2016 MarsCon 2016 - Dark Passages Williamsburg, VA
Jan 15-17, 2016 Ohayocon 2016 Shadowrun Events Columbus, OH
Jan 15-18, 2016 SCARAB Gaming Convention Columbia, SC
Jan 16, 2016 OSCon 5.5 Toronto, ON, CA
Jan 16-17, 2016 SnowCon 2016 Bangor, ME
Jan 16-17, 2016 Star Trek: Command Decision Bangor, ME
Jan 20, 2016 Wasatch Front Pathfinder Society Wasatch Front, UT
Jan 22-24, 2016 VerminCon 2016 Vermillion, SD
Jan 23-25, 2016 PFS@Cancon16 Canberra, ACT, AU
Jan 27-31, 2016 Conception 2016 Christchurch, DOR, GB
Jan 29-31, 2016 GHD Game Retreat Hudson, OH
Jan 29-31, 2016 Secret Mission Con Atlanta, GA
Jan 31, 2016 MEGAGAME: Watch the Rising Sun Sarasota, FL
Some of this information (and more can be had) is from the excellent lists on upcomingcons.com/gaming-conventions, GameConventionCentral.com, HMGS (the Historical Miniatures Gaming Society), and as well as many, many gamers on Facebook and Google Plus, to whom I am grateful for the help in this compilation. Thanks so much and have a great game!