Who says a vacation has to be sunshine and beaches? When you’re still on a college budget and pressed for time, sometimes you trade a spring break trip for a weekend road trip.

The best man from our wedding planned our little Michigan getaway for a couple of couples to get to know one another better. It also served as a nice break from our everyday routines. So best-man Jake, his new girlfriend Katie, and the Allens road tripped to New Buffalo, Michigan for company, wine, and antiquing.


The first step in any budget-friendly getaway is inexpensive lodging. The first place I suggest looking is AirBnB. We stayed in the coziest, private upstairs loft on our trip, not far from the downtown shops, the lake, or the wineries and breweries.

A chilly fall is technically the off season for a place like New Buffalo, right on Lake Michigan, but we favored it due to the smaller crowds. If you are the lake-type, visit in the summer. If you’re the shopping, drinking, and eating type, visit in the fall.

After finding our AirBnB nestled in the fall trees, we headed down the Wine Trail for some taste testing. Our first stop was the Round Barn Estate in Baroda. For just $12, we were given a souvenir wine glass and a punch card redeemable for six tastings of our choosing. Round Barn isn’t just a winery, it’s also a distillery and brewery. The punch card provided the option for generous tastings of any of the above. A drink for any palate, trust me.

Recommendation: Trading in two punches for a mixed drink –– like Round Barns own version of a White Russian.

Next on our trip down the Wine Trail was Tabor Hill. Round Barn provided a fantastic, casual environment, but no food. Which is why Tabor Hill is where you’ll want to stop if you’re looking for a bite to accompany your cocktails. We didn’t order food at Tabor Hill, but I promise they do have a great dining selection!

Recommendation: Don’t be afraid to step outside of your comfort zone. I’m not a big fan of extremely sweet wines, but Tabor Hill had great Cherry and Sparkling Cherry Moscato!

After socializing and winery hopping, the four amigos grabbed a bite to eat at The Stray Dog. Even during prime dinner time our table wait was well under an hour –– a perk of the “off” season. At a cozy table in front of a fireplace, we split the spin dip, and chips and guac. Great service, and even greater food, I would highly recommend this fun, laid back environment.

Recommendation: The spin dip, and their thick, juicy burgers!

The Stray Dog may have ended our night out, but it didn’t end the night in. Back at the AirBnB, we continued to socialize over homemade brownies, bananas, and sangria. Nothing screams “sleepover” quite like a few rounds of Heads Up!, The Game of Things, and Never Have I Ever.


Against the guys’ better judgment, we bounced around at the local shops and boutiques on the way out of town. Katie scored a handmade bracelet and some soap accessories, while I purchased a new doormat!

On the way out of town, we had to make a few pit stops at a few antique shops we passed on the way down the Wine Trail. The first one, Plum Tree, despite its whole-in-the-wall first impression, was the only location we made purchases at. I purchased two decorative vases, and Katie found some unique pieces for her mom.

Although we never made purchases, we explored the massive shop that was Lakeside Antiques. Lakeside has one building for high-end pieces, and another for general finds like basic furniture, decor, jewelry, etc. It was in the “low-end” building that I beat Jake in a game of Checkers, but I’ll sum up that experience with a just few photos…


Not within a comfortable driving distance to Michigan? Research wineries and local hideaways in your own region! You’re bound to find some place to sneak off to for a weekend. It may just be the refresher you didn’t know you needed…but you probably already knew you needed a break.

Have a weekend trip planned already? Or maybe you really enjoyed your last one? Share your trip itinerary with myself and other readers in the comments below, in my inbox, or on my most recent Instagram post!

Happy road tripping,

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