Harbor Springs, Michigan: Population 1,274, Zero Chill About Their Cookies

If you've ever wanted to visit a place where the yachts outnumber the year-round residents' knees (the original ones, anyway), welcome to Harbor Springs, Michigan. This resort town on Little Traverse Bay was recently run through the roast machine at RoastMyTown.com, and honestly? It took it like a champ. Probably because it was too busy sipping something chilled on a veranda to notice.

Let's dig in, with love, and with facts.

Harbor Point: Gated, Presbyterian, and Proud of It

Start with the roast's favorite target. Harbor Point is a gated summer enclave founded in 1878 by Presbyterians from Lansing, and the cottages tend to get passed down through families like a very expensive casserole dish. No automobiles are allowed inside the grounds of Harbor Point, according to one local history page. So the rich have solved traffic by simply banning cars. Honestly, iconic.

But here's the thing: the roast is a little unfair, because the whole region was built for this. Harbor Springs began to be known as a summer destination in the 1870s, and it became a resort where socialites could escape the pollen, dust, and heat of the city. Boarding houses and hotels were built for the summer guests, and the associations of Wequetonsing and Harbor Point were formed as resort communities. In other words, Midwesterners have been fleeing Chicago humidity here for roughly 150 years. The grain-futures jokes write themselves, but so does the real estate listing.

Speaking of which, the money hasn't gone anywhere. The local tax assessor reported that of 1,370 parcels of real property, only 449 have a principal residence exemption, meaning they're claimed by year-round residents. Do the math: roughly two-thirds of the town's property belongs to people who are, at this very moment, somewhere else.

God's Waiting Room (With a Really Nice Marina)

The roast says Harbor Springs is too small to call itself a city. The census agrees on the "small" part: 1,567 people in 2000, 1,194 in 2010, and 1,274 in 2020. That's a town that has basically been holding its breath for two decades.

But let's give credit where it's due. This tiny place has real history. Chief Andrew Blackbird was appointed postmaster in 1858. The original Emmet County Courthouse, built in 1871, later became City Hall and today is the home of the Harbor Springs History Museum. The museum covers everything from the area's first residents, the Odawa to inventor Ephraim Shay, who made his mark here with his geared locomotive. That's a lot of résumé for a town the size of a Costco parking lot.

And the "nothing happens here" claim? Please. The Fourth of July celebration has been drawing families back for over a century with its small-town parade and fireworks. Meanwhile, the biggest recent local news involved a conservancy protecting forested acres from developers. The town's villain origin story is "we saved some trees." Terrifying.

The Tunnel of Trees: Yes, It's Just Trees. Yes, You'll Cry Anyway.

The roast calls M-119 "literally just trees over a road." Technically correct, which is the best kind of correct, and also the kind that gets you uninvited from fall color tours.

The Tunnel of Trees runs north from Harbor Springs toward Cross Village, hugging the Lake Michigan bluff. Along the way, you can stop at the Good Hart General Store, established in 1904, for a famous pot pie before continuing to Cross Village and the 1920s craftsmanship found at the historic Legs Inn. So yes, the drive is "just trees," but the trees come with pot pie and a folk-art Polish restaurant covered in driftwood. Narnia never offered that.

Want to get out of the car? The Offield Family Viewlands, a former golf course, now features miles of trails and panoramic views. And if you're a winter person, there's downhill skiing at Nub's Nob and Boyne Highlands. Yes, two ski resorts! Your Chicago relatives will arrive in October, say "hmm, nice trees," and then take 400 photos.

Whitefish on a Kaiser Roll: A Defense of Big Cookies

Now, the food roast. Authentic Polish cuisine and massive cookies are "peak cuisine"? Reader, we are not offended, because we've been to Michigan and we know that's a flex. Legs Inn's Polish menu is a regional institution, and Tom's Mom's Cookies, which has even been featured on "Under the Radar Michigan," is the kind of bakery that makes you question every diet decision you've ever made.

But the dining scene has legitimately grown up. Stafford's Pier Restaurant provides upscale dining and breathtaking views of the harbor, while Paper Station Bistro is well known for its sandwiches. And the former Birchwood Inn has been reborn as OTIS, a boutique hotel with 31 rooms of "mid-century respite." There's even Pond Hill Farm, with hayrides and pumpkin patches in the fall and wine tastings and craft beers year-round. Whitefish on a kaiser roll may not be fine dining, but we'd eat it on a dock at sunset every single day.

Coming up on the calendar, the Harbor Harvest Fall Festival is a fall tradition. Expect cider, pumpkins, and a whisper of "oh my, is that a teenager?"

The Verdict

Harbor Springs is old money, older demographics, and absurdly good scenery, and it knows it. It's small, it's gated in places, and it's the kind of town where the cookies are larger than the crime rate. Is it overrated? Only if you consider deep natural harbors, Victorian cottages, ski hills, and a pot pie in the woods overrated. (We don't.)

Think we were too nice? See the full roast on RoastMyTown.com.