Concrete to Countryside: A Conversation with Cara of Caravan Trip Plan NYC
- 1 day ago
- 8 min read
On a rainy Saturday afternoon, I sat down with Cara Lash, founder of Caravan Trip Plan. At Mason Welles, a cozy coffee shop tucked along a quiet tree-lined street just off Union Square, I picked her brain on entrepreneurship, leaving her 9-to-5, and building a niche business from the ground up.
Jane: Hi, Cara. I am so excited to chat! What are you drinking?
Cara: A matcha with maple syrup, cinnamon, and almond milk. A lot of things going on.
Jane: I have never heard of cinnamon with matcha. I need to try that. I am sipping on a Dolce De Leche latte, and so far, I’m into it.
Now that we have our fun beverages, can you just give a little rundown of what Caravan is? Or maybe your elevator pitch?
Cara: My elevator pitch is - basically, we’re a New York City travel company that takes people from the concrete to the countryside. We take people on full-day escapes to go hiking, kayaking, skiing, and end the day with something relaxing like farm-to-table lunches, orchards, wineries, and you’re always back to the city by 6 pm!
Jane: This whole adventure being all in one day is such a plus.
What inspired you to start this?
Cara: So I have always been very entrepreneurial. I had my own customizable apparel brand in college.
Jane: Oh, my God, no way.
Cara: I’ll show you some pictures. It was called Lash Out. Another play on my name, because my last name is Lash. So yeah, I’m big on spinning my name.
Cara: I have always been really entrepreneurial, but fresh out of college, I went the consulting, 9-to-5 route. Honestly, because I felt like I kind of had to. I always knew that one day I would come back to being, or at least trying, to be my own boss.
I have always had a really big passion for all things in the outdoor world, like camping, glamping, and hiking. I've always been very in tune with that. I didn't really think that you could make much of a career out of it, because there aren’t a lot of jobs in that industry.
But I've always found that part of travel really fascinating, and I have done a lot of trip-guiding experiences in the past.
I grew up going to summer camp, backpacking through the wilderness, sleeping in tents, and cooking my own food. As I got older, I started leading those trips across Alaska, Canada, and throughout the U.S., guiding camping and road trips for campers ranging from 8 to 16 years old.
At the same time, I found myself craving a creative outlet beyond my nine-to-five. I started asking: What could I build on my own? Where could I be my own boss?
That’s when I realized there might be an opportunity to reconnect with the outdoor world in a new way.
Jane: What did the timeline look like from this thought to the beginning stages of Caravan?
Cara: Well, right after college, I was working in consulting and hated it, so I was just trying to figure out what I could do to start my own business. What can that be? And I said to my mom, I was like, “I'm gonna buy a campsite.”
Jane: Oh my god.
Cara: I was like, “I'm actually gonna buy one. And call it Caravan.”
Jane: So that was the true OG of Caravan?
Cara: It was the OG. I was 22 years old, right out of college, and my mom and dad were like, "Um, you're gonna need like $30 million to do that.”
Jane: And this was a solo venture?
Cara: Yes, I wanted to work in this very niche world of like camping and glamping. And obviously, there’s like only 3 jobs in that entire industry.
So I was like, what can I do right now that doesn’t need a huge cash investment?
And so I started thinking back to my days as a trip leader, leading camping and road trips across the U.S. and Canada. That’s when I realized there was a huge market for road trip planning because it can actually be really difficult. If you’ve ever gone on a road trip or tried camping, you know how challenging it can be to figure out camp availability and plan everything out.
Jane: And like what exact route to take, where to stay along the way, etc.
Cara: Exactly. It’s complicated. It would take me days to plan out all the logistics of my road trips.
So I started developing a web platform called Caravan Trip Plan to help people plan and book road trips:
Jane: Oh, wow. So that was the 2nd official iteration of Caravan.
Cara: Yes, and I was developing that for 2 years before I started the in-person Caravan.
Jane: And how did that go?
Cara: Tech is so-so challenging. And this was before ChatGPT. Which probably would have helped a ton/ the entire platform wouldn’t have been needed. Since ChatGPT can plan your entire road trip. But then, I moved to New York and finally launched the platform last April 2025.
Jane: Insane. So you kind of transitioned the tech platform into more of a way for people to connect in person via planned hiking trips that take you out of the city?
Cara: Yes, so now it is a lot different than how it started- there is no tech side at all.
So once we pivoted from the web platform, I decided to take out a trip with a bunch of friends and family as a marketing initiative to promote the platform.
Jane: Oh I love that. What feedback did you receive when you began marketing that trip?
Cara: The feedback made me realize even more that there was a need for it. People were really craving in-person experiences. Which is what led me to put the platform to bed and just focus on developing these in-person experiences.
So now we do hikes, kayak, and ski trips. Our first official trip was last July.
Jane: Ah, so cool. And crazy how much it has grown since then. Can you take us from start to finish through an average day trip?
Cara: Yeah! We always start in Washington Square Park with PopUp Bagels, coffee, and check-in. That’s where you’ll meet your guides and mingle with the other people on the trip before we load up the bus and head out for the day’s activity — whether that’s hiking, kayaking, or skiing.
The hikes are usually around 2.5 to 3.5 miles and geared toward beginner to intermediate levels. We’ll take a little break at the top, have some snacks, enjoy the views and conversation, and then head back down.
After the activity, we hop back on the bus and head to a second destination — usually something relaxing, like a farm-to-table lunch, winery, apple orchard, or beer garden. Then we’re back in the city by 6 p.m!
Jane: Such a great concept - getting to do all that in one day and just get a change of pace from the city.
As a founder, do you have any advice for someone with an idea/ business proposal who may not know where to start?
Cara: You’re never going to feel 100% confident, and it is a risk. But the risk is worth anything that comes out of it. Whether it’s a great success or failure, you’re going to gain something from the experience.
So go in scared. Do it. Something good will come out of it, even if it’s not what you originally intended — like me, I originally thought I was going to build a tech platform.
Some great advice I got from one of my business mentors was to start every day by asking yourself, “What is the one thing I want to do the least today? What am I putting off because it sounds miserable?” Then start with that thing. That’s what is going to move your business forward.
Jane: Such great advice for anyone trying to start a business, or even for motivation in general.
What would you tell someone living in a city who feels stuck in the concrete of it all?
Cara: Well, I did grow up in Michigan, which has so much great nature and greenery, so when I was moving to New York, everyone kept saying, “You know, there’s not a lot of grass and trees there, right?” I was definitely a little nervous about that.
That’s why Caravan events are so great for people who are new to the city — they give you a chance to make connections while also getting some quiet time and being outdoors. We usually keep the trips to around 30 people, so it still feels intimate.
Jane: I feel like being on a trip like this automatically gives everyone something in common. From my experience last weekend, it was so easy to meet really interesting people that you may not have crossed paths with otherwise.
Cara: Yes, definitely because you’re with them all day, too.
We’ve also seen so many friendships come out of our trips. I was actually with a girl last night who I met through Caravan, and she was telling me that she had just gone to London with someone she met on a Caravan trip! I think it’s so special to get to know a group of people over the course of a whole day while sharing these experiences together.
Jane: That is so amazing. What is next up for planned trips?
Cara: Up next, we’re doing a hike with Miranda McKeon. She is a content creator in the city who has her own company, Fill Your Tank, which makes conversation starter cards. So we are going to use the cards throughout the hike/ lunch to start conversations.
Jane: Oh, that’s the perfect activity for a hike.
Cara: Yes, exactly. And then the following weekend, we have a hike with a personalized meditation as the relaxing activity after the hike.
Jane: I love how it's different each trip.
Cara: Yeah, we try to put a fun spin on each trip.
We are also trying to tap into brand trips. Think Free People, Outdoor Voices, etc. It makes more sense for the brands to connect with the community outside of the city. So hiking, kayaking, doing the thing that their product is designed to be used for.
Jane: Last weekend, the Caravan trip that I went on was partnered with Splits59. A workout company that I own and love. So that drew me in initially as well.
So I do feel like it was such a great way for your company to attract people in, but also for a brand like Splits59 to do something with their community and get genuine content of their products in the wild.
Cara: And we are the one-stop shop for brands to be able to do that without having to think about the logistics of it all.
I also think that brands are now steering away from the influencer side of things and really diving into customer loyalty.
Jane: Totally. Is there anything exciting in the works or any exclusive information you can share with the Duvu followers?
Cara: We’re doing a singles trip this summer! So keep an eye out for that.
Jane: OMG, so exciting. I am writing that on my calendar.
Cara: Yes, please do. It’ll be 15 guys, 15 girls. We are going to do fun speed dating throughout the hike. It’s going to be really, really cute. I am excited to play matchmaker.
Jane: Well, I am so excited to keep up with Caravan and sign up for more trips! Thank you so much for chatting. Plug your socials, and where everyone can find Caravan.
Cara: Of course, I am so excited for this to come out!
Also, contact Caravan via email | info@caravantripplan.com
