About the MacGregor 26X

Wednesday, March 25, 2026

The Thimble List. Hayward, WI, snowmobiling

My son-in-law introduced me to the concept of the Thimble List, a collection of small, achievable experiences as an alternative to the large, high-effort, once-in-a-lifetime Bucket List, those must-dos before you die. One experience on my Thimble List was going snowmobiling—I’ve spent all but eight of my 61+ years in the Upper Midwest and this was something I’d never done but always wanted to try.

My good friend and sailing buddy John McSherry had invited me to go snowmobiling before, but the timing never worked out, until last weekend. It was late in the season, and the trails were no longer being maintained, but a foot of new snow was a good omen and a signal from the Universe that I needed to do it now. 

On Wednesday, Mick and I had lunch in Minneapolis while he finished up his on-call obligation for Delta Airlines, both of us hoping that his number wouldn’t come up (it didn’t). We drove the 140 miles to his cabin outside Hayward, WI, population 2,500. Homeland to the Ojibwe (part of the Anishanabe group), the town was founded in 1883 and named after Anthony Judson (A.J.) Hayward, a lumberman who opened the first sawmill here that became the center of the new community. Map link: Hayward, WI

Hayward today is a place that seems to punch above its weight. It is the county seat of Sawyer County, named after Philetus Sawyer, a prominent 19th-century Wisconsin politician and another (and aptly-named) lumberman. Al Capone, the Chicago gangster, owned a retreat here in the 1920s and 30s and was a regular visitor. Hayward is the home of the Fresh Water Fishing Hall of Fame and its iconic four-story, 143-foot muskellunge, the world’s largest fiberglass structure. The Musky Fest summer celebration is held every year the weekend after Father’s Day. This is trophy fish country—at least two world-record muskies have been caught in Hayward-area lakes, the largest weighing in at 69 pounds, 11 ounces. The Moccasin Bar, on the corner of Highway 63 and Dakota Avenue, has the world’s third-largest musky on display, along with a number of quirky stuffed animal dioramas, including chipmunks in hats, a weasel dressed as a cop and a boxing match between two raccoons, refereed by a groundhog. Another attraction is Scheer’s Lumberjack show, which also hosts the Lumberjack World Championships each July, where the best-of-the-best compete in sawing, chopping, speed-climbing, log-rolling and boom-running events. Hayward is the finish line for the American Birkebeiner ski marathon, North America’s largest cross-country ski race, which began in 1973 and now attracts more than 12,000 participants annually. I have completed two Kortelopet half-marathons as part of Birkie Weekend, and the thrill of skiing down Main Street as your name is announced and people cheer you on is an amazing experience. The Chequamegon Fat Tire Festival is held in September, where more than 3,000 mountain bikers compete on the Birkie trails. The nearby Namekagon River, a 101-mile tributary of the St. Croix, is a protected National Scenic Riverway, and offers world-class canoeing and camping. And Sawyer County boasts more than 600 miles of snowmobile trails, many connecting with trails in adjacent counties, making snowmobiling another huge draw. 

Mick and I arrived around 4:30 PM, assessed the snow conditions and the forecast, and decided to go out riding that evening. After dressing for the mild 40-degree weather and getting a ten-minute primer on how to ride a “sled,” we were off. We went down the driveway, around the corner to the boat launch, then took a lap around Little Round Lake for a warmup. Map link: Little Round Lake

It was pretty straightforward to control the sled, and accelerating, stopping and turning became second nature. The lake ice was solid, but bumpy, and going faster than 20-25 mph was a rougher ride than I was hoping for, and I rarely exceeded that speed range. Mick said that experienced riders will cruise on groomed trails at 40-60 mph, a speed that I was nowhere near ready for. After getting the hang of things, we crossed the road and entered Round Lake, crossing it south to north, a distance of about 3.5 miles. Our first stop was at Twin Lakes Tap, where we had a “safety meeting” to assess and critique my first ride. 



After our debrief and a chat with owner Dan, we followed Highway 77 another 2.5 miles northeast to Weber’s Northwoods Tavern. Newer owners Mike and Becki knew Mick, made me feel welcome and the walleye fingers and jumbo shrimp were terrific. Conversations at the bar centered around the seasonal outdoor calendar—snowmobiling and ice fishing were ending soon, then things would slow down until the fishing opener in May kicked off the angling and boating seasons. After dinner, we remounted and returned along the highway and across Round and Little Round Lakes, with good visibility from the SkiDoo’s headlight. I was able to speed up to 30-35 mph for brief stretches on Round Lake, trying not to let Mick get too far ahead. Before I knew it, we were back at the cabin and putting the sleds away. I’d done it—ridden a snowmobile—and had a good time and emerged unscathed. 

On Thursday, we slept in, played cards and made a quick trip into town. Mike, who owns the Grand Pines Resort next door, stopped by for cocktails, and told the story of a serious bar fight that occurred at the Twin Lakes Tap a couple of weeks ago, which had not come up the night before when we were there. Mick thawed some soup for dinner and made a salad, washed down with vodka tonics, then we watched a little TV before bed.  


Bonus Question: What is a Moylan Arrow? (answer at end of post)

Friday brought sunshine and temperatures in the 50s, creating standing water on parts of the lake, so we decided against any more snowmobiling and packed for home. On our way out of town, we passed Little Round Hank, a former Big Boy Restaurant statue that is now part of a local ice-out contest. Participants pay $5 to guess the day that Hank will fall through the ice, with the winner getting $500 and the rest going to charity. On our drive home, we passed a similar contest in Cumberland, WI, using a car. I later learned that both of these items will be retrieved from the lake bottom in the spring.  



Bonus Question Answer: A Moylan Arrow is the indicator on a dashboard fuel gauge that indicates which side of the vehicle the fuel fill is located. Invented by Ford designer Jim Moylan, this simple, practical solution to frustrating fueling experiences has been standard on most cars since 1989.





No comments:

Post a Comment