Check out the Italian sub at the Big Bear Deli on main street in Gaylord. Ask for it grilled.
A memorable sandwich with Boar's Head meats. The coffee is great, too.
Also, the Sunday morning brunch is outstanding at Paul's Pub in Johannesburg, 11 miles east of Gaylord on M-32. A nice buffet with waffles and omelettes made to order. And the waffles! Light as air and so tasty. I was a bit skeptical of my husband's waffle/hot syrup/whipped cream concoction until I took a bite.
For a dependably good burger in the Gaylord area try the Stampede Saloon on 27 South. I was told they get their ground beef from the family-run butcher shop down the street. The steak fries are great. So are the baked beans.
Rosco had a wonderful place called the 5th Street Grill but it closed when the chef left for Forest Dunes Golf Course just NE of Roscommon. Forest Dunes has a web site www.forestdunesgolf.com . Grayling has an old time bar restaurant called Spikes that specializes in Spikeburgers which are really quite good. There's a deli specialty store in Grayling called the Bloomin Grape that's worth checking out. 9 miles due east of Grayling is Gates Au Sable Lodge which has a very good dining room. Gaylord has every kind of fast food you can name and one or two "chowish" places. One is Diana's Delights on the main drag. Great breakfasts and lunches. They also do good fish specialties on Friday nites.
I'm not familiar with places in those towns, and hopefully others will chime in with recommendations. Here are some places worth considering that are not all that far away.
If you're looking for a splurge meal during your stay, there are two outstanding restaurants in Ellsworth, 28 miles west of Gaylord on MI-32. Tapawingo is considered by many to be the best restaurant in the entire state of Michigan, and it is absolutely wonderful. Rowe Inn is also in Ellsworth and it is another chow-worthy fine dining restaurant. If you can, try to incorporate either (or both!) into your stay. You'll find more info on their websites at www.tapawingo.net and www.roweinn.com
Also, Traverse City is about 50 miles west of Grayling, and you'll find recommendations of restaurants there in the recent discussion at www.chowhound.com/topics/413360 If you enjoy wine-tasting and hopping among wineries, the Traverse City area, including the nearby Leelenau Peninsula and Old Mission Peninsula, are known for their wide variety of excellent wines. You'll find descriptions of the wineries in this area at www.michiganwines.com/Wineries/wineries.html
One other source of information is the State of Michigan Tourism website, which has listings of restaurants (and other attractions) statewide, and you can use it to find a description, for example, of each of the restaurants by town (including 3 in Roscommon, 6 in Grayling, and 22 in Gaylord), at www.michigan.org/travel/dining/?m=7 (Click on the name of the town to find its web page, then click on Dining.) Granted, this isn't as good as first-hand experience, and again, hopefully others will provide recommendations, but in case they don't, it's better than nothing.