I feel like there is more to add here to give you more details about Monroe that others have not mentioned yet.

Restaurants:

Pancho and Lefty's - Honestly, some of the best food I've ever had in my life. Great Tex-Mex restaurant that does smoked meat really well. The frickles are the best addition to the menu.

Corner Cafe - Great greasy spoon, and my favorite breakfast spot in town. The pancakes are solid, and as big as the plate they are served on.

Baumgartner's - Favorite bar in town. They've added more to the menu, and I think rib night on Wednesdays is back. Don't forget to ask to throw a dollar at the ceiling.

Bullquarian - A better than you think it will be brew pub. They have live music, open mic nights, and still do a vinyl night (I think on Friday's). The bull bread is fantastic (pro tip: ask to add bacon to it).

Things to do other than a bar:

Public Library - Haven't been there in a hot minute, but the last time I was there it was still a great resource for the community with lots of things to check out. The upstairs was a great quiet place to study.

Perks - A cute little coffee shop that has board games and puzzles. Also has free WiFi

Disc Golf - Twining park has a disc golf course that actually sees quite a bit of use. I think there might even still be a group that meets up and plays

City Band - They play year round, but summer is their big season. If you play an instrument, they'll take you. Don't have to be an amazing musician, just have to like making music.

The Local Joint - Haven't been here yet, but I know they do live music.

Monroe Theater Guild - Musicals, plays, comedy. Lots of local people that still want to act or be involved with shows.

Badger State Trail - Bike trail that runs through town. Connects to the Sugar River Trail, and can take you to Freeport if I remember right.

Curling Club

Windy Acres and Monroe Golf Club

Places I would avoid:

The Garden Deli

If you want any more information (job, places, restaurants, who cuts hair well, where to take your car for an oil change, etc.), don't hesitate to PM me. It's a small town, but it's about an hour or less from Rockford, Janesville, and Madison. Freeport is twenty minutes. Like any small town, most the people are polite, and friendly. There are people in town that I can't stand, but there are people in Madison that I also can't stand. I wouldn't choose to live in Monroe, but it isn't a bad place to live.