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U-pick fruit farms and super-stylish homegoods stores, vertiginous dunes and high-gravity beers: this is Harbor Country, a strand of eight charming towns on the eastern shore of Lake Michigan. Spanning just 15 miles, Harbor Country can be traversed by car in mere minutes, but if you slow down and look around, you’ll find sufficient outdoor adventures, eclectic shopping opportunities and excellent dining and drinking spots to delight you for a weekend – or, in the case of the burned-out urbanites who have permanently decamped here from nearby Chicago, for good.

Get your bearings

The communities comprising Harbor Country were predominantly established as logging towns by enterprising mid-19th-century businessmen and pioneers who guessed that nascent Chicago, busily shooting up just across Lake Michigan, might have some use for southwestern Michigan’s virgin forests. Local tourism began to pick up steam with the arrival of trains and, later, a highway system connecting the region to cities in the Great Lakes and beyond. (There’s perhaps no more fitting indicator of the area’s history as Chicago’s favorite getaway than its alleged popularity with Al Capone.)

Today, the towns of Harbor Country are like siblings. They share an underlying DNA that mingles easy-going rusticity with the cosmopolitan influence of big-city visitors, but each has its own quirks to distinguish it. With its galleries and of , artsy Three Oaks (five miles east of the lake and the sole inland member of the group) is cultured, but doesn’t take itself too seriously. Harborside New Buffalo is the most built up – and accordingly, the least quaint – but the tradeoff is lots of walkable shopping and dining, plus the area’s poshest lodging options, like the Frank Lloyd Wright-inspired and its Scandi-styled sister property, the .

Union Pier is home to wine-tasting rooms and Dirty Dancing-worthy cottage accommodations like the . Boutiques like distinguish Lakeside as a stronghold for fashion and design tastemakers, while Harbert celebrates its Nordic roots with sweet spots like . Craft beer-loving Sawyer, the northernmost link in the Harbor Country chain, gives off a good-time vibe; even the town sells local suds. (The remaining two towns, Michiana and neighboring Grand Beach, are the area’s quiet southerly twins. Unless rubbernecking at vacation homes is a passion, you likely won’t find reason to linger long in either.)

Climb dunes, hang ten and conquer the century

In fine weather, opportunities abound to explore Harbor Country’s natural splendor. The area’s marquee feature is, of course, its expansive lakefront. If you’re game for a good stretch of the legs, set aside an early evening to scale the formidable 240-foot sand dunes at Warren Dunes State Park in Sawyer; you’ll be rewarded with sweeping sunset views.

If you think catching waves is a saltwater-only pursuit, the lake surfing apostles at New Buffalo’s Third Coast Surf Shop have news for you: Lake Michigan’s got a respectable surfing game. From private lessons to gear rental, they’ll set you up with everything you need to hit the waves. It might not be The Endless Summer, but it’s certainly an unexpected way to experience the Great Lakes.

Come autumn, when the humidity eases and the leaves begin to put on a fiery show, there’s no better way to tour Harbor Country’s tranquil backroads than on a bike. Dewey Cannon Trading Company in Three Oaks is the region’s best cycling resource (not least for its endearingly moth-eaten bicycle museum). The shop can outfit you with a rental and provide you with information about the region’s many bike routes. It’s also the kickoff spot for the long-running , a popular non-competitive 100-mile ride held each September.

Grab a bite

Close proximity to a spoil of farms means that Harbor Country’s best dining spots were doing the locavore thing long before it became a buzzword, and without an ounce of pretension. Three Oaks favorite makes mornings happy with handmade bagels and turnovers bursting with Michigan cherries. For a take-home taste of the Great Lakes, peruse the impressive selection of pickles and preserves.

Union Pier’s lovely is the stuff romantic picnic dreams are made of. Stop in for made-to-order sandwiches on rustic bread, plus cheese board fixings, flaky fruit kolaches, and chilled rosé. Lakeside boasts the region's classiest seafood shack, – owner Rachel Collins’ prior experience includes developing a freshwater caviar line. Pop by for al pastor-seasoned cod tacos and smoked salmon BLTs, best enjoyed within earshot of lapping waves.

Dinner comes with a nautical views at the , which overlooks New Buffalo’s pleasure boat-packed marina. Pull up a seat on the patio and dig into elevated pub fare like wood-fired prosciutto and fig pizza and roasted crimini-topped steak frites. For a sweet finish, stroll over to nearby , equally beloved for its 50+ flavors of locally-produced ice cream and its kitschy porcine decor (think head-in-hole photo ops featuring swimsuit-clad porkers and ‘I just made a pig of myself at Oink’s’ button pins).

Pick your poison

No waterfront getaway is complete without a sundowner or two, and Harbor Country has homegrown libations in spades. Hop heads should make haste for Sawyer, where at busy times – that is, just about all day, every day in summer – ’s patrons seem to take over the town’s main drag. The taproom is often at capacity (thank popular brews like easy-drinking IPA Star Chicken Shotgun plus darned tasty barbecue), but you can while away your wait with bocce ball and sausage at the outdoor annex across the street.

A note of irreverence flavors the offerings at , a microbrewery housed in an erstwhile Methodist church whose incongruous facade – bold red lettering proclaiming BREWERY beneath a pristine white steeple – is one of New Buffalo’s most Instagrammed landmarks.

If stiff drinks are more your speed, head to Three Oak’s Journeyman, an organic distillery situated in a beautifully restored 19th-century factory that once produced corsets and buggy whips. Tours are held on weekends, and offer a chance to sample the distillery’s creative output, like bilberry gin and 100% wheat whiskey. Leave time for cocktails, smoked trout spread and bourbon-laced crispy pork belly at Staymaker, the top-notch onsite restaurant.

Union Pier plays host to a satellite location of Round Barn, one of the area’s most popular wineries; tastings are offered daily. (Note that fruit wines and sweet reds feature heavily in the lineup.)

Something old, something new

On the shopping front, Harbor Country has an eye for design that runs the gamut from avant-garde minimalism to shabby-chic antiques. A trio of boutiques – Three Oaks’ , Lakeside’s and Sawyer’s – stock just about everything you need to live your coolest life, from design books and quirky art prints to Nordic-influenced ceramics and artisanal textiles.

Traditionalists should plan for a leisurely afternoon in Three Oaks. Admire jewel-toned antique rugs and a carefully curated selection of furniture and pottery at Mazet, and browse the day’s vintage treasures – think retro signs, crates of vinyl and vintage enamelware – at .

Make it happen

Summer and (to a lesser extent) autumn draw big crowds to the area, especially on weekends; to minimize frustration, book accommodation in advance and anticipate traffic. I-94 efficiently links the towns of Harbor Country, but for a real taste of the local vibe, there’s no substitute for the rambling Red Arrow Highway, which traces a similar route, but with a distinct backcountry flavor. from Chicago and Detroit service New Buffalo.

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