Housing
As others have said in previous topics, you want to stay as close to the Stampede grounds as possible. The best places to stay in my opinion are downtown and the area around 17 Ave. SW called "Uptown". It's best to book this stuff a few months before, as the rates go up quite a bit for the week. I didn't spend more than $175 per night for my place, and there are certainly many options on AirBnB. You don't want to be too far west and have to depend on public transportation.
Transportation
Getting to Calgary isn't so bad if you're from the western US/Canada, since there are often direct flights to Calgary from some city in the region. Going from anywhere else requires some layover, and the most common one for an easterner would be Toronto since that airport has a lot of flights to Calgary every day.
Calgary airport is quite a bit north of the city center and one could drive there in about 10 minutes. There's a limited-stop bus from the airport (300) that will take you to the Calgary Tower downtown for $8.50. If you stayed outside of downtown, you'd probably have to take another bus though. One could also pay $50 for a cab, although I don't know where that would bring you.
Calgary public transportation is decent, but not great. There are several buses that go around the city, but they run every 15 minutes on peak periods, and stop running after 2:30 AM or so every day. The LRT trains run through downtown and by the Stampede grounds, as well as going to other parts of the city, but you'll probably have to find somewhere to even get to a station. The fare system is annoying at $3 ride with a system of paper transfers and tickets. Unfortunately, there's no weekly unlimited ticket, which I didn't like very much.
It wouldn't hurt to rent a vehicle, and this is especially helpful if you plan to hit up nearby parks or even Edmonton.
Food
There are plenty of dining options on 17 Ave. SW as well as 4 St. SW, not counting downtown. One can definitely expect to spend just under $10 on just food from a smaller establishment. The malls along Stephen Ave. (8 Ave. SW) have food courts and there are plenty of places along that strip itself. If you like burgers, you'll have a field day in Calgary since Alberta is known for its beef. I never went to any high-end places for dining, but in a city like this, I'm sure there's no shortage of them.
Safety
I found downtown and uptown pretty safe at night. There are enough areas where it was pretty damn silent, though. Definitely be a little attention at least.
One thing that also happens just about every night is the appearance of these random people playing music on the street. This is typically along 17 Ave. or near the Victoria Stampede station.
Stampede specifics
Your main points of interests during the week will be the grounds and outside establishments. The grounds are set up with a carnival as well as an 18+ tent known as "Nashville North". On weekends, lineups for this and other places start in the day, and on weekdays, expect to see people in the evening (think 5 or 6 PM). Entry to the grounds was $16 this year, and covers typically range from $20-40 anywhere else. Drinks average about $7.50 or so, and many people either pregame or sneak a bottle of some alcoholic drink for the lines. The airport has some duty-free shops, and it worked well for me. Figure out how much you're actually going to drink that week.
Another popular thing that people do is bar crawls. You essentially meet at a place, chill for a bit, and then go with other random people on a bus to three other establishments. They last about 6 hours and the two most common ones I saw were "Bust Loose" and "Student Tours". I did the former and didn't find it too bad. You can easily ditch the bus at any point on the tour and essentially get free entry to a location, which may not be a bad idea if you want to isolate a girl or leave a group with thin prospects. I found the tours to be nice, but nothing overly crazy.
One thing I would highly recommend is having a solid ID. Being one of the few American easterners in Calgary, many of the bouncers didn't trust my state ID, and I had to use my passport. I wouldn't recommend carrying around a passport, so be sure to have something that's a powerful identifier. The drinking age in Alberta is 18.
Locations
These are the places in went to at least once during Stampede.
Cowboy's
Probably the most popular place during the whole week. The actual complex is part of a casino in which there is a club (which is not bad itself); but the main party will be inside the tent that exists only during the week. The area is huge with multiple points for drink purchase and even food. The best talent I saw was here, but there's also a bit of a mean vibe here as this place gets a lot of out-of-towners and people with a bit of a mean streak. In my two times in the tent, I saw multiple fights as well as cops and security rushing to spots on one occasion. This place does bring in 50 Cent every year apparently, and Snoop Dogg also had a concert that I didn't go to.
Ranchman's
This is a bar that is located a good way south of downtown Calgary, but is reachable by the LRT train. It's got multiple bar spots and a respectable dance floor. I actually liked this place a lot since it had a good crowd, some talent, and was actually pretty fun. The main downside of this place is that it's far, and if you stay too late, you're essentially stuck taking a taxi back to wherever you came from.
Ship and Anchor
This is along 17 Ave. SW but it's not a place I would recommend as a prime destination, per se. It's a good bar that attracts a very local crowd, but I would only recommend it as a place to take a girl or have good quality beer. This place got decent crowds almost every night and was able to show World Cup games, which made it a prime destination on those days.
Nashville North
This is the tent inside the Stampede grounds. They always have live performers and the people here are inclined toward the country music scene. There is a mix of age groups here, but don't expect to hear anything other than country music and see anything other than two-stepping. Two-stepping you say? That's another topic altogether but I'd recommend having some basic knowledge of that dance style, or just learn it from some girl.
Marquee
Similar to Ranchman's except with a larger dance floor. I was never here in the night, so I can't say too much about it. It was decent on the bar crawl days, but it's a bit off the beaten path.
Roadhouse
I wouldn't bother with this place. It didn't seem that active when I was there, but if you're downtown it wouldn't hurt to give it a look.
As others have said in previous topics, you want to stay as close to the Stampede grounds as possible. The best places to stay in my opinion are downtown and the area around 17 Ave. SW called "Uptown". It's best to book this stuff a few months before, as the rates go up quite a bit for the week. I didn't spend more than $175 per night for my place, and there are certainly many options on AirBnB. You don't want to be too far west and have to depend on public transportation.
Transportation
Getting to Calgary isn't so bad if you're from the western US/Canada, since there are often direct flights to Calgary from some city in the region. Going from anywhere else requires some layover, and the most common one for an easterner would be Toronto since that airport has a lot of flights to Calgary every day.
Calgary airport is quite a bit north of the city center and one could drive there in about 10 minutes. There's a limited-stop bus from the airport (300) that will take you to the Calgary Tower downtown for $8.50. If you stayed outside of downtown, you'd probably have to take another bus though. One could also pay $50 for a cab, although I don't know where that would bring you.
Calgary public transportation is decent, but not great. There are several buses that go around the city, but they run every 15 minutes on peak periods, and stop running after 2:30 AM or so every day. The LRT trains run through downtown and by the Stampede grounds, as well as going to other parts of the city, but you'll probably have to find somewhere to even get to a station. The fare system is annoying at $3 ride with a system of paper transfers and tickets. Unfortunately, there's no weekly unlimited ticket, which I didn't like very much.
It wouldn't hurt to rent a vehicle, and this is especially helpful if you plan to hit up nearby parks or even Edmonton.
Food
There are plenty of dining options on 17 Ave. SW as well as 4 St. SW, not counting downtown. One can definitely expect to spend just under $10 on just food from a smaller establishment. The malls along Stephen Ave. (8 Ave. SW) have food courts and there are plenty of places along that strip itself. If you like burgers, you'll have a field day in Calgary since Alberta is known for its beef. I never went to any high-end places for dining, but in a city like this, I'm sure there's no shortage of them.
Safety
I found downtown and uptown pretty safe at night. There are enough areas where it was pretty damn silent, though. Definitely be a little attention at least.
One thing that also happens just about every night is the appearance of these random people playing music on the street. This is typically along 17 Ave. or near the Victoria Stampede station.
Stampede specifics
Your main points of interests during the week will be the grounds and outside establishments. The grounds are set up with a carnival as well as an 18+ tent known as "Nashville North". On weekends, lineups for this and other places start in the day, and on weekdays, expect to see people in the evening (think 5 or 6 PM). Entry to the grounds was $16 this year, and covers typically range from $20-40 anywhere else. Drinks average about $7.50 or so, and many people either pregame or sneak a bottle of some alcoholic drink for the lines. The airport has some duty-free shops, and it worked well for me. Figure out how much you're actually going to drink that week.
Another popular thing that people do is bar crawls. You essentially meet at a place, chill for a bit, and then go with other random people on a bus to three other establishments. They last about 6 hours and the two most common ones I saw were "Bust Loose" and "Student Tours". I did the former and didn't find it too bad. You can easily ditch the bus at any point on the tour and essentially get free entry to a location, which may not be a bad idea if you want to isolate a girl or leave a group with thin prospects. I found the tours to be nice, but nothing overly crazy.
One thing I would highly recommend is having a solid ID. Being one of the few American easterners in Calgary, many of the bouncers didn't trust my state ID, and I had to use my passport. I wouldn't recommend carrying around a passport, so be sure to have something that's a powerful identifier. The drinking age in Alberta is 18.
Locations
These are the places in went to at least once during Stampede.
Cowboy's
Probably the most popular place during the whole week. The actual complex is part of a casino in which there is a club (which is not bad itself); but the main party will be inside the tent that exists only during the week. The area is huge with multiple points for drink purchase and even food. The best talent I saw was here, but there's also a bit of a mean vibe here as this place gets a lot of out-of-towners and people with a bit of a mean streak. In my two times in the tent, I saw multiple fights as well as cops and security rushing to spots on one occasion. This place does bring in 50 Cent every year apparently, and Snoop Dogg also had a concert that I didn't go to.
Ranchman's
This is a bar that is located a good way south of downtown Calgary, but is reachable by the LRT train. It's got multiple bar spots and a respectable dance floor. I actually liked this place a lot since it had a good crowd, some talent, and was actually pretty fun. The main downside of this place is that it's far, and if you stay too late, you're essentially stuck taking a taxi back to wherever you came from.
Ship and Anchor
This is along 17 Ave. SW but it's not a place I would recommend as a prime destination, per se. It's a good bar that attracts a very local crowd, but I would only recommend it as a place to take a girl or have good quality beer. This place got decent crowds almost every night and was able to show World Cup games, which made it a prime destination on those days.
Nashville North
This is the tent inside the Stampede grounds. They always have live performers and the people here are inclined toward the country music scene. There is a mix of age groups here, but don't expect to hear anything other than country music and see anything other than two-stepping. Two-stepping you say? That's another topic altogether but I'd recommend having some basic knowledge of that dance style, or just learn it from some girl.
Marquee
Similar to Ranchman's except with a larger dance floor. I was never here in the night, so I can't say too much about it. It was decent on the bar crawl days, but it's a bit off the beaten path.
Roadhouse
I wouldn't bother with this place. It didn't seem that active when I was there, but if you're downtown it wouldn't hurt to give it a look.