The Green Mountains

Vermont’s rolling hills offer culture, country charm, cheese, and much more

Let’s get one thing straight up front: The Green Mountains are synonymous with Vermont. Perhaps it’s because the rolling green hills extend all the way from the state’s southern border with Massachusetts to the Canadian province of Quebec. Not as high or as craggy as the Adirondacks to the west, or New Hampshire’s White Mountains to the east, the Green Mountains are a popular four-season playground and offer the best skiing in the East. Combine this with the funky and fiercely independent spirit that permeates this small and mostly rural state, and it’s no wonder that come leaf-peeping season, picturesque back-country roads are bustling with visitors exploring the quaint towns (with their village squares), the covered bridges (more than 100), the many farms (cheese, please!), and the endless outdoor opportunities.

Some say French explorer Samuel De Champlain first dubbed the mountains Les Verts Monts (that’s French for Green Mountains) in 1609. Ever since then, Vermont has been doing things its own way. In fact, for 14 years Vermont functioned as its own republic, even using its own currency before ultimately becoming the 14th state in 1791. In the ’60s and ’70s, an influx of disaffected young people, better known as hippies, moved to communes in rural Vermont, and they’re widely credited with transforming the region into one of the country’s most liberal states.

A 306-foot obelisk commemorates the Battle of Bennington

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It’s easy to traverse the state. Route 100 runs the entire length of the Green Mountains, as does the 273-mile Long Trail, which is the oldest long-distance trail in the country and was the inspiration for the Appalachian Trail. (The two routes overlap for 100 miles in the southern Green Mountains.)

With hundreds of art galleries and dozens of small theater companies, there is plenty of culture to keep you busy, too. The world-class Bennington Museum, which underwent a major renovation last year, houses the world’s largest public collection of Grandma Moses paintings, as well as a permanent Bennington Modernism gallery. Tourists there also enjoy the summer home and grave of poet Robert Frost and the short elevator trip up the 306-foot obelisk at the Bennington Battle Monument. In Woodstock, the Billings Farm & Museum offers a unique and interactive way to see a working farm, as well as to learn about Vermont’s farming heritage. (Vermont has the largest number of cows per person in the country.) Hop on the Vermont Cheese Trail and visit several cheese farms in one afternoon. The sharp cheddar is legendary, but award-winning artisanal Gouda, feta, and other varieties are also being churned out these days. With its over-the-top fun (think tie-dye and the “flavor graveyard” out back), Ben & Jerry’s Ice Cream Factory in Waterbury offers a one-of-a-kind 30-minute tour.


  • Distance from Poughkeepsie: 2 hours and 45 minutes to Brattleboro, 4 hours to Burlington in the north
  • Population: 626,562 (as of 2014)
  • Highest peak: Mount Mansfield (4,393 ft) in Stowe; the summit is accessible by a historic gravel toll road
  • Best known for: maple syrup (the largest producer in the country), ski resorts, Ben & Jerry’s, verdant green vistas


Smuggler’s Notch Resort

4323 Rte. 108 S, Smuggler’s Notch, Vermont
Rates begin at $156/night

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A popular ski resort that services three different mountains, the sprawling Smuggler’s Notch is a family-friendly find any time of year. Five different condo communities offer lodging opportunities ranging from studios to five-bedroom lodging options; all come with cable TV and kitchens. While the pools and water slides shut down in autumn, the highly touted zip-line tours, as well as the 2.5-hour treetop obstacle course, remain open in the fall. Now in its third year, the Autumn Walking Experience continues to attract new devotees. Choose from the apple walk, a waterfall walk, a mushroom-hunting jaunt, or more than eight other fully guided, small-group tours. Other resort programs include outdoor yoga, art classes, and trips to nearby attractions including local breweries, apple orchards, and even Montreal (a two-hour drive).

dorset inn
The historic Dorset Inn has 25 updated rooms

The Dorset Inn

8 Church St. & Rte. 30, Dorset, Vermont
Rates begin at $165/night

The oldest continually operating inn in the state opened its doors in 1796. Sure, the floors creak, but this gem just oozes with old-fashioned charm without spilling over into kitschy territory. The 25 comfortable guest rooms and suites are enhanced with flat-screen TVs, as well as whimsical touches. Sit by a pretty fireplace, indulge in a burger in the tavern (smothered with their famed bourbon ketchup), pamper yourself in the day spa, or walk across the green to explore the Dorset Union Store.

Twin Farms

452 Royalton Tpke., Barnard, Vermont
Rates begin at $1,450/night

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Situated on 300 acres of lush meadowlands, this all-inclusive retreat — the only five-star resort in the state — is known for outstanding service, and even better food. There are no menus here, but guests are welcome to join the chef as he gathers seasonal ingredients from the property and transforms them into memorable meals. The original 1795-era farmhouse has been converted into common rooms, and the ten luxurious guest cottages are all unique; some even feature artwork by the likes of Roy Lichtenstein. Ride a bicycle, hike through the whimsical gardens, or enjoy a spa treatment. The best place to check out the changing leaves? In the Fuor, a 104-degree Japanese-style soaking tub.

vermont wine and harvest festival

The Vermont Wine & Harvest Festival is a three-day celebration of the bounty of the Green Mountain State. The fun kicks off on Friday night, with the not-to-be-missed Village Stroll and the fiercely competitive Soup Tasting Contest. The festival runs from September 18 to September 20.


In the higher elevations of central and northern Vermont, the foliage typically peaks the last week of September. Areas of lower elevation, as well as southern Vermont, display their greatest brilliance in mid-October. And we are talking about brilliant: Vermont has the highest concentration of red maple trees in the country, and the ensuing foliage is stunning. The Scenic Route 100 Byway, a rambling 138-mile stretch of road that connects 20 towns in South-Central Vermont, is internationally known as one of New England’s most breathtaking drives. Riding the Green Mountain Railroad ( or taking a cable car to the top of a mountain are two other quintessentially Vermont ways to ooh and aah at nature’s glory.

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