My impression from having done outdoor fairs is that one should pick a handful of juried fairs (as Michael Smith intoned) and steer clear of the craft fairs. It pays to do your homework here. Certain demographic areas lend themselves to being less concerned with fine art (I once landed a spot between a face painter and copper lawn ornaments) and more apt to favor commercially accepted bucolic scenes (see Terry Redlin). Another thing to consider here is presentation. When hanging framed work outdoors, glare will drive you crazy, and your pieces take a beating regardless of how careful you are with them.
On the plus side, you do meet some truly interesting people.
There are a host of negatives concerning outdoor art fairs, but again if you select 5 or 6 good fairs each year, you are less likely to fall into the 'carney merchant' trap.
I have been doing the art fairs for about 12 years now. Here are my observations...
There has never been a worse time to get into the game than right now. The economy is bad and people are not spending money on art the way they did in the 90's.
There is a huge difference between the clientel that patronize a Fine Art Festival vs. the clientel that attend an Arts & Craft Fair. Generally speaking, people who attend the Fine Art Festivals have a lot of disposable income that they are willing to spend on art. People who attend the Art and Craft Fairs are looking to purchase inexpensive nik-naks to set on a shelf or give as a gift. My experience has been that there is very little money to be made at an Art and Craft Show and the POSSIBILITY of making significant money at a Fine Art Festival. So,...I have concentrated my efforts on the Fine Art Festivals over the years but still do a few Art & Craft Shows every year.
The Fine Art Festivals are very competitive to jury in to. The best resource out there for finding out information about these shows is a publication called the Art Fair Sourcebook. It is a compilation of the top 300 shows (based on sales the previous year) in the US. It gives you all the info you could want about any given show. The dates, the application deadline, the booth fee, the jury fee, the average sales of the artists that participated the previous year, the number of artists spaces in the various mediums, what the people that attend that show prefer as far as traditional or more modern-avant garde. Any one who is considering getting involved in this should seriously consider purchasing a current copy. As far as I am concerned it is the bible for those who do these types of shows.
One of the real problems with these Fine Art Festivals is getting in! As I have already mentioned, I have been doing this for a number of years now the top tier shows were elusive for many years. I now get into about 20% of the shows that I apply to. My acceptance rate started out much lower than that. I have been accepted into four "Top 10" shows over the years. Three of the four turned out to be quite lucrative. (Between $8,000.00 and $10,000.00 in sales over a weekend) One of those shows (a "Top 5" show was $700.00 in sales....a loss after you add up the booth fee, jury fee, travel, meals...
My best show ever has been right at $10,000.00 in sales my worst show was a loss of $800.00. Both my best and worst were Fine Art Festivals as opposed to art and craft fairs. Finding your niche market (the locations where people appreciate your work enough to spend money on it) has proven to be a challenging task. There are very few Fine Art Festivals in the country and whole lot of art and craft fairs.
Since 9-11 it has turned into a numbers game. You can be profitable if you do enough shows. Pre 9-11 I used to do about 10 - 12 shows per year. My sales average was just under $3800.00 per show. Post 9-11 I am doing 20 - 25 shows per year with a sales average of about $1600.00 per show. Obviously that means I have to do more shows and spend more to do them. (travel, lodging, meals...)
Some other observations are... color photography sells much better than B&W at these events. Photography is still very much considered a second tier art form. (The "Anybody that owns a camera can do that." attitude) People will spend thousands on oil paintings, sculpture and a host of other mediums, but still have a hard time spending $100.00 on photography. It always strikes me as odd when people come into my booth wearing designer clothes and shoes that cost several times more than some of the pieces that they look at and really want ...but they aren't willing to spend $80.00 on something that will last them the rest of thier life, ...so they walk out in their $200.00 shoes that will end up at Goodwill some day in the not too distant future.
The final thing that I will address is the start up cost. It is not cheap to get started. You will need a white canopy. I caution you...do not scrimp on a cheap one! You will be sorry the first time you encouter rough weather at one of these events. Craft Hut has been around a long time and is considered to be the best thing out there. It is very sturdy and water tight. It takes a long time to set up compared to the other canopies but it is well built. I have seen so many EZ-UPs destroyed (along with the work that was inside it) overnight in small storms. If you are going to do this make sure you protect your work with a good canopy! My set up cost about $3000.00 ... the Craft Hut canopy, Pro Panel display walls and browse bins and track lighting. Then of course there is your inventory. Pre- 9-11 I traveled with about $18,000.00 in inventory. Now with sales down I travel with about $12,000.00 in inventory. These shows are very much based on impulse buys. If you don't have it on hand...they probably won't be willing to do it as a special order. People want to walk out with their purchase. Hence the need for the large inventory. Your prints will need to be matted and protected in plastic for your browse bins. The framing costs to fill your booth with an attractive display of your work. You will need a large framed print or two to draw people into your booth, and a number of smaller prints to fill the space. People will purchase the unframed small matted prints, ...but you need to have the big framed stuff hanging to attract peoples attention. Today at the art fairs 16x20 is not considered big. Something big enough to attract attention starts at about 20x30...bigger is better though many sport 30x40 and 40x60 now. You are competing for the attention and the bigger stuff gets the most attention. Booth fees today range from about $200.00 to $1500.00. This is payable upon acceptance to the show which is often 4-6 months before the show.
Finally, you need some way to get all of this (canopy, display walls, lighting. and inventory) to the show site. Many drive extended vans. I am seeing more and more box trucks these days. I drive a F350 Diesel and pull a trailer. You can rent a trailer from U-Haul when you are starting out, but eventually you will want to purchase one. The rental fees over a year of shows will be more than the purchase price of descent trailer. Don't forget to figure in your lodging, meals and fuel to the cost.
This is just the tip of the iceberg. I wont take up any more band width boring this community with all of the minutia of doing these types of events. I have well over a decade of experience in this arena. I'll be glad to answer any other questions anyone might have.