I always wondered what it would be like to quit my day job and play for tips in a tourist town. Last summer I found out. Well, I didn’t really quit my job, but I did make arrangements with my employer that allowed me to spend nearly every weekend busking on the boardwalk in Ocean City, MD. Before I could pull this off, there was some prep work to be done.

I bought a new sound system, one that runs on batteries. Ocean City does not provide electricity for guys like me, you have to be completely self-contained.

I learned how to pack my car so that I could carry everything I needed and still have enough room to sleep in it on Thu, Fri and Sat nights. Hey, if you have to pay for a hotel room, it will cost more to stay than you make playing! I found the Park and Ride, one mile from the boardwalk, to be the perfect solution. Risky? A little, but I never had a hint of trouble. For me, it was all part of the adventure.

If you’re going to be out in the ocean sun all day and sleeping in your car at night, you need a place to take a shower. I solved this problem by getting a Black Card membership at the new Planet Fitness that had opened across from the Park and Ride. This allowed me to not only take a shower every day, but to use their facilities to set up my laptop and do some work on Friday mornings (My day-job as an IT dude).

Ocean City is a 6.5-hour drive from where I live. Each Thursday, around 5PM, I would pack up my gear and my Golden Retriever, Rudy, and hit the road. This put me in Ocean City around 11:30 PM, where I’d stop at the Royal Farms convenience store next to the Park and Ride, grab some gas and grub and then head on over to the P&R to sleep for the night. The long drive was always a pain, but the anticipation of singing on the boardwalk the next day never failed to excite me as we rolled into town.

Friday morning, I’d use the nearly empty Park and Ride lot to throw a ball for Rudy and give him 30 minutes of exercise, and then he and I would head across the street to Planet Fitness. Rudy was always welcome and would lie quietly beside me at a table at PF until I finished my work. Around noon, I’d grab the aforementioned shower and then head out to enjoy the day.

When you’re new to the whole busking thing, it’s hard to know the best way to get started. There are many questions, like where is the best spot to perform, will there be competition, what time of day will work best, how do you keep from dying of heat stroke, what songs will work best with a mobile crowd, should I take breaks during the performance, what do I do with my dog while I’m performing!

Here’s what I learned.

The best place to play in Ocean City during the day is Caroline Street. There is lots of room there and this is where the largest crowds pass by. Caroline is just several blocks from the amusement parks and the pier. That part of the boardwalk is a major destination. It also has the advantage of being home to the only public restroom for a mile.

If you want to play on Caroline in the afternoon, when the crowds start to pass through, you have to get to there around 9AM and set up some of your equipment on the boardwalk in order to reserve your spot. Parking is severely limited and if you want to park next to the boardwalk, you have to beat everyone else. That means, arriving very early, setting up enough gear on the boardwalk so that the other buskers know the spot is taken, and then just sit around for the next few hours until it’s time to perform. This waiting alone would dissuade a lot of guys, but I have been undaunted. I’d sit in the air-conditioned car with Rudy and read a book or listen to podcasts until it was time for the show.

OC allows buskers to perform anywhere on the boardwalk as long as they don’t block emergency access to the beach. The rules are published on their website.

You don’t need a permit.

Performance spots are first come, first served, but you get to know the other regular buskers and where they like to perform. As a courtesy, we generally respect those preferences, but if there is someone playing in my favorite spot, I just move on up the boardwalk to another location.

Playing loud enough for the businesses around you to complain will buy you a visit from one of the many police officers who patrol the boardwalk. I have been visited several times and each time the officer has been kind and understanding.

Buskers are not allowed to sit on public benches to perform, nor are we allowed to use any facility owned by the city as part of the performance.

Dogs are not allowed on the beach or boardwalk unless they are service dogs. When walking the boardwalk, Rudy always wears his service vest. When I’m performing, I take the vest off and display it close by. Rudy lies on the public bench next to where I play. The rules about using the city benches for performances apparently don’t apply to service dogs. The police usually just smile at Rudy as they pass.

Rudy is an exceptionally well-trained dog. I started training him as a pup and we worked hard at it for several hours a day and for several years. His part of the busking experience is to just lie on the bench next to me while I sing. This he does with great aplomb, rarely moving and never reacting to the hundreds of people who stop to pet him. Several people have commented that they thought he was a stuffed dog and still others thought he was dead. I have actually had to prove to a few that he was indeed alive and well.

Rudy is a major factor in my success as a busker. I guess I do a respectable job singing and playing guitar, but there is no doubt in anyone’s mind that people are really tipping the dog. Parents send their children over with crumpled dollar bills, which they dutifully deposit in the tip bucket strategically placed next to Rudy’s bench. Adults who have had to leave their own dogs at home miss them like lost children and flock to Rudy, sometimes forming a line 12 deep. Through it all, Rudy never moves a muscle, happy to just lie on the bench and accept his “doggie lovin’s”. Many people tell me, “I like your music, but the tip is for your dog”. I tell them I’ll make sure he spends their money wisely.

I said before that Caroline Street is the best place to busk during the day, but after the first couple cool afternoons of summer, I rarely play during the day, opting instead to wait till around 6PM when things cool down. In fact, my favorite place to play is on 7th Street, across the boardwalk from Dippin’ Dots.

Daytime busking can be extremely hot and most buskers avoid it. There is also the matter of crowd dynamics. During the day, the beach crowd is mostly on the beach. Thousands of would-be tippers are sunbathing and not strolling the boardwalk. But at 6PM, the beachgoers have already gone back to their hotels, taken a shower and are now ready to see the evening boardwalk sites.

7th Street catches the crowds as they are heading toward the attractions at the pier, 13 blocks further down. The crowd mentality always seems to be more relaxed and less hurried than lower on the boardwalk. People have time to stop and listen to the music and to pet the nice dog. Many find a nearby bench to occupy where they can request some songs. As the sun lowers and the day cools, it’s easy to enjoy a little Billy Joel or James Taylor.

When I played in the bars, the music always had to be upbeat to keep the drinkers entertained. I seemed to always be searching for new songs that would keep the drinkers in their seats. In my younger days, part of my act was to sing songs from atop a bar table or a chair. It took me a while to discover that this isn’t necessary when busking. People either like you or they don’t, and if there are enough of them that do like you, you don’t have to make a fool of yourself to get their attention. I’ve found that I can play all the songs I really love, and enough people love those same songs that they will stop and listen. On the boardwalk, I call this “critical mass”. That means there are so many people passing by that the odds are in my favor that many of them will like what I do.

Critical mass is important. I know this because I played on the boardwalk the three weekends before Memorial Day and several weekends after Labor Day and the critical mass just wasn’t there, and neither were the tips. Before the summer months brought critical mass, I could not make enough money to make it worth the trip to OC. Discovering the theory of critical mass allowed me to relax and not work so hard to get people’s attention. Now I just let my talent and my dog do the heavy lifting.

This is never truer than when I busk in front of the Market House in Annapolis. There is a different dynamic at work there. On a beautiful Saturday afternoon, in the shade of the trees that cool the small Kunte Kinte park annex (across the street from the main Kunte Kinte memorial), the crowd is mostly well to do adults who have come to Annapolis for the weekend and have stopped at the Market House restaurant to enjoy the great food and the outdoor seating, which happens to share a property line with the Kunte Kinte park where I perform. Besides the people sitting at the outdoor tables of the restaurant, others occupy the benches of the park itself. Some brown-bagging it and others just stopping to rest for a while. These people are stationary, having detached themselves from the throngs of people who pass by on the sidewalk to have a meal while listening to the music. In this setting I have traded critical mass for a smaller crowd of generally wealthy listeners my own age, meaning they know the songs I sing and can afford to tip generously.

That last part doesn’t completely make up for the lack of critical mass tipping, but Annapolis is nearly three hours closer to home for me and I find the audience there makes singing very rewarding. Besides, I love the management and staff of the Market House, who have always welcomed Rudy and me with open arms.

I didn’t play in Annapolis as much as I might have liked last summer. Ocean City was where the money was, but I did sneak over to Annapolis a couple times when the weather in OC was bad and, more frequently, after Labor Day. Annapolis in the fall is awesome! That is also when the city hosts its two huge boat shows (one for power boats and the other for sail boats), both of which I was there for.

My last show in OC was Sunday of Labor Day weekend. I played in the evening until around 9:30 and then started the long journey home. The trip gave me lots of time to think about what I had learned from the experience, and I realized that I was not really sad to see it end. Mostly, I was just worn out but happy that I had experienced something few ever do and had fulfilled a long-term dream: to pit myself against a tourist town and make good!