Now is the most wonderful time of the year for a family-friendly Harbor Springs winter vacation. Shake up some new Up North holiday traditions.

Let me start by saying I’m a mom of two toddler-aged boys. I don’t go out with them and enjoy Northern Michigan’s bountiful outdoors as much as I should. Especially in the wintertime. Because it’s hard.

If you’ve had young kids, you’ve been there. Bundling layer on layer to noncompliant littles isn’t an easy task. Add the cold temperatures and an inevitable toddler tantrum (or two!)—because, no, you can’t eat snow—the lengthy efforts are for a short amount of playtime. You get it.

But when asked to head north to write this travel piece about a weekend Harbor Springs winter vacation, I only needed a little push … and I was all in.

Featured in the December 2019 issue of Traverse, Northern Michigan’s Magazine. Get your copy.

Snowpants? Packed. Road snacks? Yep. Sunglasses? Absolutely. Our family of four is ready to go.

Snowmobile tracks line the road as we drive closer to Emmet County. My husband and I are slightly giddy as we drive our two sons to our holiday trip to Harbor Springs and points beyond. At three and almost two years old, we know better than to tell them any details in advance about our adventure—we’d never hear the end of it. So we keep our upcoming destination a secret between us. And instead, when we are asked where we’re going, we simply tell them, “North.”

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We hear our boys’ first gasps of excitement from the back seat once we arrive in downtown Harbor Springs, as they spot the biggest Christmas tree they have ever seen, right in the middle of the street. The bustling heart of Harbor is beautiful—but we don’t stop driving yet. We roll down the window to wave at the marvelous tree and holler, “See you soon!” as we drive higher in elevation. Our first stop is for a snack break.

We unpack our treats and soak up the view from atop the city’s boardwalk at the end of Spring Street. I could have stayed up there staring at the view for hours. (See the view in the video below!)

But we are on a mission to explore. On our journey back down the hill to downtown, we share the streets with people traveling on foot from Bluff Drive to the post office—arms filled with presents for loved ones. The scene is straight out of a storybook.

Artist Trisha Witty is setting up an outdoor art gallery in her courtyard just a couple of doors down from the post office. A rare treat when the weather is just right in the winter. I make a quick stop and see some of her latest oil works while the boys take in some fresh crisp air out front. As always, her paintings capture Harbor’s charm in a way only Trisha can. I’m in awe.

As we continue wandering downtown, almost every storefront on Main Street has gorgeous garland draped from their front doors and windows—competing for the Chamber of Commerce’s window decorating contest. Local pride at its finest.

But walks in a double stroller for lake-loving boys are short-lived. And today our boys only have the patience to walk to a handful of stores before wanting to see the lake again. Once we get there, they ask where the boats are. So we go on a treasure hunt to find them. X marks the spot! It’s new for us all to see so many dock sections stacked up on land for their winter hibernation.

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My mind drifts to memories of the harbor in its summer glory for a brief moment before getting ripped back to life with toddlers. “Mommy, Daddy! I’m hungry!”

Being in the holiday spirit, the candy-cane colored awning of Pierson’s Grille & Spirits caught our eye. Mac ’n’ cheese for them. Avocado tacos and a burger for us. We feel like we’re lounging in a local ski resort thanks to the authentic antique signs, skis and snowshoes on the walls. The black and white framed photos are of the owner’s mother. Arcade games and a lesson in shuffleboard for the boys is our after-meal treat.

With full bellies and the afternoon upon us, Tunnel of Trees, here we come!

Our youngest doesn’t make it far into our drive up M-119 before closing his eyes. And our tyke can’t stop staring to the left, squealing at the “big lake.” Two bald eagles lead the way up the winding road.

We arrive in Cross Village and stop in to see Joann at Three Pines Studio and Gallery. We know we’re in good company when she greets our kiddos with candy canes. The boys enjoy their sweet treats and admire local art while I learn about the gallery’s annual winter solstice event coming up, wondering how I can squeeze another trip up here between now and Christmas.

Then off we go across the street to Black Barn Farm for one of the most memorable parts of our day. We’re there for their Old-Fashioned Christmas. They’re already sold out of sleigh rides for their inaugural December 2018 season (grab spots early for 2019!), and we were lucky enough to get the last seats.

Watching our boys meet Clydesdales Levi and Barney is almost as special as seeing their eyes light up on Christmas morning. And the red sleigh with velvet seats looks just like Santa’s, taking us back in time through the woods of historic Cross Village.

The boys act like Santa’s elves, listening to sleigh bells and holding our hands tightly as the dark-coated Clydesdales carry us across the snow. And right when my husband and I think the boys can’t get any happier, Becky from Highland Roots Farm hands us an apple to feed one of the horses once we get back to the barn.

Over the river and through the woods…hop on one of these 9 Northern Michigan sleigh rides for your own winter adventure!

The boys and I get up nice and close—they have zero fear. I’ll admit, I’m feeling timid being this close to a Clydesdale, knowing as a pair they’re strong enough to pull more than 12,000 pounds. But that fear falls as fast as it came on. We all start laughing hysterically as the Clydesdale chews an apple in my hand, sending chunks toward our faces, sticky juice dripping everywhere. I glance up at my husband just in time for him to capture this moment on camera. The photo will be displayed in our house for many Christmases to come.

Now the sun is landing just right through the trees on our drive back down M-119; it looks like candy cane stripes on the narrow path guiding us south. We are eyeing each Little Traverse Conservancy nature preserve sign along the way, making a wish list for our next trip.

But we have more stops planned for today and are running low on daylight. Little birdies told us if we were traveling to the Harbor Springs area during the holidays, the trip wouldn’t be complete without a stop at Pond Hill Farm. I’m so glad we trusted our friends!

Gnome houses are hidden on groomed snow trails. A sledding hill sits alongside one of the vineyards. Santa’s Workshop is filled with every tool imaginable. There’s a winery. And a brewery.

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My husband and I carry our beverages into the barn with the boys, laughing as they’re chased by ducks. A group of 20-something-year-old guys is sledding and lets us borrow a sled to take our boys down a couple of times. Talk about grinning from ear to ear! We could stay for hours at Pond Hill Farm. And next visit we will.

But the sun is starting to set and we know our boys well enough to realize their good behavior isn’t going to last much longer. By the time we finish our sunset shoreline drive to Petoskey, the sky is dark and the Christmas lights are aglow.

“More, Mommy!” They don’t have to pull my arm to take another lap through downtown—I was going to do it for myself before they even asked. We sing “Santa Claus is Coming to Town,” while looking at the beautiful lights lining the streets.

With our exhausted boys all nestled in car seats, I can’t help but think our toddlers might gift us a silent night. I think about how oh-so-grateful I am that I heeded the little push to experience this snowy world and small-town joy today.

Courtney Jerome, her husband, Josh and their two young boys love playing in the snow surrounding Lake Leelanau. A former award-winning TV producer at WCMU, Courtney has now started her own media company. // Josh Hartman photographs weddings and portraits in some of Northern Michigan’s most iconic landscapes and locales. Born and raised right in the mitten, he has a lifelong appreciation for the Great Lakes.