Head out of Chicago toward Michigan, and as soon as you cross the state line you are in Harbor Country. Just like that, you’ve left the hustle and bustle of the city behind and you can slow down, relax and enjoy all that this Lake Michigan region has to offer. During the warm-weather months Harbor Country may be packed with visitors, but as summer wanes so do the crowds, making the southwest corner of Michigan perfect for a tranquil, long weekend getaway.

The time is ripe for fall colors, antiques shopping, sampling local culinary delights and getting cozy by a fire. When winter sets in, witness how nature creates sculptures from the wind, ice and snow. Harbor Country’s eight towns each have their individual appeal; together they add up to a Great Lakes getaway. And you have to venture just 90 minutes from downtown Chicago to experience it.


There is an abundance of exceptional food in the southwest corner of Michigan, from market finds to fine waterfront dining.

Whistle Stop Grocery serves up seasonal and local flavors. Sip a specialty coffee with a breakfast or lunch sandwich, and shop the gourmet market for staples and specialty foods.

Red Arrow Roadhouse, a local favorite and weekend gathering place with a casual vibe in a knotty pine setting, is known for its BBQ Baby Back Ribs, rib mac & cheese and other twists on American traditional foods.

For something more upscale and romantic, choose the newly remodeled Terrace Room at The Harbor Grand for authentic Italian cuisine. Dine by the fireplace while enjoying harbor views.

After dinner head to Oink’s—fully decorated in every type of pig decor you could possibly find—for a choice of over 55 flavors of hand-dipped ice cream and yogurt (open through mid-November).


Leave the interstate and cruise the Red Arrow Highway for a closer look at fall color. The road meanders along the Lake Michigan shoreline past inviting antique stores, fruit stands and boutique shops. Or follow the Harbor Country Driving Tour at harborcountry.org.

Head to Doe-Wah-Jack’s for a leisurely paddle on the Dowagiac River, or rent two wheels at Dewey Cannon Trading Company and follow a choice of 20 Backroad Bikeways trails.


Pick up fixings for a fall picnic at Froehlich’s, famous for their homegrown preserves, jams, fruits and vegetables as well as homemade breads and pastries and extensive deli menu. Don’t miss Drier’s Meat Market, in continuous use as a butcher shop since the late 1800’s. It’s on the National Register of Historic Places and worth a stop simply for the nostalgia—but you’ll want to add house smoked meats, jerky, smoked fish spreads or even popcorn to your picnic basket. Local in New Buffalo lives up to its name with locally produced and grown meats, cheeses  and produce, plus a small selection of fresh baked breads and specialty foods.


Michigan is one of the Top 10 wine producing states in the nation and a visit to Harbor Country gives you the chance to sample and savor not only award-winning wine but craft beer and small batch spirits, too.

Stops along the Lake Michigan Shore Wine Trail include Harbor Country’s Round Barn and Lemon Creek wineries and Baroda Founders Wine Cellar. At St. Julian Winery the family of founder Mariano Meconi has been perfecting the art of winemaking since 1921.

Tour Journeyman Distillery to see how whiskey is made in the former Featherbone Factory. Journeyman is one of the few organic and kosher distilleries in the U.S. Famous for their small batch organic rye whiskeys, they are now also handcrafting small batches of gin, vodka, rum and a few other specialty spirits. miwinetrail.com


In an area long known for great vintage finds, there has been a “boom in antique stores in the last two years” says Viki Gudas, executive director of the Harbor Country Chamber of Commerce. A local favorite is Trilogy in Three Oaks, a cooperative store housed in a former bowling alley. Unique finds pop up at Blue Moon Vintage Market, held the fourth weekend of each month in Three Oaks. Plan to spend time browsing the area’s art galleries and independent gift and clothing boutiques.

Pick up local produce at John’s New Buffalo Farmer’s Market on W. Buffalo, and find a wide selection of craft beer, wine and specialty foods in the old world atmosphere of the adjacent Promeny  Olive & Wine shop. On Saturday mornings enjoy Skip’s European Farmers Market and browse the colorful display of locally grown fruits, vegetables, flowers and local artisan wares.


For an entertaining evening in Three Oaks, catch a live performance at the Acorn Theater or a movie at the Vickers Theatre, a 100-year-old classic art house and cinema that showcases independent and foreign films (closes for five weeks in January).

At Four Winds Casino Resort in New Buffalo you can dine, take in a live show and play the slots and table games in a setting of natural materials designed to evoke the traditional lodges of the Pokagon Band of Potawatomi Indians, which owns and operates the casino.


Spending time outdoors in the winter has its own special charm. There is a peacefulness when the land is blanketed in a cover of white. Dress warmly and head to the Lake Michigan shoreline to view the ice and snow sculptures formed by Mother Nature, or strap on your snowshoes or cross-country skis and hit the trails found throughout the area, including Warren Dunes State Park.


For a cozy night’s sleep, check into The Harbor Grand, a 54-room boutique hotel in downtown New Buffalo, right on the harbor and a short two-block stroll from the beach. Request a fireplace room with a harbor view and enjoy lazy mornings and complimentary breakfast in bed. There’s an indoor pool and guests of the hotel are welcome to borrow a bike to ride to the beach, along the lakeshore or through town. As a bonus, The Harbor Grand has Ben & Jerry’s ice cream on demand 24/7.

This article originally appeared in the 2016 fall/winter issue of Experience Michigan magazine. The contents of this article were checked for accuracy when it was published; however, it’s possible some of the information has changed. We recommend you call first if you have specific questions for the destinations, attractions or restaurants mentioned in this article.

No portion of this article or magazine may be reproduced without prior written permission by the publisher.


Deb Thompson shares tales of girlfriend getaways, solo travel and wine and culinary experiences. She creates travel content at justshortofcrazy.com and is the co-owner of Social Influencer Media.

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