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 a good dozen orchards, the hidden appeal and agricultural virility, thanks to all the waters, offer the freshest produce and fruit, like apples and pears. Whether you are in for a cozy lakeside retreat, a kayaking adventure, or a family looking to pick their own fruit, there are B&Bs and lakeside lodges for every taste, while the highly-rated Apostle Islands Area Campground is a popular choice to be close to Mother Nature. For local culture and attractions, Manypenny Bistro and Bayfield Maritime Museum are not-to-be-missed, while Bayfield also hosts many events in the summer, like free concerts by the lake for bluegrass and rock fans.
Chesterton, Indiana
Chesterton, a Northwest Indiana town, is a quintessential gem in the Great Lakes Region. Just one hour from Chicago and minutes from the southernmost shore of Lake Michigan, visitors enjoy immediate access to Portage Lakefront & Riverwalk and Porter Beach for leisure. Adventures are just minutes away at the infamous Indiana Dunes, thousands of years in the making by Lake Michigan's surf. Comprising no less than 15,000 acres of swept yellow sand and long-bladed beach grasses, visitors can explore the barren yet alive landscape, with shifting shadows under the wind against the lake views, begging 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 serenity as much as a splash of tourist culture, with wineries, historic homes, and hospitality for all other types of travelers to experience the laid-back island lifestyle. There is no better way to explore the island than a bike or a golf cart rental, a hike through the state park, or a simple fishing charter to catch perch or walleye. Don't miss the Native American petroglyphs in a limestone boulder, while the downtown drums to an island pace with gift stores, restaurants, and 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 are in for a quick escape or a weeklong getaway from the city, there is something for every group, including hiking, fishing, a marina, and Kewaunee Lighthouse, a museum. The fresh lake breeze seeps 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 a hand's reach away, defining 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 like biking, the local mode of transportation, and fish stands by the public dock. Offering a variety of quality bed & breakfasts, hotels, and inns, wind down your style or enjoy camping under the stars along a sandy beach and wake up for a summertime morning dip before a new set of activities. Families enjoy visiting over 100 animals at Old McDonald’s Farm Village, while art and culture fans appreciate Pickering Beach Museum and the Arts Association of Northern New York. Sackets Harbor Heritage Area Visitor Center offers striking exhibits and guidance to make the most of your time, including a 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 entice the kids and kids-at-heart, while those who know St. Joseph go straight to White Pine Winery for a tour and tasting. Basking in its underappreciated privileges, the town stays pristinely quiet and natural, with rustic charm even in the high season. Whether you are more of a beach lover without crowds or a hiking type through Tiscornia Park to the majestic St. Joseph Lighthouse, it is all drenched with simplicity and authenticity—pure 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 score a real piece of art, enjoy quintessentially North-Shore-inspired attractions like Burlington Bay Campground, and meet curious locals, including the big-lake fishermen, the iron-ore miners, loggers, and artists at Burlington Station. Prevailing with the spirit of the wilderness, embark on a scenic hike through the Gooseberry Falls forest with a number of refreshing waterfalls or sand dunes to hunt for fresh agate. The breathtaking Agate Bay Beach feels made for lazy swims and relaxation, while the active types 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.
