The accidental tour guides: Rich Taylor and Jean Constantine’s Vintage Rallies

Some ventures are plotted to the last detail, with business plans, P&l predictions and long-term strategies. According to Rich Taylor, who founded Vintage Rallies with wife Jean, “We’ve never planned a thing.”

Doing the unplanned seems to be a pattern for Taylor, who started out as an aspiring engineer then earned a doctorate in art history that he’s never used. Taylor — who has raced motorcycles and cars professionally and for fun — built a career as an automotive journalist, beginning with Car and Driver. Jean Constantine, meanwhile, attended the Rhode Island School of Design, where she earned a degree in illustration. An accomplished photographer and designer, she was well prepared to partner her husband on a variety of book, newspaper supplement and magazine projects.

One of those joint projects turned out to be a life-changing event. As Taylor recalls, “In 1991 we did an article on the Mille Miglia Storica for Town & Country. Organizer Costantino Franchi gave us a great experience. It was exciting and fun, but there was no support for the 350 cars and you spent three days driving around Italy in a huge traffic jam. It was exhausting and you never caught up on sleep.” In other words,” says Taylor, “it was wonderful and Italian.”

When the couple returned home they thought, “We can do something like this, but more fun.” The pair was very familiar with Jean’s native Vermont and knew it had wonderful roads and great hotels. The first New England 1000 was held in 1993 for 23 couples from all over the country.

Most of the participants were people Taylor knew through vintage racing or were Ferrari club acquaintances of friend Jim Skyrm, who introduced the Taylors to then-Gov. Howard Dean.

With the full support of the governor and the state police, that first New England 1000 was a resounding success and raised more than $25,000 for charity. Along the way there were valuable lessons learned by way of careful preparation, engaging state officials early and supporting small charities for which modest donations would make a huge impact.

When asked when he realized the rally business was lucrative enough to be his primary livelihood, Taylor just laughed, explaining that it isn’t their livelihood at all. “We pay our temporary employees and cover our expenses. The rest goes to charity — over $1.25 million so far.”

Vintage Rallies currently stages four rallies a year, which Taylor figures is the right number. They’re about to put on their 19th annual New England 1000 and currently organize the Northwest Passage in the Canadian Rockies, the Texas 1000 in the Texas Hill Country and the Mountain Mille in West Virginia, which Vice President of Private Client Services Paul Schneider will be joining later this year.

Over the past 19 years, the Taylors have learned not to accept more than about 50 cars for each event. If there’s a larger number of cars — as they’ve found out more than once — start, finish and meal times become too complicated. They also find that if there are fewer entrants, they’re more likely to mix with each other and become friends instead of forming little cliques.

The Taylors have worked hard to ensure that their rally participants come from a wide cross-section of the collector car world. As a result, their guests bring a truly varied range of machinery from MGAs to 2.9 Alfas and Ferrari GTOs. Many of the participants are small business owners, although the rallies have also proven popular with doctors, lawyers and investment bankers. But what’s really made the events successful is that well over 60 percent of the entrants repeat the experience.

Those repeat guests appreciate that starting points, routes and hotels vary every year, so that someone who runs the New England 1000 two years in a row is unlikely to drive the same piece of road twice. Rich and Jean plan all the routes themselves, and Jean personally selects the hotels and restaurants. Vehicle support is provided by official mechanics Peter and Stephen Markowski from RPM VT. Transporters from RPM VT and Exotic Car Transport carrying new Porsche sports cars follow the route, and if a car fails and can’t be repaired, the entrants finish the day driving one of the new Porsches, while their car rides along.

Rich and Jean are content to remain “a mom-and-pop operation” with their four events a year. However, they’re considering a new event that may alternate with one of the existing rallies. From time to time they also put on special events for clubs, auto manufacturers or one frequent entrant who wanted an all-Duesenberg tour.

If the Taylors had any goal when they started, it was to put on a rally that was fun, luxurious and relaxing. That one “hobby” event has grown into 65 rallies over 19 years. Although the Taylors immensely have enjoyed every one of the events, they are particularly proud of the impact they’ve made on a variety of small charities over the years. Says Taylor, “It’s our way of giving back.” As they gear up for the 2011 rally season, it’s clear, though, that Rich and Jean Taylor intend to give plenty more to both their rally guests and deserving charities throughout North America. For more information go to

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