Southwest, Michigan: Where to eat, sleep and play

All of our favorites to eat, sleep and play in Southwest, Michigan. Including Union Pier, New Buffalo, and Three Oaks.

I have been visiting New Buffalo, Michigan since I was a little girl. In fact, my parents even had their joint bachelor and bachelorette party there over 30 years ago. I grew up going to the beach and going to the farmer’s market every summer. For our very first family vacation with our 4 month old, it seemed only right to head to Michigan. We rented a house on the beach and really had a vacation I’ll never forget. Ever had one of those?

Our family vacation to Southwest Michigan
Our family vacation to Southwest Michigan
Our family vacation to Southwest Michigan
vacation in southwest michigan


Just being 90 minutes outside the city, it is easy for a day trip and a weekend getaway. You can also take the Amtrak, but we learned there are very limited times from Chicago.

The entire Southwest Michigan has so much to do, there is a little something for everyone. The public beach with kayak and paddle boat rentals, make a stop at the Indiana Dunes, visit Four Winds Casino and various wineries, breweries and distilleries.

We would take Noah in this rocker and he would fall asleep right on the beach. Although he’s older now, at the time, this was a great way to keep him out of the sand and comfortable enough to fall asleep.

We also used this carrier the most for us to walk around the beach or town. I found it the most supportive one. Fabric carriers don’t seem to have enough support for my back.  We would strap him and go! The days of having a little one….:)

There are so many places to check out, but I listed some of our favorite spots and wineries we visit often.

Where to Eat

The Stray Dog- Serving great food and drinks, this is a perfect place to people or boat watch on their rooftop (21 and over). You can sit and watch the boats come in and out of the harbor. They have been open for more than 15 years and have become a New Buffalo staple with tourists and locals. (Noah’s asleep in the carrier if you look closely enough).

You also cannot have children sit at the bar, it’s a Michigan law we found out.

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Nani’s Cafe- This cute cafe is located in Union Pier and might possibly have the best muffin I have ever had. They serve fresh baked pastries and serve La Colombe Coffee. They also serve egg sandwiches in a buttered New England style roll. It is definitely a must stop along your drive on the famous Red Arrow Highway.


David’s Deli and Coffee– This cute cafe is located right in town and serves breakfast and lunch. They are most known for their reubens, but I had a bagel and cream cheese that I would get again in a heartbeat.

Oink’s Dutch Treat- Such a cute ice cream spot that’s been around for years, it’s a cute old school ice cream parlor. Plus it’s damn good!

Brewster’s Italian Cafe– Not only is the food good (the pizzas are awesome), the outdoor patio is the best feature. After a long day in the sun, you can grab drinks and food outside in what seems like someone’s home garden. They do not take reservations, but you can call ahead of time and get your name on the waitlist, which on a nice night, there almost always is one.

Redamaks– Kind of a legendary burger spot.

Where to Play

New Buffalo Beach and Warren Dunes- New Buffalo Beach just recently got a makeover with a cute concession stand and upgrade playground. It fills up quickly, so get there early.

Journeyman Distillery – Located in Three Oaks, Michigan and the area has lots of cute coffee and antique shops, and of course, the famous Journeyman. Although I don’t drink bourbon, I fell in love with this place. The space is gorgeous and often used for wedding and events, even being featured on wedding sites like The Knot.

We took a tour that ended with 16 tastings (I was the DD) and had an awesome time. After the tasting, you can sit at the bar for crafted cocktails or their delicious locally sourced burger. Definitely worth the 20 minute drive from New Buffalo to check this place out. Luckily, Noah slept the entire time in the carrier, but if he was older, I don’t think we would be able to do the tour. Although, the restaurant is family friendly!

Three Oaks has some really cute shops and a lot of art shops you can stroll up and down the main street.

Dablon Winery– Dablon opened in 2015 and we have fallen in love with their wine and tasting room ever since. We discovered it while doing our normal stops along with Wine Trail. To our surprise, it turned out to be the same owners of the Music Box Theater on Southport! Even their Matinee Red wine label is a photo of the theater. They do tours on Fridays at 2 pm and often have live music. I can’t tell how nice it is to sit outside, overlooking rolling vineyards, while drinking delicious wine. I highly recommend their Chardonnay (FYI..I am not even a Chardonnay drinker). It is very buttery!

Wine at Dablon Winery

Recently, they are now serving their wine at Gallagher Way (Former Park at Wrigley) or you can stop in at the Music Box for a glass of wine and a film.

Gravity Winery- Another stop along the Wine Trail is Gravity Wine. This winery sits on top of a hill overlooking water and so much greenery.

View at Gravity Winery
Winery at Gravity Wine

Dress: Fab’rik in Wicker Park

The best part of this winery is their flight pairings. You select any four tastings of wine, and then it is paired with yummy samples like cheese, crackers and chocolate.  Although these wines tend to be sweeter, this is another place you could sit and relax with wine overlooking a beautiful view.

I would also highly recommend taking a wine tour Grape and Grain Tours or Fruitful Vine Tours. I did with some friends for a birthday party and it was so much fun! But definitely not family friendly, over 21 years old is mandatory.

Where to Stay

We have stayed at several locations as a family, but also as a couple. There are lot’s of options. If you are planning on taking a winery tour, many of them pick up directly from the hotels.

Holiday Inn

Fairfield Inn Marriott- We have probably stayed here the most!

Air BNB– We stayed in this house with Noah for our first family vacation in Union Pier and it was perfect. It’s located right across the beach and walkable to Nani’s Cafe and a convenient store.

Marina Grand Resort– I have stayed here with friends and with Manny, both amazing experiences. The hotel is right on the harbor, you can watch the boats come in and out. It’s modern and a few blocks from the center of New Buffalo.

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Until next time,


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