Avalon Hill, 1977, 3-6 players, ages 10 and up. Rail Baron feels an awful lot like Monopoly to me (except without most of the boring tedium). Play takes place on a board featuring a map of the United States criss-crossed by several dozen rail routes (from the pre-merger days). Each player starts out in a city on the map and turns consist of rolling on a random destination table and then rolling dice to move your marker from your current location to your randomly determined destination. The tricky part is picking the rail routes for your journey that will wind up costing you the least amount of money to use (you pay $1000 per turn to use unowned rail routes or routes you personally control, and much more to use routes controlled by other players). Once you reach your destination you receive a cash payout from the bank commensurate with the distance of your trip (a short trip between two cities in the southeast might earn you $5000 or so whereas a long coast-to-coast journey could earn you $30,000 or more).
After each successfully completed trip and subsequent cash payout, players can then elect to purchase a rail route. These range in price from $4,000 for very small short lines up to $40,000 or more for huge routes that cover much of the country (UP, AT&SF, SP, etc). Purchasing railroads serves a dual purpose - since your turns are spent running around the country from city to city, you want to have as many safe (IE, cheap) ways to get around as you can manage. And similarly, you also want the other players to be spending all of their money using your rail routes instead of their own (allowing you to buy even more rail routes). You can also use your money to purchase an Express or a Super Chief (which allow you to move around a little faster). The ultimate goal is to amass $200,000 and then return to the city from which you started the game. At this point it gets a little silly - if another player lands on your token before you make it home, you have to pay them $50,000 and start over (not totally over, but start over earning money in an attempt to get back up to $200,000). If you manage to make it to your home city, money intact, you win.
The rules are clear and concise and take maybe 5 minutes to buzz through. The game is very simple to play and once you've played it, you'll rarely (if ever) need to re-reference the rules. So, how is this game like Monopoly? Well, apart from the fact that the money looks like Monopoly money and the railroad title cards look like Monopoly title cards, the actual mechanics of the game are very Monopoly-like. Instead of rolling dice to move around the board to "Go" and collecting $200, you're rolling the dice to move around the country to collect your multi-thousand dollar payout. And instead of trying to avoid landing on other players' properties and paying them rent, you're trying to avoid having to use other players' rail lines and paying them user fees. You can even get a literal monopoly by controlling all of the rail routes into a given destination city, so a player will have to pay through the nose if they roll it as a destination (having to pay you both on their way in and on their way out).
This game is actually quite entertaining, at least in the early stages when everyone is scrambling around buying up rail routes. Once everything gets bought up, it does tend to stagnate a bit (much like Monopoly as well). I guess the main complaint about this game is that it simply goes on too long, and I can certainly see where someone might think that. However, in our group we really don't have a problem declaring a winner without playing the game right down to the bitter end. The game is "last man standing" (IE, if you go broke, you're out of the game), so we'll either play until somebody gets wiped out or until things start to stagnate and then just count up everybody's money and holdings and declare a winner (again, just like you would in Monopoly).
So, overall this is a very solid and entertaining game that provides some decent intellectual challenge (plotting your routes through that spaghetti maze of criss-crossing rail lines can take a surprising amount of brow knitting). It feels very much like a classic to me, but as of this writing it is out of print (which I find quite surprising), and highly sought after by collectors (which I don't find surprising at all). I've seen copies sell on eBay for well over $100.