An owner up there is on this site i think..cant think of his name
You are thinking about Gary Dalzell @ Woodside Cottages. Not 100% sure if you can ride right from his place.
To the OP.....why do you want to stay in Bayfield anyway? Nothing much to see in winter anyway....IMO
It is a trip that I am planning with the wife. She wanted to go somewhere different this year. She's heard about the restaurants and B&B's up there. Doesn't sound like much of it is open though.
We've stayed in Cable before (Telemark Resort).
Another option was Sault Ste. Marie..............
You could stay somewhere around Washburn. Washburn is right on the trail to Bayfield if they decide to groom that part of the trail. We always go on a day trip to Bayfield while staying on Lake Namakegan. That is when the trail is open. Some years they don't groom to Bayfield for various reasons. However there is endless riding up in that area north of hwy 2. There is usually a little more snow up there also. There are not a lot of landmarks. You have the Pub and Grub - which is always great - and you have Port Wing and I think Herbster. But there is very little traffic and a lot of miles of really nice trails. Bayfield itself has never been a real snowmobile friendly place. Not in the 20 years we have been going there anyway. But there is stuff to see there. Mackinack island is like going back in time to the 60s. I have never seen so many VW bugs in one place. I doubt many of them run but they don't throw them away. One year when the big lake was frozen we ran from Mackinac back to Washburn. There was a set of tracks we followed. We got to Washburn and pulled in to gas up and the guy at the gas station said that it had just frozen up a week ago and there are currents out there and the ice is never safe. So I guess i don't recommend that particular route. Other than that it is a great area to ride. Not many trail stops but a lot of scenery.
i'd say he meant madeline island