View of homes and Boats on Inlet in Southwest Michigan

4 Reasons to Plan a Trip To Southwest Michigan

Published: August 16, 2024

Looking for quick getaways from Chicago? Southwest Michigan offers the perfect escape year-round, boasting rich fall colors, cozy winter landscapes, and summer lake activities. The region’s small-town charm and unique attractions make it a hidden gem of the Midwest.

Whether you’re a wine lover or an antique enthusiast, we’re rounding up the top reasons to visit Southwest Michigan and the most beautiful Lake Michigan vacation rentals.

1. Wonderful Wines

Rows of Grapevines in Southwest Michigan

When you think of wine-growing regions, Michigan likely isn't the first place that comes to mind. However, the state's unique geography makes it the perfect location to grow a variety of grapes, including Niagara and Concord. Since Southwest Michigan is on the southern end of Lake Michigan, the area experiences something known as the lake effect, causing moderate temperatures that don't hit extreme lows or highs. This temperate climate creates the perfect grape-growing conditions.

Michigan is quickly gaining recognition for its world-class wines and we highly recommend exploring the Lake Michigan Shore Wine Trail on your visit. The Wine Trail features a collection of twenty-one wineries and vineyards spanning Southwest Michigan. Outlined below are two of our favorite local wineries.

Tabor Hill Winery

Location: Buchanan
Distance From Chicago: 1hr 34 min
Sip and stroll at Tabor Hill Winery, where visitors can explore over 3.5 miles of vineyard and woodland trails while enjoying a glass of wine. If you’d rather sit back and relax, the winery also offers covered seating areas with views of the vineyards. Stop by Sunday afternoons for live music from Memorial Day weekend through the end of September.

Lemon Creek Winery

Location: Berrien Springs
Distance From Chicago: 1hr 37 min
Experience a legacy that spans 165 years at Lemon Creek Winery. Lemon Creek offers a diverse portfolio of wines, including dry reds, dry champagnes, orange wines, dry whites, and dry rosés. If you're bringing along kiddos, we recommend visiting during the U-pick season when guests can harvest their own fruit. Families enjoy picking cherries and peaches in the summer and apples and grapes in the fall.

2. Incredible Dining

View of Restaurant table near Boat Marina in Southwest Michigan

Thanks to a combination of local talent and skilled Chicago expats, the Southwest Michigan food scene is booming with incredible eats. Since the area offers an abundance of fresh produce and farm-raised meats, many restaurants cook with local ingredients sourced from the farms and fields around them. We think you'll enjoy the following local favorites.

Terrace Room

Location: New Buffalo
Distance From Chicago: 1 hr 26 min
Terrace Room offers an authentic taste of Italy right on the shores of Lake Michigan. This waterfront restaurant is known for its rustic Italian fare, featuring simple, fresh dishes made from scratch. Enjoy your meal on the patio with stunning lake views in the warmer months. As the weather cools, the cozy fireside dining inside provides a romantic setting to savor a comforting meal while still enjoying the scenic lake views.

Susan’s

Location: Sawyer
Distance From Chicago: 1 hr 15 min

Located in the historic Flynn Theater building in downtown Sawyer, Susan's Sawyer combines Chicago city vibes with the charm of Southwest Michigan. The cozy ambiance invites diners to enjoy an elevated yet approachable menu. Each dish is crafted with the finest local and imported ingredients, reflecting both the seasons and Chef Mike's creative inspirations.

3. Antiquing Opportunities

Vintage Green Antique Sign

Skip the touristy souvenir shops and bring back something truly unique by exploring local antique stores. Mixing modern and antique items is a design tactic used by some of the world’s top interior designers. Not only does it provide visual interest in your home, but it also allows you to showcase treasures from your favorite trips. We think you’ll love the following Michigan antique stores.

Trilogy Antiques & Designs

Location: Three Oaks
Distance From Chicago: 1 hr 22 min
Trilogy Antiques & Designs features a select group of art and antique dealers who share distinctively great taste. This curated experience almost feels like stepping into a beautiful art gallery full of unique items instead of a traditional antique store.

Antiques on the Bluff

Location: St. Joseph
Distance From Chicago: 1 hr 39 min
Antiques on the Bluff is a premier antique show at Lake Bluff Park in St. Joseph. It features over 50 vendors and runs on the first Sunday of each month from May through October.

4. Lake Michigan Excursions

Sailboat on Lake Michigan

Looking for a beach vacation without the blistering heat? Southwest Michigan is home to one of the largest freshwater seas in the world, Lake Michigan. Summer temperatures rarely exceed 80°F, making it an ideal spot for a classic beach vacation without the intense heat typically associated with summer trips. If you're planning a Michigan getaway, you likely have a few beaches on your list already. To fully enjoy the lake, consider booking one of these memorable water-based activities.

New Buffalo Sailing Excursions

Location: New Buffalo
Distance From Chicago: 1 hr 18 min
Set sail on Lake Michigan with New Buffalo Sailing Excursions. This personal sailboat cruise offers shoreline views you can't experience from land. While New Buffalo Sailing Excursions doesn't serve alcohol, they encourage guests to bring their own beverage if they'd like. We suggest grabbing a bottle of local wine to enjoy during your experience.

Lake Life Watersports

Location: St. Joseph
Distance From Chicago: 1 hr 45 min
Interested in creating an experience the entire family will enjoy? Check out Lake Life Watersports. This company offers waverunner and pontoon rentals, providing everything you need for a fun-filled day on the water.

Best Places to Stay in Southwest Michigan

Southwest Michigan Vacation Rental Backyard with Hottub and lights

The 100 Collection™ is proud to partner with Juniper Holiday + Home for the best Southwest Michigan Vacation Rentals. Owner Valerie Gangas created a collection of rentals that offer the best places to stay on Lake Michigan. Guests can expect richly designed living spaces, serene outdoor oases, and picturesque lake, forest, or blufftop views. Each unique space holds at least four people, making these homes great family options.

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