7 of the Most Overlooked Towns in the Great Lakes
The Great Lakes Region encompasses the towns around its five lakes—Erie, Huron, Michigan, Ontario, and Superior. Defined by waters, its overlooked towns are peaceful, prevailing with a spirit of wilderness to get back to simplicity over authentic attractions on a relaxing escape, often in seclusion. Chesterton is a hop away from the wind-swept Indiana Dunes, while Kelleys Island is home to the Glacial Grooves, the world's largest glacial scoring.
This vast expanse of the Midwest's natural wonder, the lakes, span nearly 100,000 square miles, called "vast inland seas," and comprise nearly 95,000 square miles of water with over 9,000 miles of shore. With the big cities like Chicago and Milwaukee in the region, the smallest towns hidden along the endless shores are often overlooked, where the tiniest of gems have a gigantic hold on the region's boundless recreation opportunities.
Bayfield, Wisconsin
Bayfield, the smallest city in Wisconsin, surpasses all others in the state on Conde Nast Traveler's list as one of the "23 Best Places to Go in the US in 2023." And no wonder—full of attractions well above its leap—the tiny town hidden on the shores in the indent of Lake Superior, the world's largest freshwater lake by area, is an open door into boundless adventures. Home to Apostle Islands National Lakeshore Headquarters, nearby Apostle Islands National Lakeshore comprises a 21-island archipelago with hiking trails, lighthouses, and an extensive network of sea caves to navigate via kayak.
Surrounded by around a dozen orchards, the area's hidden appeal and agricultural strength, thanks to abundant waters, provide the freshest produce and fruit, such as apples and pears. Whether you're seeking a cozy lakeside retreat, a kayaking adventure, or a family outing to pick your own fruit, there are B&Bs and lakeside lodges to suit every taste. The highly-rated Apostle Islands Area Campground is a popular choice for those wanting to be close to nature. For local culture and attractions, Manypenny Bistro and Bayfield Maritime Museum are must-visits, while Bayfield also hosts many summer events, including free lakefront concerts for bluegrass and rock fans.
Chesterton, Indiana
Chesterton, a town in Northwest Indiana, is a true gem in the Great Lakes Region. Just an hour from Chicago and minutes from the southernmost shore of Lake Michigan, visitors have easy access to Portage Lakefront & Riverwalk and Porter Beach for leisure. Adventures are only minutes away at the famous Indiana Dunes, shaped over thousands of years by Lake Michigan's surf. Covering at least 15,000 acres of golden sand and long-bladed beach grasses, visitors can explore the wild yet vibrant landscape, with shifting shadows under the wind and stunning lake views that beg to be photographed.
Often overlooked for larger towns and Chicago, just up the shore to the west, Chesterton takes precedence with its unique geography and water's influence, unmistakable in local attractions and nature. The town hosts its very own Chesterton's European Market, with some 150 vendors selling everything from produce to artisanal bread, crafts, and gifts, held annually as one of the region's most celebrated events in May. The historic downtown area is a family-friendly affair with charming, old-timey attractions like retro-style confectionery. Don't miss the 1882 antiquarian bookstore with rare manuscripts and first editions before settling with a glass into the modern feel of the top-rated Running Vines Winery.
Kelleys Island, Ohio
Home to only 256 year-round residents, Kelleys Island, one of the state's Lake Erie Islands, is a real Ohio oasis dominated by natural areas. The rocky shorelines and lush forests appeal to the outdoorsy, wildlife lovers, and those seeking to get back to simplicity on a relaxing escape. Glacial Grooves, the world's largest glacial scoring, is a fantastic natural landmark for families and photographers. Two hours from Cleveland, including a thirty-minute ferry ride, the easy-going town amid Lake Erie offers attractions for every taste, like Charles Herndon Galleries and Sculpture Garden and Kelleys Island State Park with trails, camping, and a sandy beach.
The welcoming islanders enjoy their peaceful surroundings as much as a touch of tourist culture, with wineries, historic homes, and hospitality for all kinds of travelers to experience the relaxed island lifestyle. There is no better way to explore the island than by renting a bike or golf cart, hiking through the state park, or taking a simple fishing charter to catch perch or walleye. Don't miss the Native American petroglyphs on a limestone boulder, while downtown keeps time with an island pace, featuring gift shops, restaurants, live music, as well as miniature golf and karaoke for entertainment.
Kewaunee, Wisconsin
Kewaunee, an overlooked town overlooking the brilliant blue waters of Lake Michigan, offers "The Good Life on a Great Lake" just north of Milwaukee. Nestled along the western shore between pristine beaches and rolling green pastures, Kewaunee County is a historically agricultural area with natural beauty and small-town charm with an uncrowded feel to explore. Kewaunee, just 40 minutes from Green Bay, is a hidden northeastern gem in the state for outdoor recreational fun, including waterfront town greens.
Whether you're in for a quick escape or a weeklong getaway from the city, there's something for every group, including hiking, fishing, a marina, and Kewaunee Lighthouse, a museum. The fresh lake breeze flows through downtown, which is never overcrowded with attractions like the world's tallest grandfather clock on Miller Street and Hwy. 42/Milwaukee Street. From a stroll along Kewaunee Marshland Walk to shopping and dining near the historic harbor, everything is within reach, embodying this little town's motto of a good life.
Sackets Harbor, New York
While most think of the Big Apple glitz, notable landmarks, and perhaps the Adirondacks, the Great Lakes Region touches the Empire State with some of its most charming towns. Sackets Harbor is all about savoring the good life as one of its 1,351 while kicking back on vacation or a quick city escape. From fine dining restaurants to pubs like Good Fellos and local coffee houses, the local specialty retail and gift shops are just a hop from the northern Lake Ontario shores. Sackets Harbor, a destination for crowdless outdoor pursuits like yachting, fishing, sailing, and windsurfing with a full-service marina, is home to Sackets Harbor Battlefield, where one of the most crucial battles in the War of 1812 took place.
The deeply historic town with preserved architecture along its tree-lined streets charms with authenticity, featuring activities like biking—the local mode of transportation—and fish stands by the public dock. Offering a variety of quality bed & breakfasts, hotels, and inns, you can unwind in your preferred style or enjoy camping under the stars along a sandy beach. Wake up for a summer morning dip before beginning a new set of activities. Families enjoy visiting over 100 animals at Old McDonald’s Farm Village, while art and culture enthusiasts appreciate Pickering Beach Museum and the Arts Association of Northern New York. The Sackets Harbor Heritage Area Visitor Center offers impressive exhibits and guidance to help you make the most of your visit, including a charming village walking tour.
St. Joseph, Michigan
While many unknowingly bypass Michigan's hidden beach resort town, St. Joseph is one of the most charming in one of the country's most beautiful regions. Home to some 7,600 residents affectionately calling it St. Joe, an enchanting blend of coastal bliss and adventures awaits. The fun little town in Berrien County is home to Silver Beach, one of the best in Michigan, the nearby Lions Park, and Silver Beach County Park's crystal-clear waters for sunbathing, lazy strolls, and beach volleyball.
The Silver Beach Carousel amusement park and the refreshing Whirlpool Compass Fountain attract kids and kids-at-heart, while those familiar with St.. Joseph head straight to White Pine Winery for a tour and tasting. Enjoying its often overlooked charms, the town remains peacefully quiet and natural, with rustic appeal even during the busy season. Whether you're more of a beach enthusiast seeking solitude or a hiker exploring Tiscornia Park to reach the majestic St. Joseph Lighthouse, everything is infused with simplicity and authenticity—true seclusion.
Two Harbors, Minnesota
Although quite a hotbed for agate hunting, this Lake County town enjoys staying quaint and small along the stunning Lake Superior. Exuding calmness and historic allure, Two Harbors draws fishermen, beachcombers, and outdoor enthusiasts in general. Offering a quiet escape, visitors can discover the laid-back northern Minnesota culture on par with small-town businesses. From cozy shops and cafes like Vanilla Bean to historic sites and landmarks, in between adorable gift shops, the clifftop Split Rock Lighthouse is unmissable.
Visitors can browse through crafts and acquire a genuine piece of art, enjoy quintessential North Shore-inspired attractions like Burlington Bay Campground, and meet curious locals, including big-lake fishermen, iron-ore miners, loggers, and artists at Burlington Station. Embracing the spirit of the wilderness, embark on a scenic hike through the Gooseberry Falls forest, where you can find refreshing waterfalls or sand dunes to hunt for new agate. The stunning Agate Bay Beach feels perfect for lazy swims and relaxation, while active visitors can take on the waters with a kayak or paddleboard.
The Great Lakes Region is a world-sought destination in the American heartland to taste the waterside life and an easy escape for Midwesterners hankering for a beachfront vacation or getaway. Bayfield, for example, Wisconsin's smallest city, is an open door into the 21-island archipelago Apostle Islands National Lakeshore, with hiking trails, lighthouses, and an extensive network of sea caves for kayaking. Truly underappreciated, the small towns lost amid the mind-boggling bodies of freshwater, like seas without the salt content, hold the promise of rewarding opportunities.
