The road less traveled

Explore Southern Vermont’s hidden gems with Backroad Discovery Tours

Backroads Discovery Tours
Beauty on the backroads of Pawlet, Vt. Photo provided by Backroad Discovery Tours

By Cherise Madigan


What makes Southern Vermont such a spectacular place?

Ask Sharon O’Connor, owner and operator of Manchester’s Backroad Discovery Tours, and she’ll show you.

“I’ve lived all over the world, traveled all over the world, and I can say that what this area offers is world class,” says O’Connor, who has led countless explorers through the Green Mountains over the past two decades.

“I want to make sure that people come away from Vermont feeling the essence of the culture and the people,” she added. “I’m trying to impart a certain feeling: a sense of relaxation, pride and nostalgia for what life could be like.”

No matter the time of year, you can find O’Connor and her husband, local author and historian Dick Smith, navigating one of their 10-passenger tour buses throughout — you guessed it — Vermont’s many backroads. And with a single glance at their TripAdvisor profile, it’s evident that the couple creates an experience to be remembered.

“Sharon not only is a great tour guide but makes you understand why Vermont is so special and how its breathtaking beauty is being preserved,” wrote one reviewer. “She is so knowledgeable about the area and its history.”

“She has a friendly and warm personality and she is very knowledgeable about the history and customs of the sites we visited,” writes another. “Sharon has a way of making the tourists interact and everyone became very comfortable … the three hours went by so quickly.”

Those rave reviews often reflect the personal touch that O’Connor and Smith give their tours, as well as the many hidden gems found along their route. For many, the excursion provides an authentic and endearing view of a region that too often is distilled into a caricature of its most well-known attractions — skiing and shopping. But in taking the backroads, travelers discover a level of nuance and character that otherwise might be overlooked.

Backroad Discovery Tours
Photo provided by Backroad Discovery Tours

Among Backroad Discovery Tours’ most popular offerings is the Southern Vermont Discovery Tour, in which O’Connor leads travelers throughout humble hamlets and scenic mountain vistas to visit historic sites, abandoned marble quarries, local artisans and more. But along the way, you’ll find much more than photo ops.

“ I know all of the people on our many stops along the way,” O’Connor explains. “I introduce my people to, say, the folks at Merck Forest or the owner of the alpaca farm. They feel like they’re discovering these places with someone who really knows the area, and because of that they get to know it on a different level, too.”

In the mornings, Smith leads Revolutionary and Civil War Tours, imparting a knowledge of the area that is academic and personal. Visiting over 25 historic sites including the Bennington Battle Monument and Hildene: The Lincoln Family Home, the historian tells tales of the Green Mountain Boys and Ethan Allen, Revolutionary victories at Fort Ticonderoga and the Battle of Bennington and Vermont’s Civil War connections.

“My husband tells the story in a very interesting way — he makes it come alive,” O’Connor said. “They get excited about the Old Bennington area, the Battle Monument, and the old First Church and cemetery. He also points out a lot of little unknown homes that have to do with the Revolutionary and Civil War periods.”

The seasonal Shires of Vermont Tour allows winter and springtime visitors to explore locales like the historic Dorset Village and picturesque Manchester in lieu of an afternoon spent skiing or shopping — though there are plenty of opportunities to snag Vermont syrup, cheeses and more along the way.

“People sign up when it’s too cold out, or they’re tired of skiing and don’t really want to shop,” O’Connor added. “They discover things they may not have otherwise seen. It’s really designed for people who only have a couple of days in the area and don’t know where to go or what to see.”

The Chiselville Bridge
The Chiselville Bridge in Sunderland, Vt. Bennington Banner File Photo

Perhaps the most visually striking is the Vermont Fall Foliage Tour, capturing the cascades of color that paint the region’s mountains and valleys starting in September. While there’s no shortage of sites to visit, O’Connor and Smith typically vary their route to present visitors with the very best of Vermont’s foliage display. And, though the duo typically focuses on more intimate groups, they also offer customizable tours with access to a 54-passenger coach bus as well as step-on service for groups passing through.

No matter what kind of group she’s leading, though, O’Connor prioritizes a personalized experience for her passengers.

“I really take a personal interest in people, and I hope that they leave feeling like they’re visiting an old friend rather than taking a big bus tour,” she concluded. “If you want to see our area of Vermont and everything that makes it so special, I hope that you’ll join us.” •

Backroad Discovery Tours
A typical view during one of the company’s tours. Photo provided by Backroad Discovery Tours

Backroad Discovery Tours

Manchester, Vt.

Cost: $35 per person, advance reservations required. Tours generally meet at 21 Bonnet St. in Manchester. (Check meeting location when making reservation.)

Available Tours

Southern Vermont Sampler Tour: Daily, mid- June through September, 1 to 4 p.m.
Vermont Fall Foliage Tour: Daily, late September through late October, 1 to 4 p.m.
Revolutionary/Civil War Tour: Daily, May through November, 9:30 to 11:45 a.m.
The Shires of Vermont Sampler Tour: Daily, May through June and November through February, 1 to 3:30 p.m.

Vermont Country magazine

Vermont Country has a hyperlocal focus on the Green Mountain lifestyle, its personalities, events, attractions and culture. The magazine appears six times a year, designed to complement the state and four-season living. VtCo magazine is a Southern Vermont publication of Vermont News & Media.

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