In November, the light leaves early, we experience three seasons before lunch, and the crows and blue jays are happy to be lords of the land again.
But we’ll tell you what: we’ve come to love it.
Yes, the ferry ride can get bumpy in a gale, but the captain runs a tight ship, and the island is worth the crossing. Why? Because there are more ways to connect with the community on Drummond Island in late fall and winter than throughout the whole summer!
Holly Daze — Saturday, November 14, 2026
Fourteen businesses and organizations are taking part in this year’s Holly Daze, from restaurants and gift shops to the hardware store and local studios.
The event is a chance to support the businesses, artists, and makers who contribute to island life throughout the year. And it’s super fun!
Past Holly Daze celebrations have included scavenger hunts, raffles, prize baskets, handmade crafts, local artwork, holiday treats, and some pretty creative contests. Northern Properties even got in on the action with a giant gumball machine and a chance to win one of your own.
You never quite know what you’ll find. One stop might have handmade pet bandanas, another might have original artwork, baked goods, or a raffle prize worth taking a chance on. And if this year’s festivities are anything like years past, there’ll be plenty of reasons to shop local.
Grab a coffee, make a loop, and cross off a good chunk of your Christmas list without leaving the island. Holly Daze runs from 10 a.m. to 4 p.m., so you’ll have six hours to see what the island businesses have in store. Pun intended.
Ladies Night at The Northwood
Keep an eye out for Ladies Night at The Northwood starting in November. Past events have featured shared platters of appetizers, specialty drinks made just for the occasion, local vendors, door prizes, raffles, and Christmas BINGO.
Come with friends, or come alone and leave with a few new ones. Follow The Northwood on Facebook for dates and vendor announcements.
Pins Bar & Grill
Pins Bar & Grill is keeping things going this fall and winter, with pizza, cold drinks, and new food specials. The bar is open Thursday through Saturday from 3 to 11 PM, with the kitchen serving from 4 to 9 PM. Golf members can also take advantage of their Pins discount through December 31.
Pins Bar & Grill was closed last winter and we missed them dearly! Welcome back!
A New Way to Connect
There’s also a new Facebook group, Drummond Island Community & Connection, built on a refreshingly simple idea: be decent to each other, share what you know, support local businesses, and maybe meet someone outside your usual circle. Residents, seasonal residents, visitors, artists, businesses, and community organizations are all welcome.
The group’s founder, Ashley, also owns Fall But Once, an artist studio where she offers art classes. Classes are planned for December through February, with a break in March. Pre-registration is required at fallbutonce.com/events.
Come Over. Stay a While.
If you’ve been looking for an excuse to visit Drummond Island, but long summer ferry lines and crowded restaurants aren’t your thing, November might be your month!
We even have repeat guests who make spending Thanksgiving with their families on the island an annual tradition.
Northern Properties has vacation homes that stay open all year to accommodate your fall and early winter wanders.
So round up your favorite people, pick a weekend, and come see what we’re up to! Make a weekend of Holly Daze, get a head start on Christmas shopping, or gather the family for Thanksgiving somewhere a little different.
Browse our available vacation homes and book yourself a little island time.
Tip: Wear layers.