Southwest Michigan is the perfect destination for a fall weekend getaway from late September to early October! From quaint beach towns on Lake Michigan to scenic drives through vibrant foliage, there’s no shortage of things to explore.

If you’re looking for the perfect place to stay during your fall weekend getaway, Third Coast Vacations can be your home base as you explore the region’s charming small towns, local wineries, and fall festivals.

Our selection of warm and welcoming vacation rentals is perfect for creating unforgettable memories. Each property is designed to offer a relaxing retreat, the perfect place to unwind after a day of hiking scenic trails or strolling through charming small towns like New Buffalo and Union Pier.

This guide highlights the best fall weekend getaways in Southwest Michigan, including fall festivals, farm-fresh orchards, local wineries, and more. Let’s dive in!

Why Southwest Michigan Is Ideal for Fall Getaways

A group of friends enjoying a fall evening in a vineyard, toasting with glasses of wine. They are dressed in cozy autumn clothing, surrounded by golden-hued grapevines and soft sunlight. A wicker basket and a bottle of wine are on the table. | fall weekend getaways in sw michigan

Southwest Michigan shines in the fall with some of the state’s most stunning natural landscapes and small-town charm. Visitors can participate in an iconic fall color tour while they enjoy the crisp air and mild temperatures. This inviting atmosphere is the perfect backdrop for outdoor adventure. This region is known for its lively fall festivals, celebrating the season with local food, craft beverages, and family-friendly activities. Head north along the scenic highways, and you’ll encounter beautiful small towns and discover hidden gems like local art galleries that showcase regional talent.

Top Towns for Fall Weekend Getaways in SW Michigan

A scenic wetland area with a winding wooden boardwalk stretching over marshy water, covered in patches of green algae. The surrounding landscape features fall foliage with trees in shades of yellow, orange, and green under a clear blue sky.

New Buffalo, Michigan

New Buffalo is one of Southwest Michigan’s most popular fall weekend getaway spots. Located on the shores of Lake Michigan, this beach town has plenty of activities to keep visitors entertained. Enjoy walks along the beach, wine and beer tasting at nearby vineyards or craft breweries, and hiking trails that show off the best of Michigan.

Here are some great properties for your New Buffalo getaway:

  • Pinewood Cottage (Sleeps 6) – Cozy two-bedroom home featuring a backyard firepit, jacuzzi tub, and a kid-friendly play area, all within walking distance to the cafes, restaurants, and beachfront of downtown New Buffalo. 
  • Whittaker Suites (Sleeps 12) – Three beautifully renovated, coastal-themed suites feature fully equipped kitchens, king-sized beds, and amazing access to all downtown New Buffalo has to offer! 

Union Pier, Michigan

Union Pier is a quieter, more intimate destination for a cozy fall retreat, perfect for leisurely bicycle rides or peaceful walks along its scenic paths. Union Pier also focuses on farm-to-table dining, where you can enjoy fresh, local ingredients in cozy settings, like at Timothy’s Restaurant. 

Here are some great properties for your Union Pier getaway:

  • Pier Michigan (Sleeps 8) – Charming three-bedroom home featuring cozy lakeshore decor, a firepit, a hot tub, and easy access to downtown Union Pier’s shops, restaurants, and Townline Beach.
  • Pier Bliss (Sleeps 8) – Newly renovated three-bedroom home, offering easy access to local beaches, wineries, and shops, with family-friendly amenities like a lower-level hangout space, outdoor games, a screened porch, fire pit, and hot tub.

Lakeside, Michigan

Lakeside is a hidden gem known for its serene atmosphere and natural beauty. This town is great for a quiet escape, where visitors can enjoy long drives through tree-lined roads or explore nearby nature preserves. Warren Woods State Park is just a short drive away and has hiking trails through beech-maple forests.

Here are some great properties for your Lakeside getaway:

  • The Cornelia Cottage (Sleeps 6) – Fully renovated, three-bedroom lakeshore retreat just steps from Lake Michigan, offering charming coastal decor, a fully equipped kitchen, a screened porch, and a spacious outdoor area with a fire pit.
  • Modern Living at Lake Michigan (Sleeps 12) – Spacious, vacation home with beautiful architectural details and a guest house, situated across from a private neighborhood beach. With vaulted ceilings, a media room, screened porch, hot tub, and more, this home is a showstopper.

Sawyer, Michigan

Sawyer is home to Warren Dunes State Park, a popular spot for hiking and exploring sand dunes. After a day of outdoor adventure, visitors can unwind at one of the local craft breweries or visit a nearby orchard for fresh apples and pumpkins.

Here are some great properties for your Sawyer getaway:

  • Beach Daze (Sleeps 7) – Cozy, updated duplex home, just 1 mile from Warren Dunes State Park, with easy access to local restaurants, wineries, and breweries, with a large backyard, fire pit, and outdoor dining.
  • Casa Azul (Sleeps 10) – Beautifully decorated, family-friendly home located on a quiet wooded lot, featuring a spacious backyard, screened porch, hot tub, and a cozy bunk room for kids. Enjoy easy access to local beaches, antique shops, and restaurants.

Baroda, Michigan

Known for its rolling hills and vineyards, Baroda is a must-visit destination for wine lovers. The town is home to several wineries with fall wine tours and tastings, where visitors can sip on seasonal blends while taking in the beautiful countryside. Baroda also hosts fall events like wine festivals and farm activities and is a short drive from pumpkin patches and hayrides in nearby Three Oaks.

Here are some great properties for your Baroda getaway:

  • Vineyard Vista (Sleeps 8) – Luxurious wine country retreat with stunning country views and direct hiking trails to both Tabor Hill and Round Barn wineries! 
  • Blueberry Fields (Sleeps 15) – Charming five-bedroom home nestled in Southwest Michigan’s wine country, offering spacious living areas, a hot tub, a tiki bar, and outdoor dining, all within minutes of Warren Dunes State Park. 

Bridgman, Michigan

Bridgman is a charming town that blends small-town warmth with outdoor adventure. Home to Weko Beach, visitors can enjoy quiet walks along the Lake Michigan shoreline. Bridgman is also known for its craft beverage scene, with several local breweries serving seasonal fall beers perfect for sipping after a day of exploring.

Must-Do Fall Activities in Southwest Michigan

A person with a backpack walks along a peaceful hiking trail through a dense forest filled with vibrant yellow and green autumn foliage. The path is covered in fallen leaves, and the hiker is framed by tall trees as they explore the quiet, natural surroundings.

Fall Color Tours

Festivals and Events

  • St. Joseph Fall Fest (St. Joseph) — St. Joseph’s annual Fall Fest offers pumpkin decorating, hot air balloon rides, and a range of local food vendors, making it perfect for a family day out.
  • Four Flags Area Apple Festival (Niles) — This beloved event in Niles features apple-themed foods, carnival rides, and a charming small-town atmosphere.
  • Apple Cider Century Bike Tour (Three Oaks) — Cyclists won’t want to miss the Apple Cider Century Bike Tour in Three Oaks, which takes riders through Southwest Michigan’s scenic fall countryside and serves fresh apple cider and treats along the way.

Local Food and Drinks

Plan Your Perfect Fall Weekend Getaway in SW Michigan

From strolling down beautiful beaches in New Buffalo to exploring scenic trails in Sawyer, Southwest Michigan is a dream destination for a fall getaway. You’ll be surrounded by stunning landscapes, charming small towns, and activities that cater to every type of traveler.

When you’re ready to turn your fall vacation dreams into reality, The Third Coast Vacations team is here to help. Whether you’re looking for a quiet retreat in Union Pier or a beachside adventure in Lakeside, our curated selection of properties will exceed your expectations. Browse our vacation homes today and discover how easy it is to make Southwest Michigan your home away from home this fall!