My travel companion and I had a hard enough time finding food and drink in Grand Marais. We couldn't locate this place called the Angry Trout because we'd been calling it so many different names (the Smiling Trout, the Grumpy Trout, the Happy Trout). Finally, we confused ourselves so much we were looking for the Smiling Trout. "That's not it," Elisha said. "That place starts with an 'A'." (The place was so dark we could barely see it from the road.) "Oh yeah," I said, "Where could it be?" We tried the GunFlint Trail and there was nowhere to sit despite a sign that said "Seat Yourself". So we went to a connected bar called the Raven, and the *** bartender slapped a drink menu on our table and never came back to get our order. Trust me, we do not look like amateurs who need to pick from the ***ing drink menu. She was just feet away at the bar with three patrons - locals, I assume. We were the only other people in the place, and the only ones without drinks. In short, we were being ignored. So after 20 minutes, we left. I would not recommend this place at all. In fact, I say boycott it.
We finally found a smiling face, great service, excellent food, and pretty darn good wine at My Sister's Place. If you find yourself in Grand Marais (which I wouldn't actually recommend you do, but just in case), go there. Our bartender gal was sweet as could be. She took our pictures with the silly red flannel shirts on, and she chatted with us and made us feel welcome despite being the only ones left at the place. I highly recommend My Sister's Place. Try the Juicy Lucy. It was fabulous!
Grand Marais's night activities really get started in the fall and last the winter (September -March). You see, that is the only time when 'night' comes early enough to include evening activites. There's the community theater, Friends of the Library meetings, school plays, school sports and concerts, and the annual Christmas 'Messiah' program at the Luthern Church. In the summer and winter, night is a time for families, around the campfire or sitting on the lake listening to the loons. If you run up to Grand Portage, there is the Casino.
A winter night activity is watching the sunset. Seldom is it a summer activity as the sun sets after 9:00 pm and so far to the northwest that dusk sets in from the Sawtooths for hours. But in winter, the sun will go down between 4:30 pm and 6:00 pm. It sets quickly over the Sawtooths Mountains, far to the south. So, if you're out on the harbor and it's a clear evening, you'll see the sky turn orange and red and streams of light coming off the water, before it ducks behind the hills down towards Duluth. Actually, it's a seldom seen event as the temperature may be hovering around -15F (-26c) or colder.
Seriously, most people come to these towns specifically to GET AWAY from throngs of loud drunken partygoers. However, if you want a pleasant conversation and a couple good beers with a nice meal, there are many worthwhile places to pick from. Sven and Ole's Pizza features an elevated bar with regional and unique beers. They are most known for their pizza. There are lots of others worth a visit as well, such as Gunflint Tavern, with its extensive menu and choice of fine microbrews. The tavern frequently features live music from regional artists as well. I was pleased to be present in May when the Duluth group TWO MANY BANJOS was playing. Blue Water Cafe has pleasant breakfasts, lunches, and dinners. It has been a long standing institution in Grand Marais. It is nicknamed "The Meeting Place," since a lot of regulars meet for coffee in the mornings. Angry Trout has some pretty adventurous seafood and fish entrees and features a gorgeous location right on the harbor. Harbor Light is just up the road and is an inviting supper club with a great variety.
Like most smaller cities up north, people visiting or living around Grand Marais tend to tire earlier and get up earlier for the gorgeous mornings. If you come here looking for tons of late-night techno clubs and raucous bars, you will not enjoy Grand Marais much. BUT, if you open your eyes to all of the natural beauty and the quiet charm of the town, you will find it very hard to leave. Most people choose Grand Marais BECAUSE it is clean, quiet and picturesque.