How I Started The Vineyard Series

How A 19 Year Old Created One Of The Largest Classic Land Rover Events In History

Five years ago, I started The Vineyard Series at 19 years old. At the time, I was an incoming sophomore at the University of Richmond in Virginia pursuing my degree in marketing. The pandemic had hit just months prior during March of my freshman year. When I went home for spring break in March 2020, I didn’t realize it would be the last time I would be in a classroom until August 2021 when I (admittedly) had no choice but to return to in-person classes.

During the newfound time over the pandemic, I made an effort to finally teach myself the skills I had been so interested in learning but never made time for. These skills were photography and graphic design. After many poorly taken and edited photos and even less impressive digital designs, I finally got the hang of software like Photoshop, Lightroom, and Illustrator. From there, I worked hard to put these skills to use. I started off doing digital car illustrations purely for myself and sharing them on social media. The more designs I posted, the more people reached out looking to have their cars drawn. As a result, I began to take on commissions while simultaneously continuing to make illustrations for myself. I printed stickers from these personal illustrations and sold them on Etsy. By June of 2020, I had a 10-week waiting list for commissioned illustrations and thousands of dollars worth of stickers sold. I come from an entrepreneurial family and I can proudly say that they were an inspiration for a lot of this.

In addition to my artwork social media pages, I also had photography-based ones where I posted photos I took of cars (primarily vintage Jeeps and Land Rovers) I saw. I ended up taking a photo of a 1980s Defender 110 and posting it on my Instagram. A few weeks later, the owner (who was a few years older than me) of that truck reached out, sharing that it was his and that he’d love to take some more photos one day. We did a couple of photoshoots over the course of a few weeks on Martha’s Vineyard, and eventually we got to talking about gathering a bunch of these vintage Land Rovers together. We had thought it would be the craziest thing to get 30 trucks together for the following summer.

With all of these new outside-of-school projects going on and the intense restrictions on in-person learning, I opted to take my entire sophomore year of college virtually. I continued to work on my commissioned artwork and stickers, but really wanted to make this vintage Land Rover meetup a reality.

Was this meetup going to have a name? Where was it going to be on Martha’s Vineyard? When would it happen?

Finding a name was definitely the hardest part in the very early stages of this first event. Was it going to be called something literal like “The Annual Martha’s Vineyard Land Rover Meetup,” or was it going to carry a more abstract name that invokes curiosity and leaves room for flexibility? After many days or maybe even weeks of thinking, I came up with “The Vineyard Series.” It was literal in the sense that it refers to a Series Land Rover on Martha’s Vineyard, but abstract in the sense of what is the “Series.” What I later found to be most important was the inherent flexibility that the format of the name provided. We found an awesome venue that was eager to host us (Nomans) and picked a date.

From there, we began to map out what this 30-Land Rover meetup would look like. We worked through the details and came up with a game plan. When it finally became time to announce the August 2021 event in February 2021, we were unsure of the response. Would there be 3 people interested? Hopefully 20?

After sharing it across my social media pages that I had been continuing to build, over 100 people reached out looking to get involved. Some were on Martha’s Vineyard, but the majority were around the country. How were these 100 trucks going to get to Martha’s Vineyard during peak season when the majority of ferries were already booked? Many said it wouldn’t be possible, but with patience and persistence, we moved over 40 vintage Land Rovers to and from the island for the August 1st event. I believe we had trucks from 7–10 different states join us.

The event ended up bringing together 84 vintage Land Rovers, making it one of the largest gatherings of purely vintage Land Rovers in the USA in recent times. The coolest part for me was being able to utilize these skills I had worked hard to learn in the year prior. The famous first-year t-shirt was a graphic I had created based on a photo I took. Some of the trucks I drew attended the event. Some of my sticker customers bought my t-shirts. It was truly a full-circle moment in so many ways.

The event itself was an awesome time, possibly my favorite event to date. Eighty vintage Land Rovers on Martha’s Vineyard in August, nobody had ever experienced anything like it. The energy and excitement of the inaugural event was unbelievable. I worked so hard, so thoughtfully, and it finally all came together.

My favorite memory from the event was the surprise police escort to South Beach. It had been loosely discussed ahead of time, but with the fast help of the amazing local law enforcement present at the event, we had a full 80-truck convoy through two jurisdictions, with several officers escorting us and blocking traffic. We ended up at the beach only to find the parking lot completely empty. That’s where the famous group photo was born.

I met countless friends at the event, many of which I now keep in touch with regularly. Evidently, so many others made friends within the event, which was even more amazing to see.

In fall of 2021, immediately after the inaugural event, I returned to in person school to start my Junior year and ultimately completed my degree in the year following, graduating in May 2023. While it wasn’t without some obstacles, I successfully finished school in four years while simultaneously planning and hosting the events for the better part of three of them.

When I finally graduated, I had more time and flexibility to host more events across the country. With the help of some local partners, we pulled off multiple events in Florida, South Carolina, California, Connecticut, Massachusetts, and Virginia.

To this day, The Vineyard Series network of events is a majorly one-man operation. I do everything from designing the product, to coordinating the events, to answering emails, to packing orders, to building the website, to managing the social media, to writing this newsletter, etc…

It is important to note that in doing everything mentioned above, I have had the tremendous support of my family and friends. I really could not have done any of this without them, so thank you to those who I know are reading this.

All of your support truly keeps these events going. Whether you’ve attended an event, purchased a product, or are just following along, your support keeps this unique community alive. I just launched some great new product and would love for you to check it out using the link below. Shop small this holiday season!

Thank you so much for five amazing years!

- Cooper