Everyone knows you can play at bars, pubs, and restaurants. There are also many traditional music and entertainment venues such as theatres and festivals. I have tried to reach outside of these traditional venues and found some success book at the following types of places....
1. Golf & Country Club - I have had success booking special events, glow in the dark golf evenings, special dinners and tournament days. Most clubs have a licensed patio and are open to featuring some live music throughout their season. Look around your area and reach out the courses nearby. I suspect you will find a few would would love to have you come play some sweet, sweet music.
2. Farmers Market, or Orchard During Picking Season - Some farms or orchards will pay you to play during their busy season (early summer for self pick berries, and fall for Apples, Pumpkins). Just like the Golf Clubs, you will find many markets who will be having special events for families. If your music fits the bill, you might consider approaching a few of these farms. Also considering farmers markets, where sometimes you can "busk" for free, or you are able to pay for a full booth to sell music, merch and play some live tunes for the market goers.
3. Ski Resort Chalets/Pubs - Another seasonal business that hosts special events and most times have a pub or licensed area for drinking. This is a prime spot for the winter season in Canada (where I reside) or any place that has ski and snow resorts in their area. It's worth it to reach out before the ski season starts and see if you can plant a seed and talk them into entertainment for the patrons.
4. Marina or Boating Destination - I have had a few marinas approach me since they often have a common place or community centre where they will host dances and events. They also are interested in having live entertainment during their busy weekends. I have a marina in my area that is interested in booking me for all of the long weekend next summer, so, I can tell you from personal experience, a high end yacht/sailing club, or marina is not out of the question. Generally there is money kicking around for entertainment while people drink on their boats that are sitting in the slips. :)
5. Winery, Vineyard, Brewery - Once again, non-traditional and once again a high end place to book your gigs. There are constant tours and events going on at these locations all year round. I have played a two breweries which generally have a tasting pub, or bar right in the brewery. Many Canadians might know Steam Whistle Pilsner (an Ontario Craft Beer). I have played their brewery once and not only did they pay well, they also threw in a few cases of beer. Not to mention, I think there was about 200 people packed in the pub to listen to me jam out. It was one of my most memorable shows ever. Vineyards are similar in the fact that they sometimes have a small restaurant or wine bar where they will host music. Keep these places in mind and get your self out there.
I hear so many people complaining about not making any money playing music or cheap venue owners who won't pay for good entertainment. You need to cross them off of your list and move on to other places. If you can get into a few pubs and just one of the above list, then you are getting your name out there and maybe making a little coin.
Thanks again for your interest in my posts. By they way, you can check out 4 of the 5 songs on my new EP are exclusively here on my website. If you want to hear about the official release, follow me on Twitter and/or Facebook.