Find Your Shows
This is probably the topic I get asked about the most, how to find the shows to begin with. You probably already know of a few craft fairs that happen in your area. Start a list. Check your local arts and events publications, chamber of commerce, newspapers, and art groups for lists of local events. Search online for your city or county's 'festivals', 'shows' and 'fairs'. Talk to people. I find many of my shows by talking to other artists. There are also publications out there that list events for us. I subscribe to Craftmaster News. It's cheap (about $50/year) and offers a printed book along with a great website that includes reviews and maps.
Once you find a potential show, contact the event folks and ask for an application and to be added to their mailing list. Keep in mind that most shows want you to apply at least a month or two (or longer) before the show dates. Smaller shows are more lenient and will sell a spot as long as there are openings. With any show, it never hurts to ask for last minute spaces... but be aware that last minute acceptance can sometimes mean a weird (ie crappy) location for your booth.
To organize my show list, I use my google calendar. When I find a potential show, I add it to my calendar along with the pertinent info including cost, type of show, web site, and whether the ap is online or has been requested. If I'm really interested, I enter the deadline on the calendar separately. When I decide not to do a show this year, I change the date to next year so I can find it when I need it next time.
For your first show, I would keep it small... as in costing under $100. You will not make millions at a dinky show, but you will have less invested to lose also. The smaller shows are a great way to get your feet wet, test your display, get feedback on your work, and network with other artists. Mostly, to just get out there and be seen. Don't be discouraged if you don't make much money at your first few shows. The real money is at the larger shows, which will be much easier to do after you have a few smaller shows under your belt. But DO listen to feedback and take note of the clientele and how they respond to your work. Every show will not work for every seller, it's a constant learning process.
As for what types of bigger shows are the best... it totally depends on your craft and your type of customer. When you consider doing a new show, learn all you can about it. Check out their web site, search for photos of the event, check out the people and the layout if you can. Will there be buy/sell or imports for sale? Or is it a juried artists-only event? Is there a rodeo, race, concert, or chili cook off? What is the area like in terms of demographics, income, types of businesses? Does all this info match with what you know about your best customer and the style of your work? The best you can do is make the most educated guess possible, and then go for it.
I love love love talking to new artists wanting to sell their work, it's so exciting! Getting out there and saying, "Here's me and what I do, love it or leave it." It's a little scary because it's different every time. It's a gamble. Even the same show can be drastically different from year to year. But every show is an opportunity to network with other artists and expose your work to a new set of customers. Learn and grow and then... find another show!