Along the Peninsulas This Coming Week

Cooler evenings, vineyard roads, and a week of local gatherings from Glen Arbor to Old Mission.

The light is changing now. By early evening, porch lamps are already showing up in the villages, and the wind coming off the lake has enough edge in it that you notice collars turned up and hands wrapped around paper cups. Along M-22 and Center Road, leaves are starting to gather at fence lines, a chalkboard sign leans a little in the breeze, and somebody pauses under a window to smooth a folded program before heading inside.

Over the next week, the calendar stretches across the peninsulas in that steady October way. In Glen Arbor, River Club Glen Arbor has Prima on Friday, October 2, and Luke Duo on Saturday, October 3. In Suttons Bay, the Leelanau Wine Trail Tour continues daily through the week out of Grand Traverse Bike Tours, with the route threading through vineyard country while the season still holds. Out on West Bay, Sunset on the Bay continues from Thursday, October 1, through Tuesday, October 6, and Wine Down Wednesday returns on Wednesday, October 7 aboard Discovery Cruises.

There are also a few longer-running stops worth keeping in mind if you are moving slowly through the county this week. In Leland, the Leelanau Historical Society Museum continues its A-Z of Leelanau History – America 250 Exhibit during regular museum hours, a good fit for this time of year when more people start lingering indoors a little longer. And if you are looking just beyond this immediate week, the next run of Sunset on the Bay resumes later in the following week, from Friday, October 9, into the weekend.

Looking a few days farther out into the second half of the coming week, the shape of things gets fuller. Bay Theatre in Suttons Bay has May Erlewine and Ani Mari on Saturday, October 10, as part of its Live at the Bay fall series. French Valley Vineyard hosts the Vineyard at Sunset 5K on Sunday, October 11. Then on Monday, October 12, Leland marks Indigenous Peoples’ Day through the Leland Cultural Campus, with the gathering centered at the Old Art Building and Leelanau Historical Society Museum. That same stretch of days also brings more evening sailings on West Bay, with Sunset on the Bay running October 9, 10, 11, and 13, and another Wine Down Wednesday on October 14.

So that is the week ahead around Leelanau, Old Mission, and the Lake Michigan shore towns: a few music nights, a museum afternoon, time on the bay before the cold really settles in, and one of those October schedules that seems to travel by conversation as much as by poster. You hear about one thing at the post office, another at the bakery counter, and by dusk the roads are already darker between towns.

Event Info:
River Club Glen Arbor events 2026
Leelanau Wine Trail Tour
Sunset on the Bay
Wine Down Wednesday
A-Z of Leelanau History – America 250 Exhibit
The Fall 40: Your Guide to Autumn 2026 in Leelanau County
Indigenous Peoples’ Day