A Small Town Christmas

Every year we return to Dudeck’s Pine Country Christmas Tree Farm in Rolling Ridge, Indiana to cut down our Challenger family tree. The fun really starts the day before in Southwest Michigan. There is nothing better than a small town Midwestern Christmas! So, we pack up and head southeast with our extended family to the quaint, picturesque area known as Harbor Country, a collection of lakeside towns often referred to in these parts as The Hamptons of the Midwest!

First stop, the iconic Stray Dog in New Buffalo for lunch. It would not be acceptable to visit Harbor Country and not start with lunch here! The family friendly harborside restaurant has been a staple for almost 20 years, and yes, it’s actually named after a stray dog, Jack. A fire completely burned down the restaurant in 2013, but it was rebuilt with all of the charm of the original location, along with some fabulous new additions such as the adults only roof deck—well used in the warmer months!

The original Stray Dog was adorned with dog photos sent in by patrons. Most of the photos now decorate the bathrooms. In the second stall of the ladies room, you will find a picture of our Golden Retriever Bear and our Bernese Mountain dog Woogie who have both crossed the rainbow bridge but live on. Not to be missed is the retail store next door; it’s the only place where you can buy the coveted Stray Dog logo merchandise. Stray Dog does not have an online store or shop. Come. Sit. Stay. You will be happy you did.

Small Town Christmas

Bear and Woogie featured in the bathroom collage.

New Buffalo is considered The Gateway to Michigan, and is easily accessible from Chicago. Conveniently, they also have an Amtrak stop right across the street from The Stray Dog. We have seen some of the most beautiful sunsets here and love it year round!

Next up, we head to Three Oaks, the arts and cultural center of Harbor Country. The site of the 1989 Christmas classic movie Prancer, Three Oaks is the quintessential small town with a historic main street. The village was first settled by Henry Chamberlain in 1850, and is full of old school charm. December 1st is Small Business Saturday and also the town’s annual Holiday Stroll where the galleries and eclectic shops stay open late offering up extra holiday cheer. Even Santa and Mrs. Claus wouldn’t miss it!

Our friend and interior designer Keek Bielby of Blais Design asked local artist Thomas Allen Pauly if he would show us his newly opened studio and gallery, A Drawing Room, which is closed to the public.

It’s like walking into a Ralph Lauren fantasy—especially for any equestrian or horse lover! Thomas has painted some of the finest horses and jockeys in the country, and his gallery is full of his personal collection of rare books, racing trophies, and jockey silks (all of which sadly are not for sale!). He generously gave us a tour—how thrilling to see where he actually sits and paints his beautiful oil paintings. In particular, I was crushing on the Berner painting, of course.

Thomas Allen Pauly work in progress.

Santa and Mrs. Claus at Poppy Hill Vintage
(where we also picked up a vintage dough bowl!)

Newly opened Froehlich’s, a restaurant, bar, and bakery which occupies the former town pharmacy.

I highly recommend you watch Prancer this holiday season. Even if only to hear Sam Elliot read, “Yes Virginia, there is a Santa Claus.”

Photo from the filming of Prancer in Three Oaks

“Prancer is set in hardscrabble Three Oaks, Michigan, where 8-year-old Jessica Riggs (Rebecca Harrell) still believes in Santa and her widowed father (Sam Elliott) is on the verge of losing their apple farm. Things are so difficult that Jessica’s father decides to send her off to live with an aunt. But shortly before Christmas, Jessica comes across an injured deer—she believes it’s Prancer, one of Santa’s—and begins secretly nursing it back to health so it can help Santa deliver toys on Christmas Eve.” —Newsweek

After a fun filled evening, we check into the Sweethaven Resort, an historic property just off Red Arrow Highway in Union Pier. The country cottages can be your home away from home for one night or a whole week. There is something special about this place year round, especially in the warmer months when you can hop on a resort bike and ride down the road to Lake Michigan. Owners and local experts Linda and Chuck Garasic have owned the resort since the early 90s, and they welcome everyone with open arms and friendly smiles. They’re always ready and willing to help with everything from restaurant recommendations to a glass of wine!

Sweethaven Resort’s newly built Heron House is the perfect spot for our big group. It’s located off the main circle in the woods, and it offers five bedrooms, a full kitchen, fireplace, and most important: a hot tub for the kids!

Movie night at The Heron House.

Just over an hour from Chicago in the rolling hills of Southwest Indiana you’ll find yourself in an evergreen forest at Dudeck’s Pine Country Christmas Tree Farm. Their 80 acre farm has been a family owned and operated business for almost 50 years. 

Hitch a ride on the horse drawn wagon where you can let the driver know what type and size tree you are looking for. After you cut down your tree, be sure to warm up with hot chocolate and tasty treats in the gift shop. Here, you can also find homemade goodies and ornaments to decorate your tree.

We ended up cutting down the first tree we saw! A 13’ Concolor Fir. Concolor Fir trees have a distinctive citrus aroma. They have a soft, silvery blue foliage with flattened needles and stiff branches to hold all your ornaments. This is the third year we went with a Concolor, and we love it!

It took a village to cut down this tree, and then… even more muscle to move it! Good thing my job is “photographer!”

The kids also found a potted tree to bring home. After Christmas, Henry will plant it on our farm where we can decorate it every year!

Last stop on the way home is Stop 50 in Michigan City, Indiana, for their wood fired pizza baked in a 900° hearth oven. Today was their last day of the season before they return in the spring; we got there just in time!

They make a Napoletana style pizza which features a thin, crackery crust. It’s the perfect complement to yummy ingredients like the seasonal pizza with sausage, blue cheese, and carmelized onions. The pie has a slight blackening on the cornicione (outer rim of the crust) which they explain is from the flame kissing the top. Their pizzas begin with dough made from a 20 year old vintage starter: a living, growing dough they feed everyday with flour and water.

Even though we polished off four pizzas, we still ordered a Biga Donut which is essentially a dessert pizza made from fermented dough. OMG it was so good we ate it all before I had a chance to take a picture! Oh, and we ALSO ordered affogatos with their homemade coffee sorbet. It was the perfect closing to our fun filled 24 hours in delicious style! 

Condé Nast recently published their 20 Best Places to Go in 2020 and Southwest Michigan is on the list!

Photo credit: Condé Nast