HARBOR COUNTRY DREAMING

Lake Forest native Ben Holland shares the latest from his chic New Buffalo restaurant, PostBoy, along with a few of his favorite things from his hometown.

Lake Forest native Ben Holland has been straddling the state lines of Illinois and Michigan most of his life, with a soft spot for his family’s beloved Harbor Country escape in New Buffalo. Both communities played integral roles in his personal and professional journey, then and now. He says friends from Everett Elementary School remain some of the closest in his life with celebrations of birthdays and other special occasions continuing to this day. In fact, he met his wife Claire at a Lake Forest house party shortly after graduating from Southern Methodist University. The couple got married on a beach in New Buffalo, which is where his passion for hospitality and a decades-long dream of opening a downtown restaurant in the area has finally come to life. Holland introduced PostBoy with up-and-coming culinary talent James Galbraith in November 2024 and it is quickly becoming one of the popular resort town’s hottest dining destinations. Outside of his recent foray into the restaurant world, Holland is also the founder and managing partner of his Chicago-based investment firm, First Principles Group, and lives in Lincoln Park with his wife and twin daughters. He racks up plenty of road trip miles traveling to New Buffalo and back, and he loves to visit his family in the Lake Forest/Lake Bluff area, especially when he can catch some local live music from his friend Brett Kreiner’s band, Kasekrainer. If you’re looking for Holland and his family this summer, they’ll be at their New Buffalo home base in dig designed by none other than Lake Bluff native (and recent Forest & Bluff cover girl) Maggie Getz.

Dream car? 1971 Scout 800B soft top in Brittany Blue. It’s one of my dream restoration projects—hoping to get to it soon! Favorite thing about working and spending extended time in New Buffalo? It feels like a world away. Catching the sunset over the lake every night is pure magic, and walking through the dunes melts the stress away. Most underrated Midwest dish or food item? I’m a simple man—I love deep dish. In Lake Forest, Ferentino’s is my go-to. In the city, Giordano’s and Pequod’s both hold a special place in my heart. Favorite restaurant in Lake Forest/Lake Bluff? Sushi Kushi Toyo. It’s a nostalgic spot from back in the day. Your cocktail of choice? The Last Word. Simple, delicious, and easy to make. Four equal parts: gin, lime juice, Luxardo maraschino liqueur, and green Chartreuse. A classic. Favorite thing about being a father? Raising two wild, independent, strong, confident girls who are ready to shake up the world. TV show or series you can’t stop binging? White Lotus has been a favorite, but I’m also into The Pitt right now. I once wanted to be a doctor, but an internship in Cook County Trauma changed that path. Major respect for health care workers. Favorite driving music? I make a yearly Spotify playlist called Girl Dad Jams and share it with friends and family. It’s a mix—from Big Wild to Charley Crockett to a bunch of songs I Shazam and save without knowing the artist. Lake Forest’s secret gem? Elawa Farms hosts Outstanding in the Field dinners every year—love those. This year, PostBoy and Chef James are partnering for the OITF Michigan dinner in August at Seedling Farm. Very cool to be part of it. Favorite Midwest escape? New Buffalo—hands down. It’s my happy place, and I still think it has so much untapped potential. I want to be part of bringing more fun to the area. Three people, dead or alive, you’d invite to dinner at your restaurant? My grandfather Verle—lost him in college and would love to share my life with him. Benjamin Franklin—my namesake, a brilliant inventor and thinker. And Gwynne Shotwell—President of SpaceX. I’d love to talk rockets, the future, and becoming multiplanetary. Favorite snack? Puppy Chow. My friend Coco Kellman used to make it when we were growing up—so good. Now I’m craving it. Next stamp on your passport? Our 10-year anniversary is coming up, so we’re debating between Chile/Argentina or something exotic like French Polynesia. Time flies—it feels like we just got married yesterday. Place in Lake Forest you always visit when you come home? My sister’s house in Lake Bluff. I love hanging with my nieces and nephew. It’s always a little wild and always a blast. Best city in the world? I love trying new places, so this one’s tough. But for a guy who’s into fun restaurants, beaches, scuba diving, ATVing, and sunsets, I’d say Saint Barthélemy.