The Most Charming Lakefront Towns in Southwest Michigan

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Michiganders seeking a special weekend getaway will find plenty of amazing options in Southwest Michigan. Known for its scenic waterfront towns and natural beauty, this region offers something for everyone. From the charming lakeside towns of St. Joseph and South Haven to the bustling art and wine scene in Saugatuck, Southwest Michigan is perfect for a relaxing retreat or an outdoor adventure.

Outdoor enthusiasts can enjoy hiking, kayaking, and exploring the shores of Lake Michigan, while foodies will love discovering the region’s wineries, breweries, and farm-to-table dining experiences. With its picturesque landscapes and small-town charm, Southwest Michigan promises unforgettable memories for travelers of all interests and ages. Whether you’re planning a romantic escape or a family trip, Southwest Michigan is ready to welcome you!

New Buffalo, MI

Just 70 miles away from downtown Chicago is New Buffalo, a lovely beach town situated between Lake Michigan and the Galien River. Known as the gateway to southwest Michigan’s beaches, New Buffalo is home to the most modern freshwater refuge harbors on Lake Michigan. Boats and watersports abound, with some of the best salmon, perch and trout fishing to be found in the midwest. Locals and vacationers can spend the day golfing or browsing art galleries, shops and grabbing a pastry or sandwich at the famous Froelich’s in town before strolling to the New Buffalo Beach and Lions Pavilion Park over wooden walkways and across towering sand dunes. The shimmering water of Lake Michigan invites swimmers, paddle-boarders and kayaks to its sandy shores. New Buffalo is nothing if not friendly to hikers and cyclists and is perfect for picnics.

The Best Downtowns in Michigan Harbor Country

Grand Haven, MI

It’s easy to fall in love with the Grand Haven area, and that is why it attracts so many year-round return visitors. With its award-winning beaches, biking, hiking and a lakeview trail winding through wooded dunes at Rosy Mound Natural Area, midwestern folks from all over flock to Grand Haven for rest, relaxation and rejuvenation. Downtown is dotted with historic architecture worthy of exploration, and the boardwalk that runs along the harbor to Grand Haven State Park Beach is lined with restaurants and unique shops of all kinds. For camping, lodging, picnicking and general R & R in nature, Grand Haven State Park is a sprawling 48 acres set mainly along the sandy Lake Michigan shoreline, with scenic views of the Grand Haven Pier and two historic lighthouses.

South Haven, MI

Yet another perfect weekend getaway on the eastern side of Lake Michigan is the universally beloved city of South Haven, where watersports reign supreme off of the sunset coast. Seasonal boaters of all kinds are welcome to dock in the Black River Harbor, and canoeing, kayaking and jet skiing are king in this slice of paradise. Visitors can choose to lodge in any number of styles–from camping to cottage rentals, historic hotels and quaint bed and breakfasts. South Haven is buzzing with live music festivals, arts, culture, and bounteous and diverse eateries, all year around. Michigan is not stingy with their sunsets, so don’t forget to spend that golden time of day with your eye on the horizon for a breathtaking and memorable experience.

Saugatuck, MI

Whether you’re looking for a weekend escape or a picturesque place to call home, Saugatuck seamlessly blends culture and nature, offering the perfect destination for both relaxation and inspiration. Downtown Saugatuck offers the perfect blend of sunny beach days, thrilling watersports, dune buggy adventures, delectable dining, and a vibrant arts scene—all wrapped up in a charming small-town atmosphere. While Saugatuck delights year-round, September is a hidden gem for visitors. Thanks to its unique microclimate, the beaches remain warm and pleasantly uncrowded as the area begins its transition into fall. For those who love autumnal activities, Saugatuck truly shines in the fall. Stroll through the breathtaking changing leaves at Mount Baldhead Park or soak in the stunning seasonal scenery aboard the Star of Saugatuck paddlewheel boat. Apple picking enthusiasts will find even more reasons to visit during this time of year.

Downtown Saugatuck MI

Union Pier, MI

Situated in southwest Michigan between the clear waters of Lake Michigan and the Galien River is the charming town of Union Pier. With Chicago only 75 miles away, Union Pier is a big draw from the hustle and bustle of urban living. The 400-foot stretch of soft white sand of Townline Road Beach is perfect for a serene day of swimming and sunning, with the Union Pier Marina and St. Joseph Lighthouse open for exploration. Even pets are welcome in designated areas. Union Pier offers a variety of restaurants, and don’t forget to go to Oinks Dutch Treat for something sweet in the summertime. Wine Enthusiasts frequent St. Julian Winery & Distillery for a wide array of local wines, ciders and spirits, and nearby New Buffalo is known for its summer concert series.

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