Leland's
Sleeps 6 · Hot tub · Walk to beach · 25 min to the wine trail
The largest of the three — hot tub on the deck for the crisp-night end of a tasting day.
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Locals will tell you the secret about wine country up here: the best month on the trail isn’t July. It’s September into October, when the crush is actually happening, the hillsides go crimson and gold, the tasting rooms exhale, and the drive itself — M-22 wrapping the peninsula, orchards on one side, water on the other — becomes the main event.
Fall is when the Leelanau Peninsula Wine Trail runs its three best programs of the year, and two of the three are built for weekdays — which means quiet tasting rooms, winemakers with time to talk, and cottage rates that beat peak summer. Here’s how the season lays out, and how to build a trip around it.
Three ways to drink in the harvest
Harvest Days — all September. The trail’s month-long harvest celebration. The Harvest Club pass (~$75) makes you a “member for a month” at every trail winery: a complimentary flight or tasting at each stop plus 15% off bottles — valid every day except Saturdays. Read that again: the trail is literally engineered for a Sunday-to-Friday trip. Come Tuesday, the tasting rooms are yours.
The Hunt for the Reds of October — weekdays, all October, starting Thursday, Oct 1. The counterpoint to summer’s whites and rosés: every participating winery pours a red the winemaker hand-picked, plus “cork cash” to spend along the trail. Weekdays only, all month — so it pairs with peak fall color, empty roads, and the cheapest great nights of the season. Cab Franc tastes better when the vineyard behind it is on fire with color.
Toast the Season — November 6–8 and 13–15. The trail’s holiday kickoff: two ticketed weekends of special pours and pairings as the tasting rooms turn festive — and the trail’s own calendar says its events sell out quickly. After the color drops and before the snow settles in, this is the reason to point north in November that almost nobody knows about.
(Old Mission fans: the other peninsula runs its own fall events — see our Old Mission Winery Events post and wineriesofomp.com.)
Practical details
Where: Leelanau Peninsula Wine Trail — ~25 wineries looped by M-22 and M-204, roughly 20–45 minutes from our Traverse City cottages.
When: LP Harvest Club: September 1–30 · Hunt for the Reds: weekdays, October 1–31 · Toast the Season: November 6–8 & 13–15.
Tickets: Harvest Club, Reds of October, and Toast the Season passes at lpwines.com / MyNorth Tickets. The trail’s events sell out — buy when they open.
Getting around: Designate a driver, book a shuttle (Lakeshore Shuttle and others run trail routes), or keep it to 3–4 wineries with lunch in Suttons Bay. Fall light ends early — start by noon.
Eat: Farm Club and Hop Lot on the trail’s south end; Martha’s Leelanau Table or Wren in Suttons Bay; Fischer’s Happy Hour Tavern up M-22 if you know, you know.
Official source: lpwines.com
Three things locals do that visitors miss
- Go midweek — the whole season is built for it. Harvest Club skips Saturdays, Reds of October is weekdays-only. A Tuesday–Thursday in late September gets you member treatment at 20+ wineries, peak-color drives, and no lines anywhere.
- Watch the crush pad, not just the tasting room. In late September the fruit is actually coming in — ask at the bar and most wineries will happily point you to where the sorting and pressing is happening. It smells like the whole season.
- Take the long way home through Leland. End tasting days at Fishtown around golden hour: Village Cheese Shanty sandwich, walk the docks, then the M-22 drive back as the light goes long. That hour is the postcard.
FEATURED IN OUR GUIDEBOOK
Where to stay for a fall wine trip
Our three Traverse City cottages sit side by side less than a block from the State Park beach — about 25 minutes from the first tasting rooms on the trail, with downtown TC’s restaurants on the way home. Fall midweeks are the sweet spot: summer rates are behind us, the hot tubs are not.
Esch's
Sleeps 4 · Hot tub · Walk to beach · 25 min to the wine trail
Two bedrooms, built for a couples' wine trip. Fireplace on, glasses out.
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Oneida's
Sleeps 4 · Hot tub · Creekside setting · 25 min to the wine trail
Wooded and creekside — fireplace inside, the one that feels most like fall.
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Partial Estate Retreat
Sleeps 8 · Two cottages on one property · 25 min to the wine trail
Doing the trail with two or three couples? Esch's and Oneida's book together as a single stay — everyone gets their own cottage, one shared fire pit at the end of the night.
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Entire Estate Retreat
Sleeps 14 · Three cottages on one property · 25 min to the wine trail
All three cottages on one property — the whole group's harvest weekend with separate kitchens and one shared fire pit.
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Prefer the coast? The Bou, our Lake Michigan cottage in Frankfort, sits about an hour south of the trail — close enough for a full tasting day, far enough that you end it with the lake out the window instead of the crowd. October is its last full month before the season winds down. See The Bou →
Booking direct: OTA fees add 15–18% to your total. Book with us directly and skip them — same cottage, better rate. September midweeks are open now; the trail’s ticketed weekends will not stay that way.
Stay north.
— North Coast Cottages, curated cottages on Michigan’s Lake Michigan coast
THE SCENE
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Events, openings, and the kind of weekend you make a trip around — plus first word on open cottage dates.