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  Lake Michigan Weekend: These Small Towns Are Chicago Road-Trip Worthy © Provided by TheTravel

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  • Beachy, Relaxed Vibes In New Buffalo, Michigan
  • Porter, Indiana: Get Outdoors At This National Park
  • Sturgeon Bay Is A Cozy Wisconsin Wonder
  • An Artsy, Lakeside Gem In Saugatuck, Michigan
  • Dutch Culture Rules In Holland, Michigan

What could be better than a lakeside retreat complete with beautiful beaches, a small town, friendly vibes, and relaxed settings that just scream summer? All this (and more!) can be found at one of these Lake Michigan beauties—close enough to Chicago to make for a weekend getaway, yet far enough away to feel like a real escape from the city.

And while the real-deal Great Lakes Circle Tour takes about 15 long hours to complete, there are a myriad of other ways to explore these remarkable Lake Michigan gems, all without having to spend half the day in the car. These beachy towns are just waiting to be explored—whether it’s two towns for the price of one in Michigan, a one-two Indiana/Michigan adventure, or simply a (long) weekend in Sturgeon Bay, these top towns have something for everyone.

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Beachy, Relaxed Vibes In New Buffalo, Michigan

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Just north of the Indiana border along Michigan’s west coast is the picturesque Lake Michigan shoreside gem of New Buffalo. Known for its expansive recreational harbor, almost 20 miles of lovely beaches, and a reputation for laid-back vibes, this beauty of a beach town was recently mentioned as part of Southwest Michigan's entry on Travel + Leisure’s 50 Best Places to Travel in 2022. Water sports fans will love the abundance of fun on the lake, while beach bums will love the soft, sandy, and scenic beaches of this Gateway to Michigan.

  • Distance From Chicago: About 70 miles
  • Things To Do: Galien River County Park; Four Winds Casino; New Buffalo Railroad Museum; Take a Scenic Lake Michigan Cruise;
  • Where To Eat & Drink: Beer Church Brewing; Redamak’s; Casey’s New Buffalo; Terrace Room
  • Where To Stay: Froehlich’s; The Neighborhood Hotel; Marina Grand Resort; The Harbor Grand Hotel

Porter, Indiana: Get Outdoors At This National Park

Located along the southern shore of Lake Michigan, the town of Porter is famed as the home of the spectacularly sprawling Indiana Dunes National Park—over 15,000 acres of diverse terrain that includes so much more than beautiful beaches and sandy dunes. Home to a diverse ecosystem that includes everything from forests to marshes, Indiana Dunes’ scenic natural beauty is only surpassed by its plethora of outdoor adventures.

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  • Distance From Chicago: About 47 miles
  • Things To Do: Porter Beach; Hike the Little Calumet River Trail and the Great Marsh Trail; Portage Lakefront & Riverwalk Beach; Bike the Dunes Kankakee Bike Trail
  • Where To Eat & Drink: Village Tavern; Wagner’s Ribs; Craft House; Gastro49 Pub & Eatery (Chesterton
  • Where To Stay: Dunewood Campground (at Indiana Dunes); Spring House Inn; Riley’s Railhouse (Chesterton); Dunes Walk Inn at the Furness Mansion

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Sturgeon Bay Is A Cozy Wisconsin Wonder

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Known for its maritime history as both a fisherman’s hub and a ship-building center, the Door County Peninsula charmer of Sturgeon Bay is so much more than its waterside rep—complete with a quaint downtown area, it’s also a scenic spot for a number of outdoor adventures (including bass fishing, of course!)

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  • Distance From Chicago: About 244 miles
  • Things To Do: Stroll through Novel Bay Books; Sherwood Point Lighthouse, Sturgeon Bay Ship Canal Light, and Sturgeon Bay Ship Canal North Pierhead Light; Hike the Ice Age Trail; Door County Maritime Museum
  • Where To Eat & Drink: Melt Bistro (at Renard’s Artisan Cheese); Crate Restaurant; Door County Fire Company; Nightingale Supper Club
  • Where To Stay: Inn at Cedar Crossing; White Lace Inn; The Foxglove Inn; Door County Dragonfly

An Artsy, Lakeside Gem In Saugatuck, Michigan

The small Michigan town of Saugatuck’s stunning natural setting has made it a haven for artists everywhere—but that’s not all. This Kalamazoo River retreat is also home to the Art Institute of Chicago’s Oxbow School of Art, and numerous outdoor art fairs throughout the year, making it a bastion for creatives who want to soak up the eclectic art scene while enjoying the cozy town’s hip, outdoor vibes.

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  • Distance From Chicago: About 141 miles
  • Things To Do: Bike the Blue Star Trail; Saugatuck Center for the Arts; Kayak on the Kalamazoo River; Ride the Saugatuck Chain Ferry
  • Where To Eat & Drink: The Southerner; Bowdie’s Chophouse; Coast 236 Restaurant & Bar; The Butler
  • Where To Stay: Hotel Saugatuck; Starlite Resort; The Kirby Hotel; Lake Shore Resort

Dutch Culture Rules In Holland, Michigan

The lovely Michigan lakeside town of Holland may be famous for its stunning beaches and scenic parks, but it’s the community’s Dutch heritage that makes it truly unique—a heritage that can be enjoyed to this day by visitors looking for bustling vibes and distinctively special attractions. Sunbathe by day on one of Holland’s gorgeous beaches, then head downtown to enjoy the rich tapestry of the cozy streets lined with places to eat, drink, and go Dutch.

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  • Distance From Chicago: About 152 miles
  • Things To Do: Nelis’ Dutch Village; Holland State Park; Catch a spectacular sunset at Tunnel Park; The DeZwaan Windmill and Windmill Island Gardens
  • Where To Eat & Drink: Boatworks Waterfront Restaurant; Hops At 84 East; Seventy-Six; Beechwood Grill
  • Where To Stay: Lake Ranch Resort; The George and Evelyn Suites on 8th; Holland Farm House Inn B&B; Haworth Hotel.

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RELATED: No Car Needed: Spend Summer Vacation On This Michigan IslandLake Michigan is truly a great lake: with an impressive 1,600-mile long shoreline dotted with charming lakeside towns, anyone looking for a weekend escape from Chicago will have their pick of delightful beachy burgs to choose from. Those with more time may opt to head north to explore the scenic Door County Peninsula, while those with an eye for quick shore jaunts may want to stick to Indiana’s lovely coastlines. Either way, these towns are jam-packed with fun, adventure, and beaches galore that make for an unforgettable vacation on beautiful Lake Michigan—the ultimate in relaxation and recreation.

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