I always research chowhound before I travel, so thought I'd contribute a little to the board. Vacation season is starting soon so some people might find this of interest.
I live in Chicago and have had a second home around New Buffalo for five years. My wife and I go out to eat a lot, so we're very familiar with the restaurants. You can eat very well in Harbor Country. Most of the people who come here are from Chicago so it's a pretty tough to please crowd, keeps the restaurants on their toes.
Moxie's used to be Jenny's Restaurant. Sadly, it's seemed to really have gone downhill in the past 6 months or so. The parking lot is almost vacant on weekends lately, not a good sign.
Miller's has closed for good.
Timothy's: the last man standing for fine dining. Lot of people like it, I think it's just ok. Cooking is too busy, overseasoned and too many things going on at once with a dish. Just ate there recently, and Timothy seemed to have fallen in love with wasabi - overpowered the crabcakes and a few other dishes. I would stick to the appetizers, main courses get too fussy and don't work as well.
Lot's of good options here.
Red Arrow Roadhouse: has also been written up elsewhere on this board. Great place, great atmosphere, price is right. Ribs are excellent, as is the broasted chicken. The Mexican dishes are always worth a try, they may sound weird on the menu but the end result is always good. Save room for dessert, especially anything with fruit.
Casey's: downtown New Buffalo. Really good ribs and steaks. Menu gets a little ambitious and some things fail, best off sticking to the basics. Fun place, loud and lots of drinking.
Heston Bar: off the beaten path some, a bit of a drive into the woods east of of Exit 1 of I94 and is actually in dreaded Hoosier country on the MI/IN border (County Road 1000N & Fail Road). Just go east on LaPorte Road east of 94 for a mile or two and then make a left at the road by the sign for "Heston Steam Museum" (1000N). Then drive down 1000N about 5 miles till you hit the restaurant, there's nothing in between but fields and woods. But the trip is worth it, a pretty drive. Your basic old-school kind of steakhouse. Good martini's, complimentary cheese dip like a Win Schuler's with the bread basket. Oysters and shrimp are good starters, and I'd stick to the basics like steaks and chops on the menu. Make sure you get the soups with your main course, homemade and always tasty. It's been around forever, lots of locals - good value, good food.
Grand Mere Inn: also off the beaten path, this is north a little ways in Stevensville, on Red Arrow Highway by Grand Mere State Park. They don't advertise, but easy to find. Just drive north on Red Arrow, it's maybe 3-5 miles past the Cook Nuclear Plant on the left hand (west/lake side) of the road. Similar menu to Heston's, a little classier atmosphere. Doesn't look like much from the outside but inside its linen table cloths and nappery, great views in the summer time. One of the few places in the area where you can see the lake (restaurant is on a bluff and lake is about a mile distant). Smoking section is by the bar, fun and rowdy. Non-smoking section has the views of the lake. Oh yeah, and the food is great. Best deal in the area, you can have a martini, glass of wine, appetizer and a decent steak and walk out of there for under $40 a person.
Union House: this just opened, on Red Arrow and Union Pier Road. I haven't been there, but my wife went last week and liked it a lot. Most of the menus in Harbor Country are pretty similar, most diners don't want a lot of adventure when they eat around here. She liked the crab cakes, and she was just raving about the medallions of beef with blue cheese. I think the chef has worked in New Orleans too, so anything creole on the menu is probably really good.
Redamak's: it's a zoo in the summertime, tons of kids. But they get you in and get you out fast, and the cheeseburgers are awesome. Old school, a thin patty with pickle slices, onion, mustard and ketchup. Crinkle cut fries. Everything on the menu is fried or deep-fried, don't come here if you're on a diet and stick to the cheeseburgers.
Smokin' Woodies: in Sawyer to the north, on Red Arrow about half a mile north of the light at Sawyer Road. Good ribs and pulled pork, great side dishes. The meat is hit or miss, depending on how much Woodie has been drinking that day. Might be charred, might be perfect - but the owner's a character and it's cheap.
Rio's: an unassuming little taco stand on Highway 12/Red Arrow south of downtown New Buffalo. It'll be about a half mile south of the traffic light of downtown New Buffalo, on the east side (away from the lake) of the road. Great tacos, homemade salsa, really good guacomole, and beans and rice. Lines get really long in the summer, but it's worth the wait. Get if for carryout, or eat it at picnic tables in the parking lot.
Lone Radish: on Red Arrow Highway, just north of Union Pier Road on the lake side of Red Arrow. Creative sandwiches, good quality ingredients. Tiny place and cramped kitchen, takes them forever to prepare the orders so be patient. Food is worth it, great sandwiches and good soups.