May Light, Muddy Boots, and a Full Stretch of Plans
A calm look at what’s coming up across Leelanau, Old Mission, and the Lake Michigan shore—May 15–May 29, 2026.
This is that middle-May stretch on the Coast where the air still has a cool edge to it, even when the sun shows up. Screen doors start to swing again, but you can hear them hesitate—one soft creak, then the click. Along the sidewalks you’ll see puddles holding last night’s sky, a scatter of tulip petals pinned to wet concrete, and grit still tucked into the seams where winter lived. Somebody stands a second longer at a community bulletin board, finger tracing a flyer corner before smoothing it back down.
Right now through Sunday, May 17, the Leelanau Peninsula Wine Trail has a May 15–17 weekend running across participating wineries, and you’ll hear it the way locals hear most things—mentioned at the counter while coffee is poured, or in passing when someone’s shrugging into a jacket. On Friday afternoon, Boathouse Vineyards in Lake Leelanau has a Vineyard Walk on the books. Also Friday, Bel Lago in Lake Leelanau has live music on the calendar. Saturday night, May 16, there’s a Jon Muq show at the Old Art Building in Leland—one of those evenings where the parking lot gravel talks under your tires before the door closes and the room goes quiet.
Sunday, May 17 brings a quieter, hands-on note up in Northport: Two Fish Gallery is hosting “Opening Doors,” a beginner-friendly watercolor workshop. If you’ve been around town long enough, you know the look—paper taped down, a cup of rinse water turning cloudy, and that first pale wash drying unevenly near the edges while people lean in to see what the brush is doing.
As we move toward Memorial Weekend, Saturday, May 23 is a busy one that’ll show up in traffic patterns and conversation. The Bayshore Marathon (and the half marathon, 10K, and kids run) is set for that Saturday, running the Old Mission Peninsula routes and pulling a lot of early-morning headlights out toward the bay. Over in Leland the same day, the 14th Annual Leland Air takes artists out across Leelanau County to paint and draw, then brings the work back for the evening: Leland Air Opening Reception & Exhibit at the Old Art Building. The exhibit stays open daily May 24 through May 28, which makes for an easy stop in that in-between time of day when you’ve still got daylight, but you’re ready to be indoors for a bit.
And for a longer thread you can catch anytime this week, Glen Arbor Arts Center’s main gallery show runs through May 28—one of those dependable reasons to step off a damp sidewalk and into warmer light, where you can hear your own footsteps change on the floor. Looking a little farther out inside our two-week window, Saturday, May 30 brings Hairball to the Leelanau Sands Showroom in Peshawbestown—louder, later, the kind of night that contrasts with the soft spring evenings we’ve been living in.
Event Info:
Old Art Building Calendar
Bayshore Marathon
Leelanau Peninsula Wine Trail Upcoming Events
Glen Arbor Arts Center All Events
Boathouse Vineyards Events
Bel Lago Winery & Cidery Events
Two Fish Gallery: Opening Doors Watercolor Workshop
Leelanau Sands Casino Events