Breakfast at Four Chimneys Inn. Photo by Mindy Briar

November 1, 2021

People who live in Bennington miss out on half the fun. The other half is reserved for those who visit the town and stay overnight – or perhaps several nights – in Bennington’s independently owned inns and motels. 

Veteran hotelier Joseph Polito bought the South Shire Inn six months ago after a national search for the right property to own and manage.

He found what he was looking for in the 1887 former home of local banker Luther Graves, a Bed and Breakfast since the 1970s, with nine well-appointed rooms and an attractive, wood-paneled common area, a short walk from the center of town.

South Shire Inn

The architecture is Victorian, but there are no doilies in the lounge, where a volume of poems by Robert Frost lies on the table and chessmen face off in a corner. The kitchen turns out a full Vermont breakfast to start guests on their day.

Polito was drawn to the area, he says, because of its many assets for visitors. “Hiking, cycling, theater right downtown, the Bennington Museum, Bennington College, Hildene, the Clark, skiing, dining, drinking, shops. It’s a pleasure to tell guests about the wonderful things we have for them here.”

The Inn’s guests come from all over, including, recently, Arizona, North Carolina, and Ohio as well as New York, New Jersey, Connecticut, and Massachusetts. The town’s residents may not feel it as they go about their daily lives, but Bennington is a destination.

Travelers have been getting the message. The last five months have been some of the busiest local innkeepers have known. The combination of Vermont’s nation-leading record on Covid vaccination, the pent-up desire for travel, and the safety of traveling by car have been filling accommodations during summer and fall, after a tough year for the lodging sector.

The prospects for the winter season look good, too. Word has gotten around that Vermont is a fun, safe getaway for a weekend or a week – and in Bennington we like to say, “Vermont Begins Here.”

“How about this for a new safety idea: you can drive your car right up to your room!” says Betsy Bluto, manager and co-owner of the Knotty Pine Motel, with a smile. “It’s as if motels had been designed for a pandemic.” The Knotty Pine, which opened in 1948 on what was then the outskirts of town but is now a commercial district, has been in Bluto’s family for almost 50 years.

bennington hotel pool knotty pine
Knotty Pine in the summer

It’s gone through numerous upgrades, but at least one wall in each room retains the original post-war pine. In a nod to current fashion (think TOURISTS in North Adams), the Knotty Pine has begun to describe itself as “modern retro” on its website. Trends aside, the fundamental things apply: clean, comfortable, affordable rooms, good wi-fi, a friendly and experienced welcome, a nice pool, a place to do laundry, and a very short walk to the car. 

Another long-established motel perched on a hill on Route 7A just north of Bennington is the Harwood Hill. Step inside the office and you’ll find yourself in a small art gallery. Paintings, pottery, and sculpture by accomplished local artists, complete with price tags, are on view. What’s more, each of the 21 rooms is also decorated with original artworks that are available for purchase.

Art on display at the Harwood Hill

This is “hotel art” with a difference, the brainchild of the former partner of the current owner, Martha Wiles. And yes, some guests do decide to purchase the art right off the walls. In any case, they get a comfortable stay with a nice view of the Bennington Monument and an apple orchard right across the road. 

The Four Chimneys Inn in beautiful Old Bennington began as a private residence in 1913 but found its true calling later in the century as a classic Vermont country inn.

Four Chimneys Inn in Bennington, Vermont by Mindy Briar.
Four Chimneys Inn. Photo by: Mindy Briar

The light-filled rooms have modern amenities, and as is the case at most inns, each room has its own distinct personality, expressed in its shape, furnishings, and décor.

Lynn and Pete Green, owners since 2005, make it easy for guests to imagine what a stay might be like; look up the Inn on Instagram and you may get hooked on the pictures. “Lots of guests, especially younger couples, follow us on social media,” says Lynn. “When guests arrive and settle in, we try to take the pulse of what they’d like from us. Some want suggestions as to what to see and do, others just want a place to relax with a cocktail by the fire, perhaps after a day of cross-country skiing at Prospect.”

Lynn calls November “the quiet season.” Guests from the megalopolis particularly appreciate the restorative peace and quiet of this time of year, she says. 

Three other independent establishments also beckon travelers.

The Paradise Inn has 70 rooms a five-minute walk from downtown (just two from the Bennington Museum). The landscaped pool, balconies with views, and the four new pickleball courts make the premises one-of-a-kind. 

Two smaller inns, the Safford Mills Inn on East Main and Eddington House in North Bennington, offer only four and three rooms, respectively, but each room is unique.

What all of the independent hostelries of Bennington have in common are knowledgeable hosts dedicated to providing a safe and pleasant stay for their guests.

Come for a visit and see for yourself…

Vermont Begins Here offers a full listing of lodging and accommodations in Bennington, Vermont, including motels, hotels, inns, and bed & breakfasts.

Phil Holland tackles subjects of local interest and was the lead writer for the Bennington Community Theater’s recent presentation of “Voices from the Grave.

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Save the Date!

During the first two weekends of December, prospective guests have an opportunity to tour a variety of inns in the Shires (as Bennington County is also known). The Shires Holiday Inn Tours run on two successive Saturdays (the 4th and the 11th) from noon to 4 p.m. Proceeds benefit local food banks. 

Booking advice from Four Chimneys innkeeper Lynn Green: Call directly for the best rates and availability. Try booking the week before or after a big holiday if you want the best deal.

Fun fact: Bennington is a popular stopover for travelers from Ohio and Pennsylvania on their way to the coast of Maine. They take the route through Bennington to keep life interesting. Some will have breakfast at the Blue Benn. Some might look up the grave of an ancestor in the Old Bennington Cemetery. And people still come for a look the Bennington Monument, one of the finest obelisks on the planet and the most visited historic site in Vermont.