By J.P. Anderson By J.P. Anderson | December 20, 2023 | Lifestyle, Feature, Guides,
A little over an hour’s drive from downtown Chicago, Harbor Country, Mich. is one of the region’s most popular weekend destinations, and with good reason: From picturesque Lake Michigan beaches to award-winning breweries and wineries and more, the area’s eight charming towns offer countless delights all year round. Here, our essential spots for the ultimate weekend in Harbor Country.
Where To Eat
30 N. Whittaker St., New Buffalo, Mich. / Website
New Buffalo’s go-to breakfast and lunch spot, this welcoming counter-service joint draws a lively crowd for morning java, homemade pastries and seriously delectable sandwiches—including a crave-able Reuben in corned beef, turkey or veggie varieties, all delish.
3311 Pottawattomie Trail, Michigan City, Ind. / Website
Sinatra’s on the stereo and chef Joe Farina’s crowd-pleasing Italian steakhouse fare is on the menu at this always-buzzing see-and-be-seen spot. Grab a dirty martini at the packed bar and people-watch while you wait for your table—the vibe alone makes it worth the trip.
19 N. Elm St., Three Oaks, Mich. / Website
Shelves lined high with jams, jellies and preserves plus displays of home decor, gifts and various kitsch greet visitors to this expansive space in the heart of Three Oaks, but the real reason to visit is the homey cuisine turned out by the open kitchen, from signature pickle-brined fried chicken sandwiches and mac-n-cheese hand pies to crispy pan spaghetti and brunch faves like ham-and-cheese-stuffed French toast with blueberry jalapeño jam on the side.
See Also: The Ultimate Guide To Mackinac Island
Photo by Moguel Photography
5851 Sawyer Road, Sawyer, Mich. / Website
A comfortably chic vibe and a creative menu from Le Cordon Bleu-trained Chicago transplant Mike Kinasz (think risotto carbonara with quail egg and Great Lakes whitefish with maitake mushrooms) have quickly made this homey spot in the old Flynn Theatre a favorite destination.
111 W. Water St., New Buffalo, Mich. / Website
This special occasion spot on the water in downtown New Buffalo beckons with a romantic harborside terrace and a fine Italian menu—think pepper-crusted beef carpaccio, risotto studded with trumpet and beech mushrooms, and seafood cioppino with grilled ciabatta.
16409 Red Arrow Highway, Union Pier, Mich. / Website
Asian flair meets old-school vibes in this special occasion fave from chef Timothy Sizer, whose menu offers crowd-pleasing fare ranging from addictive bang bang shrimp and lemongrass chicken to classic plates of fish and chips and peppercorn-crusted filet mignon.
Where To Stay
111 W. Water St., New Buffalo, Mich. / Website
The go-to for luxury lodging in New Buffalo, this stylish property boasts primo waterfront location and a top dining destination in the Terrace Room.
9708 Berrien St., Union Pier, Mich. / Website
With just 16 rooms and located steps from the beach, this quaint inn is a quiet respite with an ideal location from which to explore the surrounding towns.
On The Town
107 Generations Drive, Three Oaks, Mich. / Website
Set in the former Warren Featherbone Company building in downtown Three Oaks adjacent to Journeyman Distillery, this intimate live music venue opened in 2003 and has hosted acts ranging from Jeff Tweedy and The Cowboy Junkies to opera star Nathan Gunn.
Photo by Moguel Photography
30 N. Whittaker St., New Buffalo, Mich. / Website
On evenings from Thursday to Monday, David’s Delicatessen & Coffee transforms into this haven of expert mixology, where you can find libations worthy of just about any big-city craft cocktail bar. Start with the classic False Front Manhattan, then let your bartender (and the extensive menu) be your guide.
5885 Sawyer Road, Sawyer, Mich. / Website
Order a snifter of housemade bacon and settle in at this beloved downtown Sawyer hangout, which serves up its own award-winning brews alongside a full menu of barbecue, fried chicken, gumbo and more.
109 Generations Drive, Three Oaks, Mich. / Website
This distillery at the Featherbone Factory is on a roll, having been named 2023 Craft Distillery of the Year and awarded best whiskey for two consecutive years at the American Spirits Council of Tasters (ASCOT) Awards. They’ve just opened a $40 million campus in Valparaiso, Ind., but home base remains in Three Oaks, where they draw crowds for tours and tastings, the buzzing Staymaker restaurant and the 30,000-square-foot Welter’s Folly 18-hole public putting green.
245 N. Whittaker St., New Buffalo, Mich. / Website
Touristy? Yes. Crowded? Always. But with prime location near the water in downtown New Buffalo, this all-American bar and grill is still worth an in-season visit for its hopping rooftop scene and its killer tavern burger, which gives iconic joint Redamak’s up the road a run for its money.
Where To Shop
14 N. Elm St., Three Oaks, Mich. / Website
Plenty of Harbor Country shops go all in for the lakeside aesthetic (think “Beach This Way” signs and corner-store kitsch), but not this sophisticated space from Chicago transplant Marco Chaverry, whose impeccable taste in furniture, textiles, art and home accents shine through in every hypercurated vignette. Also be sure to check out his new Alapash Mercantile at 111 N. Elm St. on the Featherbone Factory campus for plants and more.
100 N. Whittaker St., New Buffalo, Mich. / Website
Open just since summer 2022, this artfully curated, coastal-inspired lifestyle shop has fast become a go-to for books, home decor, gifts, beach accessories and more.
Photo by Moguel Photography
2 Maple St., Three Oaks, Mich. / Website
At this charming wine nook, Pat and Ellie Mullins (also proprietors of Patellie’s Pizza around the corner) stock a thoughtful, handpicked selection of boutique old and new world bottles.
5865 Sawyer Road, Sawyer, Mich. / Website
From a bounty of locally grown produce to an expansive selection of garden supplies, gourmet food items, apparel, home decor and more, this always-buzzing emporium is one of Harbor Country’s essential shopping spots.
What To See & Do
111 W. Water St., New Buffalo, Mich. / Website
From seaweed facials and sugar and lavender body scrubs to massage and more, this spa looking out onto New Buffalo harbor at the Harbor Grand Hotel focuses on marine botanicals in all of its luxe treatments.
17424 Red Arrow Hwy., New Buffalo, Mich. / Website
Lake Michigan is the main natural attraction in these parts, but this lush 86-acre green space is also worth a visit thanks to its easily navigable 300-foot canopy walkway and 600-foot marsh boardwalk leading to river viewing and fishing platforms.
10983 Hills Road, Baroda, Mich. / Website
No visit to Harbor Country would be complete without a visit to one of its wineries, and this buzzing destination—centered around a turn-of-the-century Amish round barn and offering tastings, live music and events galore—is the perfect place to sip and swirl.
12032 Red Arrow Hwy, Sawyer, Mich. / Website
Boasting three miles of Lake Michigan shoreline, kayak and SUP rentals and two campgrounds against the backdrop of majestic 260-foot-tall sand dunes, this 1,500-acre destination is Harbor Country’s top spot for experiencing the lakeshore.
Photography by: Reuben photo by Chris Mullins/cmullinsphotography.com; pasta photo by Jason Palermo; pantry photo by Matthew Kirby; Acorn photo by borterwagner photography; Warren Dunes photo by Getty Images/Single-Tooth-Productions; Susan’s/False Front/P+E Bottle Shop photos by Moguel Photography, a lifestyle and portrait photographer based in Southwest Michigan—find his work at moguelphotography.com.