You can have it both ways when you visit

A car drives down Monument Ave in Bennington on Thursday afternoon.

November 1, 2023

If you come to Bennington, you can have a wonderful stay right here without ever leaving town. Cultural attractions, recreational opportunities, shopping, eating, drinking: Bennington has it all. 

But it’s also a great base for explorations of the surrounding towns and their own attractions, along every point of the compass. You could, for example, 

Go East…

…to Woodford, home of Prospect Mountain (15 min.)

A skier heads out on one of the trails at Prospect Mountain Ski Area in Woodford on Monday afternoon. Manchester Journal photo.

30 kilometers of groomed trails (for both skating and traditional Nordic skiing styles) swoop through beautiful woods at this well-managed, non-profit cross-country ski area at a snowy elevation. Ski and snowshoe rentals available. 

…to Wilmington, a resilient mountain town (27 min.)

Photos by Phil Holland

The picturesque main street is lined with independent shops like Bartleby’s Books and Quaigh Designs, a purveyor of Scottish woolens and crafts. The State Liquor store, Ratu’s, stocks spirits from Vermont distilleries and a wide selection of Vermont brews; Ratu’s also operates a recreational cannabis outlet next door. If you’re hungry, dependably good eateries like The Anchor and 19 South Main and the newly opened Valley Craft Ales at the Old Red Mill will take care of you. As for downhill skiing, Mount Snow in West Dover (38 min. from Bennington) has trails for all abilities. 

Go North…

…to Arlington, where Norman Rockwell lived (20 min.)

Spouses and co-owners Robert and Julie Jones show off some of the authentic Scottish apparel offered for sale at Rablogan Castle of Scotland in Arlington. The Australian natives both have Scottish ancestry.

The West Mountain Inn and the Arlington Inn offer fine farm-to-table dining. Bronwyn is a new place with German specialties. If you go looking for the Cheese Shop, you won’t find it: it’s now Rablogan Castle, with Scottish clothing and organic Scottish oats to take home for perfect porridge. They stock choice Vermont cheeses, too. Rockwell’s own former premises are now a country inn called Rockwell’s Retreat, near a covered bridge, natch.

…to Manchester (31 min.) and the mountains 

Vermont Kitchen Supply is truly one of a kind for a great shopping experience.

For ski mountains, you have a choice of Bromley (34 min.) and Stratton (47 min.). The outlet stores in Manchester come and go, but you can always find something fashionable to wear, for indoors, outdoors, and (especially) the slopes. The Orvis stores are mainstays, as is the Mountain Goat on Main. For cookware, you’ll get expert advice at Vermont Kitchen Supply on lower Main. The well-stocked Northshire Bookstore also has clothes and a wonderful children’s department. 

Go South…

…to Williamstown, Mass., more than a college town (19 min.)

Photo credit: Berkshire Eagle.

The home of Williams College is also the site of the outstanding Clark Art Museum. It’s open Tuesdays through Sundays all winter, with a program of talks, tours, and films. Here’s what’s happening in November. Film-lovers from Bennington often drive down to Images Cinema to catch movies not made for the multiplex.

…to North Adams, home of MASS MoCA (28 min.)

The Beths perform at Here and There Festival held at MASS MoCA.

They built it – or converted it, to be precise – and people have been coming for more than 20 years to the Massachusetts Museum of Contemporary Art, housed in former factory buildings. The Museum puts on events, too.

Go West…

…to nearby Hoosick Falls, New York (15 min.)

Yucel Erdogan at his bar in BYTE in Hoosick Falls. Michael Albans – Bennington Banner.

Bistro 42 has well-prepared French food, Byte’s got wood-oven-fired pizza, Unihog has food, drink, and live music. The Man of Kent, with British ales on tap, is a little further west on N.Y. Route 7. 

…to Troy, N.Y., a resurgent riverside city (48 min.)

Troy too is a college town: it’s home to RPI. Some graduates hang around to work for the Warner Brothers Games studio or toil on startups in lofts in the city’s elegant old brick buildings. Eateries abound. There is energy in the walkable downtown.

Of course, you can simply stay where you are and enjoy Bennington.

Two new downtown restaurants are two good reasons why you should return for dinner. Lively Union South has burgers, seafood, beer, and more (for example, a CBD Cosmo) in the renovated Putnam Hotel complex in the center of town. It’s an offshoot of Manchester’s popular Union Underground restaurant and bar. 

Service at Niramit in Downtown Bennington. Stewart Cairns – Vermont Country

For a quieter, and more exotic, experience, there is now Niramit at the South Shire (“A Little Hotel”), which bills itself as a Royal Thai restaurant offering authentic “cuisine of Siam.” The menu pairs well with the South Shire’s elegant Victorian setting; the food and service are exceptional. The dining room accommodates only 20 diners at a time; take out is available. After dinner, it’s only a three-minute walk to the Bennington Theater, with its program of plays and other entertainments. 

The Four Chimneys Inn in Bennington, Wednesday, May 24, 2023. Stewart Cairns – Vermont News & Media

A room at one of Bennington’s inns, motels, B&Bs or Airbnbs is your base. Most are independently owned and operated, and all are good value, whatever your budget. There are good times to be had, in Bennington and beyond, wherever you lay your head for the night.

Best Western
Eddington House
Hampton Inn
Harwood Hill Motel
Knotty Pine Motel
Paradise Motor Inn
The Four Chimneys
The South Shire 

Pownal resident Phil Holland writes a monthly post for Vermont Begins Here.