From October 23 through 25, the Village Cheese Shanty's last sandwich, the Chamber's two closing shopping events and a Halloween afternoon at the Old Art Building all land on the same short stretch of River and Main. By Sunday night the Cheese Shanty is closed for the season, and the rest of Fishtown's shops follow on their own schedules as October ends. For the next month, the village's public calendar runs mostly indoors and up the hill.
That's the useful way to read the next five weeks. Winter Leland is a smaller set of rooms, and it helps to know which rooms they are before the weekend is over.
The Weekend, Hour by Hour
The Leland Chamber of Commerce and the Village Cheese Shanty set their calendars separately, and the dates still fall on top of each other. Here's how they line up.
| Day | Where | What's happening |
|---|---|---|
| Thursday, Oct. 22 | Old Art Building | Iran, Middle East Instability & National Security, 6:30 to 8 p.m. |
| Friday, Oct. 23 | Fishtown | Last day for sandwiches at the Village Cheese Shanty |
| Friday, Oct. 23 | Downtown Leland | Broomsticks and Bubbles, 4 to 7 p.m. |
| Saturday, Oct. 24 | Fishtown | Cheese Shanty end-of-year sale |
| Saturday, Oct. 24 | Downtown Leland | Leland Fall Frenzy, 10 a.m. to 6 p.m. |
| Saturday, Oct. 24 | Old Art Building | Candy Leland Halloween at the OAB, 1 to 3 p.m., free |
| Sunday, Oct. 25 | Fishtown | Cheese Shanty closes for the season |
The Village Cheese Shanty at 199 W. River St. posts its season as April 18 through October 25, open every day from 9 a.m. to 5 p.m. until the end. Owner Jennifer Kareck gave The Leelanau Ticker the same sequence back in early September: sandwiches end Friday, October 23, and the shop's annual cheese sale runs the next day. On the shop's site, the last-sandwich date and the sale date sit on the same line, so the order is fixed. Sandwiches go Friday. The cheese goes Saturday.
Broomsticks and Bubbles fills Friday evening. The Ticker's fall guide calls it Leland's answer to Traverse City's ladies night, timed for Halloween rather than Christmas. Shoppers are invited to come in costume and "sip, shop, and sparkle" through town, with each shop serving "a special potion" and "magical deals." Saturday belongs to Leland Fall Frenzy, the Chamber's one-day sale at participating downtown stores. The Chamber hasn't published a store roster for either event, so the simplest plan is to walk Main Street and look for signs in the windows.
Families have a second Saturday stop. Candy Leland at the OAB runs from 1 to 3 p.m., it's free, and it overlaps the middle of Fall Frenzy. A loop through Fishtown for the cheese sale, a walk up Main for the sales and an afternoon hour at the OAB fits comfortably inside one day.
What Fishtown Looks Like on the Other Side
Fishtown Preservation describes the shanty businesses as generally open from early May through the end of October. A few open earlier or stay later, and each one sets its own hours. The organization also says Fishtown itself stays open to the public all year, winter included. So the docks, the weathered shanties and the river mouth stay open to walk into November, even as the shop doors close one at a time.
The dock was already quieter than usual this year. The National Park Service's South Manitou Island page, last updated September 25, 2026, says the Manitou Island Transit ferry isn't operating in 2026 because island construction leaves no safe place to dock on either island. In past seasons the ferry left from the Fishtown dock. For now, getting to the Manitous takes a private boat anchored offshore or a charter holding a Commercial Use Authorization, and NPS lists Manitou Fishing Charters as the current holder.
Main Street Loses a Lunch Counter in November
The Cheese Shanty's closing is seasonal, and it reopens in April. The bigger change on Main Street this fall is permanent.
Trish Kropp has run Trish's Dishes out of 407 S. Main St. since 2014. She told the Leelanau Enterprise in late August that she plans to close the storefront in November and run the business as a wholesale operation only. The sandwiches will keep going out to the 15 locations in Leelanau and Grand Traverse counties that already carry them. "I will miss feeding people because I really do enjoy it," Kropp told the Enterprise.
The address has a longer history. Kropp moved into the Main Street building after Stone House Bread left in 2013. Before that, Trish's Dishes started in Northport in 2008 and spent about three years in Lake Leelanau. She told the Enterprise she hopes to find a property somewhere in Leelanau County to work out of and to grow the wholesale side. The Enterprise didn't report a final day for the storefront. The paper said only that it would close in November, so the next few weeks are the window for a sandwich across the counter on Main.
Taken together, Leland goes into this winter with both its Fishtown sandwich counter and its Main Street sandwich counter closed for walk-in lunch. One reopens next spring. The other moves to grocery coolers around two counties.
The Old Art Building Holds the Calendar
As the Fishtown shops close for the year, the Old Art Building carries most of the village's evenings. Its fall schedule has an event almost every week from the closing weekend into December:
- Thursday, Oct. 22. Iran, Middle East Instability & National Security, a livestream with Northwestern Michigan College's International Affairs Forum. Wine reception at 6:30 p.m., presentation and Q&A at 7.
- Saturday, Oct. 24. Candy Leland Halloween at the OAB, 1 to 3 p.m., free.
- Friday, Oct. 30. Little Dipper with special guest Elisabeth Pixley-Fink, 7 to 9:30 p.m., doors at 6:30.
- Sunday, Nov. 1. Lamb's Leland Songwriters Concert 2026, 6 to 8 p.m., doors at 5:30.
- Thursday, Nov. 12. "Boiling Point: How America Brought War To Ukraine," the next free International Affairs Forum session, with the same 6:30 p.m. reception and 7 p.m. start.
- Saturday, Nov. 14. Joan Shelley and Nathan Salsburg, 7 to 9:30 p.m., doors at 6:30.
- Thursday, Dec. 3. Hand-Painted Holiday Candles, an À La Table workshop, 6 to 8 p.m.
The forum nights also come with dinner. According to the Ticker's fall guide, the OAB has partnered with Peninsula Provisions in Lake Leelanau this fall to offer $10 soup and bread before the International Affairs Forum events. On a Thursday in November, with fewer kitchens open in the village, that's a full evening out in one building.
Where Dinner Happens After the 25th
Leland Lodge calls itself the area's only year-round hotel, restaurant and bar. Its restaurant, Bogey's 19th Hole, lists dinner Tuesday through Saturday from 5 to 8 p.m., with the bar opening at 4. The Lodge's other room, The Wine Cellar, has already closed for the season and expects to reopen in June 2027. So Bogey's is the Lodge's winter dining room, and it's closed Sundays and Mondays.
The Bluebird's own site says hours are irregular because of staffing and asks guests to call ahead. That's sound practice for any Leland kitchen between now and spring. Off-season hours change week to week, and a phone call beats a cold walk to a dark door.
When Main Street Fills Back Up
The quiet stretch runs about a month. The Leland Chamber's holiday calendar starts the night before Thanksgiving and keeps going into mid-December:
- Light Up Leland: Wednesday, Nov. 25, 5:30 to 7:30 p.m.
- Black Friday in Leland: Friday, Nov. 27, 10 a.m. to 6 p.m.
- Small Business Saturday: Saturday, Nov. 28
- Cocoa Crawl: Saturday, Dec. 5
- Leland Sip and Shop: Thursday, Dec. 17
That puts Leland's year in a clear order. The closing weekend of October 23 through 25 ends the Cheese Shanty's season, and Fishtown's other shops wrap up around the end of October. Trish's Dishes leaves its Main Street storefront sometime in November. The Old Art Building and Bogey's carry the village through the first weeks of November. Then Light Up Leland on November 25 brings the shops back out for a holiday season that runs five events deep, through December 17.
If your Leland cottage is about to sit empty for the first time, or you're working out who watches the house once the Cheese Shanty's sign comes down, Peter Fisher offers property management for Leelanau County owners who head south for the winter. Schedule a Leelanau County consultation, and Peter can walk you through what off-season care looks like for a property in the village.
