Your ticket to summer's grand finale in New Buffalo
On a bright, clear weekday in September, you may find yourself at a crossroads. Do you knock out ten more emails? Or do you sneak away to the shore for summer’s glorious last hurrah?
In Harbor Country, the answer is simple. It’s prime time to float. Beaches are wide open. Lake Michigan remains warm. And the vibes are mellow, wherever you roam. Because beyond the shore, you’re in the midst of peak abundance: ripe vineyards and orchards, lush hiking trails, well-curated shops refreshed for the season, and farm-to-table restaurants high on the harvest’s finest produce.
It’s a golden, remarkably chill moment. Restaurant reservations are optional. Late hotel checkouts, encouraged. All you need is wanderlust, some ideas to spark adventure (see below), and a day plus change to escape to New Buffalo.
Morning
Walk the Lake Michigan shore | New Buffalo
Nature brings the perfect gift to summer’s going-away party: average daytime highs in the 70s, on land and in Lake Michigan. On a serene September weekday, it’s an equilibrium best experienced in bare feet. New Buffalo Beach is especially magical at sunrise, with 16 miles of continuous coastline before you and barely a soul in sight. Walk the shore or, better yet, have a swim. Then climb the elevated walkway to dry off and catch picture-perfect lake views over the hilly dunes.
Get an Unskippable Breakfast | New Buffalo
When the outlook’s this beautiful, you could just spread a blanket on the sand and camp out. Or you may be enticed to explore. Either way, you’ll need breakfast. And around here, you have excellent options. A short walk from the beach, Brewsters comes through with marscapone-stuffed French toast, breakfast BLTs, and more day-off indulgences. A bubbly brunch cocktail in their sun-dappled courtyard is a more-than-acceptable way to change your status to ‘out of office.’
Window Shop | New Buffalo
If fall gets you in the mood for a home or closet refresh, Whittaker Street’s got the goods. Just around the corner from Brewsters, Michigan Mercantile’s collection of concept boutiques is an aspirational mix of housewares, books, and clothing. At Lakeside Goods, find European ceramics, linens, and artisanal accessories for table and home. Next door, Book Shore’s large-format art and lifestyle books are packed with inspiration for nesting and travel. And at Lake Feste, browse for under-the-radar French designers and stateside lines like Trovata.
Afternoon
Have a No-Pack Picnic | Union Pier & Three Oaks
Hop in the car and head north on Red Arrow Highway. You’ll pass the scenic Galien River County Park and be in quick stopping distance of Warren Woods primeval forest—unique natural landmarks with low-commitment hikes. After, how about a picnic without the prep? Enjoy gourmet sandwiches at Whistle Stop Grocery seated at charming outdoor tables. Or swing east to Journeyman Distillery. The award-winning distiller’s Staymaker restaurant is a draw for its historic factory building, Detroit-style pizza, and option to lunch outside by Welter’s Folly—one of the world’s largest putting greens. Play a round with cocktail in hand, if you’re feeling especially vacation-y.
Treasure Hunt | Red Arrow Highway
Red Arrow is dotted with superb vintage and antique shops, from New Buffalo north to Sawyer. With booth after booth of vintage furniture and décor, original art, clothes, and heirloom jewelry, Harbert Antique Mall is a multivendor mega-market for those who really enjoy the hunt. Operated by Rivich Auction House, they source from primo estate sales across the Midwest. Happen to be here on Friday? Pop into Sawyer’s Sojourn, a destination for fans of artisan-made ceramics and earthy housewares, and Harbert’s Alchemy Art & Antiques for eclectic vintage furniture and art sourced from some of the country’s top antique fleas.
Explore the Vineyards | Baroda & Buchanan
The official name is the Lake Michigan Shore American Viticultural Area (AVA), but you can also call it one of the Midwest’s most historically rich, plentiful wine regions. The AVA’s wine trail could be its own day trip through rolling vineyards and tasting rooms. But a one-estate visit is well worth a detour into the countryside. At Dablon Vineyards & Winery in Baroda, sip estate wines on a hilltop terrace with views of hand-planted vines. Nearby, get a two-for-one experience at sister vineyards Tabor Hill and Round Barn, on idyllic adjoining properties. Local tip: The estates share wooded walking trails, where to-go glasses are absolutely allowed.
Evening
Rest & Recharge | New Buffalo
As afternoon fades, The Living Room at Marina Grand Resort is a stylish, comfy spot to take a pause. From 3–5pm daily, the café-slash-lounge hosts a happy hour offering low-intervention, small-production wines, cocktails, beer, and a snackable cheese and charcuterie board. Sink into a sofa by the fire, or elevator up to one New Buffalo’s hidden treasures: the resort’s rooftop, with lounge-y seats and a fantastic view of the harbor and Lake Michigan. Before you head out, browse Stand Magazines‘ popup, a local seller with a New York newsstand-worthy collection of independent and hard-to-find pubs.
Dine Harborside | New Buffalo
The air is crisp and cool. The evening light sparkles. September is practically begging you to enjoy a slow dinner outdoors. Harbor Country’s al fresco dining options include lovely patios, decks, gardens, and yards. In New Buffalo, you’ll also find tables tucked into the peaceful marina. Treat yourself to elevated pub fare and somm-curated wines as you watch boats cruise into their slips at Bentwood Tavern. Or, at the other end of the harbor, set your sights on the lake at The Stray Dog’s 21+ rooftop serving guilty-pleasure bar and grill fare with a view of the sun as is sinks into the horizon.
Unwind with a Nightcap | New Buffalo
Not ready to call it a day? How about an after-dinner drink. It’s hard to miss Michigan’s new main street darling of coastal cool, PostBoy. The hotspot’s got a big, breezy patio and an eclectic lineup of amaros, sojus, sakes, sherries, and envelope-pushing cocktails. (Hypnotiq is a surprisingly well-played ingredient in the minty This Lil Daddy.) Before you say goodnight, there may be time for one last walk to the beach. It’s one of the dreamiest spots to watch the yellow-tinted moon rise.
