Christine Hastings on the Jolly Trolley in Rehoboth Beach and Dewey Beach, Delaware

Christine Hastings owns and operates the iconic Jolly Trolley in Rehoboth and Dewey with her husband, David, and her stepson, Turner. Christine has driven the trolley longer than anyone else, and has been known to belt out the Jolly Trolley song to the tune of the holiday staple, “Deck the Halls.”

DT: When did you become involved with the Jolly Trolley?
CH: The Jolly Trolley started in 1970. A group of locals wanted to literally share the atmosphere of this area. Let the sea breeze in your hair, smell the ocean, hear the sounds and just have a nice cruise around the area.
That went on for numerous years and it had many owners. In 1991, the owner at the time approached David and I. David was captain and owner and operator of the Atlantic Coastal Advertising sign boat, which is the electronic sign boat that ran up and down the coast.
The owner said, Listen, “I just bought the Jolly Trolley and my mother loves to ride it,” but he was looking at it as an advertising investment. He did not plan on getting into the transportation. He said, “Hey, can I subcontract you to sell the advertising? And by the way, do you know anybody who wants to drive this?”
At the time we were in the advertising business and we were not planning on getting into transportation. David’s first thought was, Oh my goodness, this thing’s going to be high-maintenance—and also dealing with DelDOT and other things that weren’t quite in our business plan—but, hey, let’s give it a try.
We started to drive it in 1991 as a management team for the previous owner. And this part’s pretty important to the growth of the Jolly Trolley shuttle as we know it today: We actually ran the shuttle route between Rehoboth Beach and Dewey Beach at no charge. And that was because we were in the midst of putting our application together to submit to the state for a certification of public necessity and convenience.
In order to do that, you have to do all sorts of paperwork. So we ran it for the season to feel out what would be a good route, what could definitely be done on a regular basis, and more importantly, work with the town of Dewey Beach and the city of Rehoboth Beach and find out where the stops could be for convenience, safety and just overall good headway with the route.
Once we locked into where the stops would be and how the route would go, we then submitted the application to DelDOT. We then put together the corporation, which is Transit U. Inc. That was in the winter of 1992.
So by the summer of 1992, the Rehoboth Beach-Dewey Beach shuttle service, which runs a basic schedule every half an hour, leaving Rehoboth Beach on the hour and half hour, starting at the top of the Avenue at the boardwalk.
And then at south Dewey Beach, at Dickinson Street on the bay, at quarter after and quarter of each hour. There are about a dozen, plus or minus, stops in between the two points. They were condoned by Rehoboth and Dewey.
We have added a stop at Robinson Drive at Silver Lake Bridge and that came after many years of feedback from the community and working with the local neighborhoods. That was about three years ago. But other than that, it’s been the same ever since 1992.
Again, I’ll stress that first year in 1991, running it at no charge because we couldn’t charge anybody until we had the proper paperwork in line and had that certificate of public necessity and convenience from the state.
So that was 1992.
The Jolly Trolley has been around since 1970. Transit U. Inc. has been the owner and operator since 1992. At that point we only had one Jolly Trolley. We then over the course of the next couple of years, we added another trolley, then another Jolly Trolley.
In 1994, we got a street license for charters. Even though the Jolly Trolley had been doing charters and special events since 1970, the state then required that there was the necessity to have a state license for that.
So since 1994, we’ve had basically two identities: the fixed route, mass transit, which basically is just that, carrying lots of people with a fixed route with convenient stops, again focusing on convenience and safety.
As far as since 1994, we’ve done hundreds of thousands of weddings, special events. I won’t get into the who’s who of weddings, but we’ve had folks who call us a year and a half in advance and say, “I need, I want the Jolly Trolley in my wedding.”
Starting in 2000, we started adding passenger vans to be part of the Jolly Trolley itself, giving more seating capacity. Also the vans can be used for charters and special events.
In 2009 we added a couple of small buses. Again, adding to our fleet, evolving. The whole idea of that jolly transportation.
And then in 2010, we added a Jolly Trolley car service. It is technically a limousine service. We do anywhere from special events, nights out, but also airports. Because of that, there are many different sizes of Jolly vehicles that can be used for somebody’s special event or charter. We customize to what their needs are. It’s grown over the years.
People love the Jolly Trolley for what it is. It is a convenience. It is a mode of transportation. But, most importantly, it’s a great way to just chill out, let somebody else do the driving and enjoy the area.
On the fixed route, the open air let’s you feel the breeze, smell the ocean, see the sights and be social with your family.

DT: What about the song?
CH: If I may, I have a song that I sing regularly to the troops, meaning our Jolly riders, which we call them affectionately. It’s a little play on a Christmas song, but it all works. Why this song is so important is because it incorporates the general feelings of the Jolly Trolley: jolliness, convenience and group and/or family socializing and togetherness in their transportation.

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Tis the season to be jolly.
Group joins in: Fa la la la la, la la la la
Just relax and ride the Jolly Trolley
Fa la la la la, la la la la
Parking, driving, why bother? You can even bring your father. (That always brings a little round of applause.)
Tis the reason to be jolly.
Fa la la la la, la la la la

I love driving the Jolly Trolley. The Jolly Trolley and Transit U. prides themselves in having, not just big vehicles and good, safe drivers, but people people. People who are there to help you out and be there to help you with your transportation needs. It has grown and we can’t do it without our jolly riders. It’s funny because after doing special events and weddings, everybody is always thanking each other, even on the fixed route: “thank you, thank you.” And it goes back and forth. We thank our jolly riders wholeheartedly. We love to help them. To me, I love to help people and see them sitting back and enjoying their vacation and socializing and having fun with each other: singing, clapping. Of course, with noise ordinances, we have to keep it down. But it very much brings a lot of smiles.

DT: Name one of the coolest things about the Jolly Trolley.
CH: One of our biggest things we like to do on the Jolly Trolley is wave. We’re always waving. We’re waving to and from on our fixed route and the feedback is just wonderful. People wave back. They may have no intention of ever riding the Jolly Trolley, but they definitely look for that jolly smile and that wave. It’s a great thing for the community and just all around because I think our world and community in general need that. And I’m not being gushy here. I’m being very honest. Everybody needs a good wave and a smile every now and then because the world is the way it is. And to keep it moving forward, we all have to take that little extra effort and make things a little more comfortable and jolly.

DT: Have you ever had to fire somebody because they wouldn’t wave?
CH: No. But we have had to remind people that they do need to do that. When we’re interviewing and looking for drivers, we’re looking for people people. We want people who aren’t just commercial driver licensed drivers. We want people who sincerely want to be here and are helping people out. In Jolly Trolley land, we want people to enjoy life. Forget about that parking meter or the electric bill or the uncle who is driving you crazy or just life in general. Everybody keep moving forward and keep a good attitude.
By the way, it was my husband, David, who really started pushing the waving. We’ve always been waving and smiling, but now it’s part of the uniform. It comes sincerely. If somebody has a hard time with it, then we have to regroup with them and get them to understand that it’s all part of the Jolly Trolley.

DT: Do you get to have a fun summer?
CH: Summertimes are very intense. Personally, I always look forward to them because you get your Jolly Trolleys on track, literally and figuratively, and you just roll, you just go with it. Eight a.m. to 2 a.m. We have a wonderful staff.

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DT: Let’s talk about the infamous late-nights on the trolley.
CH: When the Jolly Trolley started, yes, late-night was a big part of the Jolly Trolley. Over the past couple decades, it has definitely become less of a priority. What we call family hour, that 5 p.m. to 10 p.m., where the families are going back and forth between Rehoboth Beach and Dewey Beach, that’s when the Jolly Trolley is definitely at its best and at pretty full capacity. Our daytime has picked up quite a bit—those folks who don’t want to be on the beach all the time. We also have folks who just want to use the convenience of traveling between Rehoboth Beach and Dewey Beach.

DT: We’ve heard some pretty crazy stories through the years. Anything you can talk about?
CH: There’s nothing that you can’t imagine. Two things that bother me the most in life in general and on the Jolly Trolley, is inconsideration and greed. And with anything in life, it’s human nature that you’re going to have those two elements. Late-night, everybody wants to go home at 1:15, so it can get rather jolly. Yes, there is singing. “God Bless America” is a big one. “Bye, Bye Miss America Pie,” “Buttercup.” I’ll lead the jolly riders in “Summer Loving” from “Grease.” Rumor has it there are fights on the Jolly Trolley. I can literally count on maybe two hands over the past two decades how many fights of any value that we’ve had.
Jolly riders want their Jolly Trolley to be jolly, they want it moving forward. If we do have any incidents where somebody is being belligerent, or not jolly, we just stop. We ask for local authority help. And jolly riders will ask that person to please get off the Jolly Trolley. They may use a few words that we do not. It works together. There have been people who have just shown that they were not going to be cooperative or jolly. And they are not given service. We do give them different options. One is to chill out, go grab some pizza and drink some water, reassess and we’ll be around again and maybe your attitude will change. Again, this is so, so minimal.
Most of our late-night activities are very positive. I honestly sometimes feel like Mom picking up the kids. We find that if the Jolly Trolley is that positive, reassuring, reliable source; that they know that they can have a great time and they know they are going to get home safely.
I have a degree in psychology, so it kind of tickles me pink when folks who might have some difficulty in communication late-night … and I can still figure out, by just asking a couple of key questions, where it is they need to go. We stay consistent on the Jolly Trolley. We don’t want to confuse people.

DT: I hear the Jolly Trolley may have been the scene of some romance through the years.
CH: I can tell you that two weddings have come out of a scenario like that. Where male and female had a great time at the Rusty Rudder deck or at The Starboard or any of the venues and they follow each other onto the Jolly Trolley, get to the next destination and realize, Wow, I don’t really need to be here. “Can you take me back to Dewey Beach?” “Sure. No problem.” And lo and behold, months later I find out that they chartered us for their engagement party. Down the road they charter us for their wedding. And then they turn around and charter us for their child’s birthday party. To me, that’s the epitome of really giving back and having a good business.
I love it. I tell people they literally and figuratively fuel me. I’m a people person. I really enjoy the whole philosophy of the Jolly Trolley.

DT: Can you talk about some of the famous people who have ridden the trolley?
CH: We are the Nation’s Summer Capital. We have had quite a few law enforcement personnel who are way, way up there who have been passengers on the Jolly Trolley. It’s interesting to watch them watch the jolly riders.
One of my favorites is Michael Jordan. He was in the area listening to music at Sydney’s Side Street. He got on the Jolly Trolley. Our driver did not ask him for an autograph. He did get charged. He did pay his fee. He did have to duck to get in.
We’ve had many, many different faces and names. And to us, they’re just jolly riders. And respectfully, we don’t make a big deal about them because they want to enjoy this area.
Bobby Labonte’s NASCAR team. They were hilarious. They had all their input to different ways things could be designed. A local gentleman who used to play for the New York Giants. We recognized each other, but I could tell he didn’t want me to make a big deal about who he was. The Weather Channel.

DT: I understand that employees of local businesses get a break on the trolley.
CH: Since 1992 we’ve had a wonderful employee policy, at a minimal cost, in uniform, employees can travel on the Jolly Trolley. We stress the uniform to pull that team together, that community idea. You have the Grotto Pizza, the Fins, different establishments that their staffs, for parking reasons and convenience, will travel on the Jolly Trolley. While they’re on the trolley, Joe and Martha and their family may ask the Fins staff member, “Hey, what’s Fins like?” And we find that it just pulls that whole community service idea together. It helps the employees out, it helps the employer out, but it also helps the visitor who is asking questions and wants to have some local and/or summer employee feedback.

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DT: The advertising signs seem to be a part of the trolley’s identity.
CH: Yes. Some of our advertisers have been on for decades plus. We have advertisers who I actually have to recommend that they updated their panel because it’s been on there for 10 years and it’s needing a little update. Grotto Pizza is a huge supporter of the Jolly Trolley. Again, that teamwork idea. People refer to the Jolly Trolley as the Grotto Pizza Trolley. The Jolly Trolley loves the idea that one of our convenient stops happens to be at Read Street in Dewey Beach at Grotto Pizza.
When we put those stops together, David and I walked around the town of Dewey Beach and the city of Rehoboth Beach and asked, “Where can we have these mass transit, fixed-route stops? These are big vehicles. We need to have stops where we can pull in safely, have our jolly riders get on and off and it’s convenient for traffic flow and the whole bit.”

DT: So you still drive the trolley?
CH: I’ve been driving since 1991. So has David. My stepson, Turner, David’s older son, now has come into the business officially. He is a principal co-owner. Turner has been driving since he was a graduate of the University of Delaware. We all put in our time driving. It’s important to us. Not only as principals are we out there to be approached and to see what’s going on, it’s just a really important part of any small business, of being an entrepreneur, to have your finger on the pulse. I have been driving the longest, due to the fact that David was driving the ad boat almost at the same time I was driving the Jolly Trolley. Up at the boardwalk, every once in a while we would cross paths and I would wave to the sign boat and he would wave back.

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