Vermont doesn’t offer much variety in its towns and landscape. But that’s okay because every square inch of this state is addictively charming. The largest city, Burlington, only has 40,000 people, and most towns here are actually villages dating back to the colonial period. Vermont is a place to drop out and slip back to a more pastoral era. Sleep at a historic inn in Middlebury, enjoy the fall colors in Woodstock, and get in some turns at a ski resort like Stowe or Killington. The seamless fusion of nature, outdoor recreation, and history is a powerful attraction.


One can easily argue that Stowe is the quintessential Vermont ski village. Since the ski hill is a few miles out of town, this place has its own identity apart from the slopes. The historic downtown center is postcard cute, with a lovely church on the green and a main street lined with alluring shops and cafés. Stowe attracts a more affluent crowd than other ski towns in the region and has plenty going on besides skiing. Vermont’s highest mountain, Mansfield, is nearby and there always seems to be something cultural happening in town during summer, fall, and winter. Address: Central Vermont Phone: n/a Website:


In Vermont, the vibrant university town of Burlington is what passes for a big city (it has 40,000 permanent residents). It is a refreshingly calm place, sitting on the shore of Lake Champlain with the Green Mountains at its back. Burlington has long been associated with counter culture and urban escapism. Star names like Ben and Jerry’s and Phish both hail from here, and its pedestrian mall on Church Street exemplifies what this town is about. Walking or biking is preferred to driving. There’s a healthy dose of folk culture in the Shelburne Museum and fun leisure cruises on the lake between Vermont and New York. Address: Northern Vermont Phone: n/a Website:

Northeast Kingdom

To really step back in time, take a few days and drive around the remote, insulated region of Vermont known as the Northeast Kingdom. It’s an absolutely gorgeous place, where rolling meadows crash into dense hardwood forests and little inns sprout up every now and then offering shelter. St Johnsbury is the big town here, with a handful of worthy attractions like the Fairbanks Museum. The mix of uncrowded outdoor recreation in spits like Jay Peak and Mount Pigsah is the perfect complement to bucolic villages like Craftsbury Common. Few other parts of New England are so well-designed for road tripping. Address: Northeastern Vermont Phone: n/a Website:

Mad River Valley

One of best little secrets in Vermont is Mad River Valley, a collection of farms, ski resorts, and historic villages that have managed to develop themselves into lovely tourist destinations without losing their original charm. Waitsfield and Warren are the two towns in this valley, looking much as they did during the Revolutionary War era. Two of Vermont’s best ski resorts are in the area: Sugarbush and Mad River Glen. The development around these ski hills is where the charm starts to deteriorate a bit, but it hardly affects the overall beauty of this timeless farming valley. Address: Northern Vermont Phone: n/a Website:


One of the real gems of Vermont is Middlebury. It manages to combine the sophistication of a fine college with small town charm and convenient access to superb outdoor recreation. More than 300 of the buildings downtown enjoy heritage status and Otter Creek tumbles right through the heart of Middlebury with a jovial waterfall. Breach the edge of the compact historic core and the scene reverts immediately back to empty rolling farmland and the towering Green Mountains. Several excellent historic inns are here to ensure your weekend layover is as perfect as possible. Address: Central Vermont Phone: n/a Website:


Southwest Vermont is where the heaviest dose of Americana is concentrated. Home to names like Ethan Allen, Norman Rockwell, and Robert Frost, the landscape is a continual series of large, gentle valleys cut by the inevitable river or stream. Bennington is the main town around here (and Vermont’s third-largest) and home to a respected liberal arts college as well as the site of the 1777 Battle of Bennington. Downtown is the modern face of town, with unremarkable but inviting amenities, while the historic district feels like a neighborhood plucked from colonial times. Often overlooked as a travel destination, Bennington makes a fine base for exploring this corner of Vermont Address: Southwestern Vermont Phone: n/a Website:


There were no rock festivals here – that was in New York. Vermont’s Woodstock defines the genteel side of this state’s many villages thanks in part to the attention lavished on it by the Rockefeller family. The 1765 village green, surrounded by 19th-century homes and peppered with the kind of homey businesses you’d expect to find, is simply magical. Quiet walks through the woods are just minutes from the town center, and when fall hits, this place explodes into a riot a color. Most of Woodstock is listed on the historic register, with the gentle Ottaquechee River flowing through and Mount Tom rising on the fringe. Address: Central Vermont Phone: n/a Website: n/a

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