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I think age is a big factor in meeting people when traveling solo, when you are young, staying in hostels, it's quite normal, or at least it was for me to meeting people on the drop of a hat and head out for a drink. That changes when you start reaching middle aged in my opinion...it's not so easy to meet people, even staying at hostels.

There are some organizations that could be useful, Hash house harriers, expat social clubs which are typically online...or one I find quite good is going on an organised tour or one day cooking course and you will typically meet people that way.

I know I've said this before, but take a book for the evening meal awkwardness.  If you're lucky, you'll meet someone who is in the same boat and share a table, but often you don't (or don't want to) and a book helps you pass the time between courses.  Alternatively, eat street food!

I don't have a distinction between levels of difficulty in meeting people in cities or out of them; in Panama City I had a trip out to the Canal with a couple of Mormons before they headed off to a conference, in Skopje struck up a conversation with a fellow solo traveller on the airport bus and in Nairobi, stayed at a hostel with a campsite in its grounds which had communal dining.  I always make small talk with people with whom I come into contact and often that leads to something.  If it doesn't, fair enough.  I like my own company!

Mattyboy and Julia both make some good comments.

The key thing is that you have to be (a) unafraid to strike up conversations
with anyone who happens to be around, and (b) content with your own company.

Age is definitely a factor - not many 60-plus-year olds travel alone, and I am
always cautious about getting "lumbered" with those that do. Younger
people share this apprehension, and are cautious about getting lumbered with
me. If you can hit it off, it can be great; if not, the book (or nowadays
Kindle) can be a great solace.

Of your sample cities, Lyn, I have not been truly alone in any except Rio. And
there - as elsewhere in Brazil - if you like to dance, there are always people
who will join you.

As for elsewhere - in Gambia I picked up a bumster and spent most of the week
with him learning a lot about Gambian life and society from him (see http://www.wanderlust.co.uk/mywanderlust/members/alan-taylor/experiences/gambian-highlights_4950); in Tobago I got chatting to a local restaurateur and his mate, and separately to a family that were doing much the same things as me, and those were both
interesting contacts; in Crete another restaurateur filled the role; in Antigua
I didn't meet up with anyone in particular until I shocked a friendly local by
walking to the place a steel band was playing and he took me under his wing to
prevent me coming to harm in dodgy areas.
So you play it by ear, and keep an open mind as to the opportunities.
As for being a man - at my age I don't think it matters; (much) younger men might find that local male hormones kick in aggressively, but I wouldn't know!

Very nice information! What a nice style of sharing information.

I travel alone because I like it that way. I don't go out of my way to "meet the locals", it just seems to happen more easily when you are on your own than if travelling in a pair or a group.  I recently spent three months travelling central America, two weeks of which was with an organised group tour.  Having got used to being alone I felt quite removed from the country when moving through it with a group - not one conversation with "free" travellers or local people - get me out of here! 
Here's one frustration and one idea then. Frustration - As a keen hiker, and wanting to get off the beaten track, it is difficult and expensive to join local ad hoc tours - prices are usually based on two people and local operators seem reluctant or unable to slot a single traveller into a private group. There are trips that it's not a great idea to do alone.
Idea - I pick up local papers or find newsletters on the web, sometimes run by local expats or experts (history, archeology etc), where you can find details of upcoming events and interest groups. There are often local walking groups for instance, who do local area walks focused on history or architecture - a great way of finding hidden places, and learning more than you find in the guide books, especially in cities.  I have been to cookery classes in a local home organised as part of local women's group - and then you get to meet people which leads to other invitations, such as a local writing group who had an evening reading some of their work, a pop up restaurant (though they had never heard of this term) for breakfast, or someone passionate about their locality who took me on an impromptu sightseeing trip to some hidden rock paintings.

PS, I am one of those pestiferous over 60s Alan, definitely allergic to any lumbering activities!

   Really helpful suggestions above. I would agree that it is important to be comfortable in your own company, and to see the prospect of finding friends as an added bonus, rather than the objective of the trip. I'd also agree that travelling solo, rather than as part of a tour, opens up far more opportunities to befriend local people, rather than the other people in your group. Each to their own, though. My Mum loved going on tours for years as a single, right into her late 70s; she didn't meet many people with whom she wanted to continue a relationship after the holiday, but the one or two friends she did make were friends for life.     
   I travelled extensively on my own for work, but there were usually overseas colleagues around, and any time I could get on my own I valued. I used to take a book into restaurants, but often just left it on the table while I looked around. People watching in restaurants can be a lot of fun. Waiters seem to go out of their way to talk to you if you look receptive, and I had lots of amusing chats.
   Of course, as a single woman you (boringly) have to be on your guard for persistent men (mind you that can happen at home if you're on your own), but I was pretty good at putting them off by my unresponsive conversation, body language, facial expressions and finally, if nothing else got through, a firm "get lost" kind of sentence.
   I stayed in LeSport, St Lucia (in one of my previous lives) which was a resort dedicated to sports of every kind. I went on my own, but within minutes made new friends. Holiday that have a particular group activity/interest at heart are obvious choices for singles (trekking, history, culture, 'learning' kinds of holidays).
   If you're keen to hook up with people in a city (or anywhere), then why not stay in homestays or B&Bs? There is quite often one big table for sharing food together, and it's a natural place to start a conversation with the owners, and the other travellers. Or go one stage further and couchsurf!

Sorry, I forgot to say that at LeSport (I went three times) I made friends with the instructors and trainers, all local boys and girls. In the evenings a few of us singles would break out of the compound and go with them to their flats, and dance the night away at the local "jumps ups". They were much more relaxed out of uniform. It was brilliant fun, and those evenings were much more interesting than the ones spent at the hotel. I guess I'm saying that even in resort hotels you can find a bit of local flavour if you look for it.

As a single male who frequently travels alone, one the biggest irritants I find, in some countries, is being continually approached by prostitutes. In Bangkok, I was asked, outside my hotel after breakfast in the morning, if I was “looking for business.” At a souvenir shop in Lima, a young woman informed me that she provided “massage and other thing.” In Cuba, I was followed up from the hotel bar to my room by a local girl asking for a drink of water, as if water wasn’t available elsewhere in the hotel. OK, they’re not usually difficult to get rid of (saying “yes, but I don’t think you could afford me,” usually does the trick!), but I just find it annoying that unaccompanied men are seen to be necessarily on the lookout for “other thing.”
Another hazard of travelling alone, especially as part of an organized group, is being latched onto by someone you really don’t want to know who won’t take the hint - see my Experience Driven Bonkers In Honkers.
In general, though, I enjoy the major advantage to solo travel, in that I can decide where I want to go, what I want to do and when.

I disagree with the comment that age is a factor, having just got back from South East Asia partially in company and partially solo.  I picked up people of all ages and I'm shy and not good at striking up conversation - you do just have to force yourself.  Sometimes you can catch someone's eye and smile.

Use local public transport if you want to meet locals and ask if you're on the right bus/train etc - even if you know the answer already.  It's a bit cynical but people like to feel they've helped and it breaks the ice.  The old adage of have pictures of where you're from and your family is always good.  People in countries without loads of technology love using it - ask a local to take your photo in front of a landmark or somewhere.  It makes a change for travellers not to take a picture of them and sometimes they do ask to be in a photo with you.  Show them the used result and be really positive and excited that their photo is great.  Basically - be positive about people you meet and their country!

If you want to meet other travellers, use traveller transport and stay in hostels, either in a dorm or, if you prefer to be in a private room, stay somewhere that has a bar attached or organises day trips that you can join.

The biggest and simplest thing you can do (and it works almost every time), is to smile and say hello - that's all it takes.  Remember to be interested in other people too - nobody wants to solely all about your travels - they're doing the same thing and will want to share too - ask questions, take recommendations, make recommendations and remember you're all in the same boat. When you're sitting in a bar dithering about saying hello to the solo traveller next to you, chances are they're having the same dilemma.  A friend of mine went to one bar where the barman made all the single travellers sit next to each other. Be proactive about it and introduce yourself!

You meet more people by doing things than by looking at things, so some form of common interests activity breaks up the isolation.

Smaller scale adventure cruises tend to bring people together. A couple of weeks with 50 - 100 people and ad hoc seating for dining means you tend to meet a range of people.

Shared table type restaurants make it difficult to avoid talking to people, even if your grasp of the local languate is limited. In Berchtesgaden, I ended up using very basic German to discuss mountain running (which was the purpose of my trip), early music, Hitler's education policy, dog breeding and the empty nest syndrome, and Scotland's attitude to England at football matches. A couple of days later, at the end of the race, two of the people I had met were among the spectators, loudly cheering me on.

Headgear, or other slightly unusual clothing can provide a link. In the Mani I briefly talked to a couple of Swiss ladies who were very envious of my map, since local maps were difficult to come by at the time. A few days later, they gave me a lift which avoided some very boring road walking, having recognised me by a rather fetching straw hat I had bought, having forgotten to pack something more conventional.

Smiles always work. As the only female in a remote Greek taverna full of backslapping male hunters I was having dinner, writing my diary, and periodically smiling agreement to the spare chairs from my table being taken. After a while, the demijohns of home made wine appeared, and glasses were offered. I ended up having a very pleasant and unthreatening evening, combining some very basic conversation and some very drinkable wine. 

Thanks all. Some useful stuff in there, and some ideas I would never have thought of (distinctive headgear!). I hope you don't mind if I quote one or two of you in the article. Thanks again.

I think it's important to differentiate/identify why you are a lone traveller as that will have a direct effect on how you approach things. There is nothing more frustrating than being "adopted" by other people when you want to be on your own and you need to work out strategies to politely extricate yourself from these situations. I enjoy solo travel because, in my experience, it is slower paced and I can be selfish with my itinerary choices.