New England bike tour guide



Guide: Dennis Lennox, Miami Beach, Florida

Meet Dennis Lennox. He’s been leading our Canadian and Berkshires adventures for over 13 years and has a pretty exciting life both in and out of cycling season.

Q. How long have you been leading cycling tours?

A. My first official bike tour was in 1987. I was a high school teacher in Boston when a request looking for teachers to lead bike tours for high school students ended up in my mailbox. I interviewed and got the job—30 days in Europe with 14 high school kids and a recent college grad as my assistant. It was a blast and I was hooked.

Q. What do you love about the routes you lead?
A. I love all the routes I lead, but Prince Edward Island and Nova Scotia are so special, way off the beaten path. Folks are so welcoming and happy to see you. Drivers are relaxed and stop when they see you crossing an intersection. It’s a step back in time to when things were a lot slower. The scenery is soft and gentle—after a few days the cyclists become soft and gentle, too. It’s a real vacation!

Q. What is the most unique thing about the routes you lead?
A. Hands down there’s no place like the Berkshires. When I lived in Massachusetts, I always went to Cape Cod for the summer. But then I lead a tour in the Berkshires, and I was blown away by the beauty. The Rockies have a certain grandeur, but the Appalachians have class and history. So much of our early history took place here, it’s loaded with natural beauty, and it’s New England at its finest—old mansions, rolling farms, and really great restaurants. (The food’s my favorite part.)

Q. What is your most fun/interesting/ crazy memory of leading tours?
A. I’d have to say my favorite memories are of all the wonderful, fun, and interesting people that I’ve met over the years. Interesting conversation, great belly laughs, and new friends…those make the best memories.

Q. When did you start cycling?
A. As a kid, like most of us. My bike gave me freedom and nurtured my need for adventure. I’ve never really left cycling. When I started teaching after college, I would always start summer vacation by packing up the bike and hitting the road for a tour. I was able to let everything go and relax into summer. Ahhhhh!

Q. Why do you keep doing it?
A. Because I still love an adventure and it makes me feel like a kid again.

Q. What do you do in the off season?
A. I live in Miami Beach where I have an Acupuncture practice. A few years ago I did a stint in the Peace Corps in Thailand and fell in love with the country. I try to spend three or four months there each year. While in the Peace Corps, I bought a Dahon folding bike to get around. Each year when I return, I bring that bike with me. It holds two panniers and the airlines don’t charge me to take it. I land, unfold it, put on the panniers, and I’m off to parts unknown.

Q. If you could cycle anywhere, where would it be?
A. I’d like to ride down under—Australia and New Zealand.

Until July 15, we're offering a $200/person discount on our Autumn in the Berkshires tours.