Crawfordsville is like a lot of small towns that aren't close to very much. It's very similar to Greencastle, 30 miles to the south, which I lived/worked in for a year (and made $15K doing it). There's not a lot to do in town, and there aren't a lot of 20-something single people to do anything with (other than the 20-something single people that you probably won't be going out of your way to hang around). The big annual event is the Ben Hur Festival (author Lew Wallace is from Crawfordsville), which is one of those shut-down-the-town-square and have a craft fair things. The other big event for the locals is the county fair, but that's pretty much par for the course in most Indiana counties.
There is competition -- there is another paper (called "The Paper") that circulates Montgomery County, founded when a few local merchants got upset with the J-R's cutbacks in coverage a few years back (at least that's what the story that's been told me is ... thirdhand from a former J-R staffer) and decided to put their money where their mouth is and bankroll a paper. Crawfordsville is one of the smallest towns in the country with competing dailies.
Purdue is 30 minutes away, and that's probably where you'll end up going for fun. There is an all-male D3 school in Wabash College (which is one of the top academic schools in the country ... just ask them). Indianapolis is a 45-minute drive away, and you should have opportunities to cover the Colts/Pacers/IMS events. Crawfordsville is far enough away from Indy that its readers see the J-R as their primary paper, so they want to read the pro stuff -- not just the HS coverage, so you should be able to cover those things if you want to. They used to cover IU and Purdue regularly, as well, but that's when they had a 3-person staff.
The cool thing is, you'll get to cover the single-best small-college event in the country -- the DePauw-Wabash Monon Bell football game. I've been to quite a few Big Ten games, but nothing matches the atmosphere and on-field intensity I've experienced at the Monon Bell game. Wabash is usually a pretty strong football program (bonus: alma mater of Pete Metzelaars, who was a starter on Wabash's national championship basketball team in the early 1980s).
In addition to Wabash, there are three high schools in the county, all mid-sized -- the town school (Crawfordsville HS, home of Indiana's first basketball state champions ... Crawfordsville is the home of the first basketball game ever played in Indiana), plus two consolidated county schools north & south of town. They have in the past provided some coverage of 4 or 5 fringe area schools outside the county, but I'm not sure they do that anymore. Crawfordsville HS won the Indiana 3A baseball title this year, and seems to be strong at both diamond sports. North Montgomery was a football power a decade or so ago, but other than that, they really don't stand out athletically.
For those with a mind to do some history enterprise stuff, there's some really cool opportunities. We're two years away from the 100th anniversary of Crawfordsville being the inaugural state champions in basketball. Wingate, which is a few miles up the road in the North Montgomery district, won back-to-back state titles in 1913-14 with an enrollment of less than 20 boys. One of them, Homer Stonebreaker, is considered the greatest of the early Indiana basketball players. They backed it up in 1919, when Wingate went to Chicago and won the national prep invitational (they & Crawfordsville both got suspended from the IHSAA that year over some recruiting spat, and faced each other in the finals of the national tournament instead).
