Sunset on Fishtown, Leland, Michigan.

8 of the Most Quaint Small Towns in the Great Lakes Region

When most people think of coastal vacations, their minds immediately spring to the beach resorts on the Pacific and Atlantic Oceans. However, right in the middle of the continent, there is a region that has all the joys of coasts, along with an array of natural features that only exist alongside the beautiful Great Lakes. While cities such as Chicago and Cleveland sit on the mighty shores, they are missing some of the charms only available in the small quaint towns in the region.

Winthrop Harbor, Illinois

Looking out over the water at sunset, Winthrop Harbor, Illinois Marina.
Winthrop Harbor, Illinois Marina.

On the western shore of Lake Michigan, about equidistant between Milwaukee and Chicago, is the village of Winthrop Harbor. Sometimes called the cornerstone of Illinois, the town is a perfect spot to experience the glory of the great lake it sits upon while avoiding the crowds of the metropolises that border it.

Winthrop Harbor has access to great trails, such as those within the Illinois Beach State Park, which allow hikers to see the wetlands of the Ramsar Area, as well as those in the ravine at Novotny Park. To experience the lake, visitors should not miss the sandy expanses at North Point Beach, located just north of one of Winthrop Harbor’s most iconic landmarks: the North Point Marina. The marina is the largest one on any of the great lakes and sets Winthrop Harbor apart.

Grand Haven, Michigan

Red Grand Haven South Pierhead Inner Light, built in 1905, Lake Michigan.
Grand Haven South Pierhead Inner Light, Lake Michigan.

Across the lake from Winthrop Harbor in the state that shares its name with Great Lake Michigan is the adorable town of Grand Haven. And if the former is known for its stunning marina, Grand Haven is known for its sandy beaches. North Beach Park, Grand Haven State Park, and the Grand Haven Dog Beach are all attractive and offer a beach experience for every type of traveler.

Running along the beaches, the harbor, and past many of the shops in Grand Haven is 2 ½ miles of boardwalk, taking walkers to many of the sights of the town. One of these sights is the famous Grand Haven Lighthouse in its one-of-a-kind red coat of paint. Another of the town’s icons is the Grand Haven Musical Fountain, which gives special performances of synchronized water, music, and light every evening at dusk from May through September.

Leland, Michigan

Main street in Leland, Michigan, also known as Fishtown, originally a fishing community, now a tourist destination with restaurants, quaint shops and boutiques.
Main Street in Leland, Michigan. Image credit Frank Setili via Shutterstock.com

For a completely different way to experience Lake Michigan than the sandy beaches of Grand Haven, the old fishing village aura of Leland might be right up your alley. Historic Fishtown, a collection of shanties, tugboats, and old docks, is the perfect spot to experience the maritime lineage of the Great Lakes region, and thanks to ongoing preservation efforts, it is still in pristine condition.

Another way to experience the region's history is to hop on a ferry to the Manitou Islands, which technically lie within the borders of Leland. Ghost towns, sand dunes, and lighthouses await travelers on these jewels of Lake Michigan. On the mainland, there is the Whaleback Natural Area and the Clay Cliffs Natural Area for those looking to delve into the natural landscapes surrounding Leland.

Munising, Michigan

Aerial view of Munising, Michigan, in winter.
Overlooking Munising, Michigan, in winter.

For even more gorgeous natural beauty, it would be hard to do better than Munising. Straddling the same-named bay on Lake Superior, the underrated town radiates the majestic beauty of the Great Lakes region. The standout of its many features is the Pictured Rocks National Lakeshore. Walls of the mineral-stained stone tower at times 200 feet above the tides of the Great Lake in shades of red, orange, blue, and green.

Beaches and miles of trails allow for a thorough exploration of the Lakeshore, which also contains waterfalls and lighthouses. Munising also has access to the magnificent Hiawatha National Forest, popular for hiking, camping, and picnicking.

St. Joseph, Michigan

Aerial view of the St. Joseph North and South Pier Lighthouses on Lake Michigan
St. Joseph North and South Pier Lighthouses on Lake Michigan.

St. Joseph is a quaint and cozy destination on the southern shores of Lake Michigan. It is home to the gorgeous Silver Beach, renowned for being among the most idyllic beaches in the entire Great Lakes region, as well as the North and South Pier Lighthouses, which are perfect emblems for the romance of the area.

St. Joseph is also home to a thriving arts community, and the spirit of creativity is palpable in the air. The Krasl Art Center is a must-visit gallery for anyone looking to take in some truly great art, as is the Box Factory for the Arts.

Traverse City, Michigan

Traverse City Film Festival on the marquee at The State Theatre on Front Street.
Traverse City Film Festival on the marquee at The State Theatre on Front Street. Image credit Cory Woodruff via Shutterstock

Once voted the "Most Beautiful Place in America," Traverse City is a jewel of the Great Lakes region. The town is a destination in both the summer and winter months, featuring all that its shoreline location grants, as well as close access to ski hills and trails. It also has the distinction of being surrounded by fruit production and is the country’s leading producer of sour cherries. Wineries, vineyards, and a thriving craft beer culture are sure to keep both the connoisseurs and the merely curious immensely satisfied.

The West End, Volleyball, and Bryant Park beaches allow for immediate shore access to Lake Michigan’s Grand Traverse Bay, and the Boardman Lake Trail gives walkers the opportunity to see a much smaller, though no less great lake within the town limits.

Chesterton, Indiana

The amphitheatre and Philips Pond at Coffee Creek Watershed Preserve.
The amphitheatre and Philips Pond at Coffee Creek Watershed Preserve. Image credit Smith Donovan via Shutterstock.

On the south shore of Lake Michigan is the town of Chesterton. The town is home to a distinctive tight-knit culture that celebrates its own art and culture, and features sites like the Westchester History Museum, the Chesterton Arts Center, and the Commercial Historic District. In the summer, the town hosts an outdoor European Market, which features artisanal goods such as local produce and crafts, and in the winter, there is the holiday-themed Mistletoe Market.

Chesterton also boasts proximity to the Indiana Dunes and the state and national parks accompanying it. Rolling hills of wind-shaped sand line the southern coast of the Great Lake, creating a unique and historic landscape that is rich in compelling beauty. Distinct vegetation fills the parks, as do a variety of fascinating wildlife. Hiking, beachcombing, picnicking, and even cross-country skiing are all available in the region, and Chesterton is the ideal anchor for a trip.

Bayfield, Wisconsin

People enjoy the Annual Applefest in Bayfield, Wisconsin
Annual Applefest in Bayfield, Wisconsin. Image credit Jacob Boomsma via Shutterstock

Bayfield offers a unique way to experience the Great Lakes region. Situated on the north section of Chequamegon Bay in Lake Superior, the town has close access to the Apostle Islands. A day spent on any of the peninsula’s idyllic beaches gazing upon the majesty of the islands is just one way to soak up the magic of the area. Guided kayak tours of the islands are another, and there are tours that suit every experience level of kayaker.

Yet another way is by a slightly bigger boat, whether that is the Apostle Island Cruise, which offers several tours exploring different parts of the islands, or the ferry that takes travelers to Madeline Island, the biggest of the bunch. Local artisan shops, the Bell Street Gallery, and the Big Bay State Park are all worth visiting on Madeline Island, whether you are taking a day trip or deciding to spend the night camping on the island.

The Great Lakes region has some of the most beautiful sights in the entire country. With golden beaches, rugged coastlines, thick forests, and even sand dunes, there is no lack of stunning things to see. Whether you are looking for a relaxing day lounging by the waves or an exciting excursion on a remote hiking trail, the region surrounding the Great Lakes has something to offer.

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