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The perfect weekend in New Buffalo, MI

When I realized I had a free weekend in September (and my mom agreed to take the kids) I got to planning a weekend in New Buffalo, MI right away. Sneaking away for a weekend isn’t something we get to do often, but when we do, we definitely like to make the most of it.

I searched Airbnb, VRBO, googled, asked Facebook and Instagram, and started making a list. My hunt for accommodations wasn‘t very promising. I love an eclectic Airbnb when traveling, but I wasn’t finding much of anything for our dates that made sense for just two people. A friend online suggested we stay at Four Winds and we thought that sounded like a fun change of pace so we booked it. (

We headed toward Southwest Michigan Friday afternoon. Although it’s less than an hour away, there is a change in time zone that eats an hour on your way up. We checked into our room at the Four Winds and were pleasantly surprised by the accommodations. I kind of anticipated everything smelling like an ashtray, but never once detected a smokey smell. We had a few hours to spare before our dinner reservations so we headed to the pool for a drink and a snack. The outdoor pool/hot tub was definitely a nice feature that sets this hotel apart. There is lots of outdoor seating, live music on the weekends, and no shortage of cocktails or food. We ordered the pretzel sticks and they hit the spot.

After about an hour, I headed up to the room to get ready for dinner. We went to the Terrace Room, a waterfront Italian restaurant. ( Although I have been to New Buffalo many times this was a restaurant I had never dined at before. I am going to include some outfit details since I usually get asked anyways and when applicable, I’ll throw in the shopping links.

dress: Ross

kimono: Amazon

booties: Free People

The meal did not disappoint. We started with a bruschetta trio and the fish dish. I’ll be honest, I was expecting something a little different from the dish featuring muscles, scallops, octopus, calamari, oysters, salmon, and one other that’s escaping me, but when in Rome (or in this case when dining at an Italian restaurant.) We also ordered a bottle of the Super Tuscan red blend and we shared the 16oz bone in rib-eye. I think I’ve had dreams about that hunk of meat. I would definitely return to this restaurant. Next time, I’ll skip the fish and reserve a seat on the deck for a different ambiance.

To conclude night one, we headed back to the hotel for a cocktail by the pool while the Crawpuppies jammed away. Before heading back to the room for the night, we tried our hand at gambling. I am not a gambler. I really detest losing money. I would rather spend it on concert tickets or literally anything other than gambling, but when you’re sleeping at a casino it’s kind of a rite of passage. I started with $40 and went to sleep with a $35 voucher so I did okay (don’t worry, I lost it all the second night.) My husband, on the other hand, had slightly better luck than me with Roulette.

Day 2 started off with sleeping in until 9am. It was glorious. Technically 8am Indiana time, but still really good sleep. We weren’t in any sort of a rush to get anywhere fast this day, so we just took our sweet time heading out to breakfast. New Buffalo has a serious shortage of good breakfast/brunch spots. I googled for awhile and didn’t find much, so we took a chance and ended up at a spot downtown. I think it was called Jackie’s cafe. I had the most mediocre eggs benedict for $13.50 and a bad cup of coffee for $3. Will not return. We headed straight from breakfast to the main drag of downtown and stopped into the new Starbucks. My current favorite drink is the apple crisp macchiato, made upside down, with a drizzle of carmel. It did not disappoint.

After about an hour of wandering the small shops of downtown New Buffalo and a quick trip to the lakefront, we headed back to the hotel for more pool time. Although my phone said it was 77° it certainly felt like it was in the 80s, the perfect last weekend of summer. We laid out, dipped our toes in the pool, and soaked in the hottub. This area was our favorite amenity of the hotel.

I had this amazing idea to get Redamaks carry out to eat while getting ready for our wine tasting adventures, but sadly, they were not doing carry out at that time. Instead, we stopped in for a quick burger on our way to Round Barn. Redamak’s is a New Buffalo legend. I don’t care if you don’t like burgers, YOU MUST EAT HERE when you visit. Thankfully, we had no wait time to be seated and very prompt service. A burger before a day of drinking is always a good idea. (

When planning our trip, we couldn’t find any wine tours for 2, so we just headed to Round Barn estate where we knew there would be entertainment to pair with the drinks. (

I had the Vodka Lemonade Frozé with the blueberry wine topper and it was heaven in a cup. (Sidenote: all straws I was served in New Buffalo were marine biodegradable and I have to give them some applause for that!) There was a great cover band that I didn’t catch the name of, but they did a fantastic rendition of Kings of Leon so they had me reeled in.

Before leaving Round Barn, we hit the gift shop for a bottle of wine for home and I ended up with Concord grape. I can’t wait to try it!

We left Round Barn and headed back downtown for some pre-dinner cocktails at the Hummingbird Lounge. It was seriously so cute, a little house converted into a cocktail lounge with a rather impressive menu. My husband has the smoked pineapple margarita and I tried the blueberry bramble. We ordered the eloté corn dip because we were ready for some food and still a few hours out from dinner. It was delish! Definitely stop in for a drink or two on your next trip. (

Our last dinner for the weekend was at Timothy’s. A little off the beaten bath in Union Pier, but absolutely worth a visit. We had the bang bang shrimp appetizer, Ahi tuna, macadamia nut and coconut encrusted grouper, and the key lime cheesecake. We ordered a bottle of Pinot Grigio and it was the perfect complement to the meal. In full transparency, the center of my grouper was uncooked. I’m not sure how this happened as the rest was delicious and perfectly cooked. I left the raw part on my plate and when the server came to collect our dishes he acknowledged it and said he was taking this off our bill. I never asked for him to remove it, but since about 1/3 of the filet was inedible I was grateful for the gesture. In spite of this little mishap, I still highly recommend and will absolutely be back. The key lime cheesecake was the highlight of our whole trip. When planning your next Southwest Michigan trip, do not overlook this spot. (

After dinner, we headed back to the casino to try our luck again. No luck was had. Not by me at least. We did run into some friends from home who were out celebrating their first night out as new parents so that was a fun little surprise for our trip. We went to bed and slept in until 9am again. I squeezed every last minute out of this hotel room and didn’t check out until 11am. For one final New Buffalo hurrah, we had lunch at Brewsters on the patio. I ordered the fig and prosciutto flatbread and my husband had the Cobb salad. (

It was the perfect way to wrap up the weekend and 45 minutes after departing the restaurant, we were home.

I hope you enjoyed this weekend recap, and look forward to hearing about some of your favorite New Buffalo spots that we may have missed. Feel free to share your favorite spots in the comments and let me know if you’re planning a Southwest Michigan visit soon!

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