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Region · #249 of the Top 500

New England in fall

From late September to late October the hardwood hills of Vermont, New Hampshire, western Massachusetts and northwest Connecticut turn red, orange and gold, peaking first in the north and at height and working south. These challenges keep inland, to covered bridges, white churches, waterfalls and mountain-pass overlooks, and several of the roads and fee sites they use close or stop charging once the season ends.

7 challenges · 36 stops

A Bridge of Flowers and the Potholes Below crestSTARTER

A Bridge of Flowers and the Potholes Below

≈ 400 steps0.2 mi · about 1.5 hoursStarter · 2 stops · 500 credStart where you live.

A short village walk in Shelburne Falls, Massachusetts: across the old trolley bridge planted end to end with flowers, then down the street to the glacial potholes in the Deerfield River below the dam. Under half a mile on foot, about an hour and a half with time to look. The bridge is open April through October.

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Bridges of the Ottauquechee crestSTANDARD

Bridges of the Ottauquechee

≈ 3,500 steps + 10 mi by car1.6 mi on foot · about 4 hoursStandard · 5 stops · 600 credOne trip earns it.

A half-day drive along one Vermont river, from the gorge at Quechee through Taftsville and Woodstock village to West Woodstock: four covered bridges and the steel bridge over Quechee Gorge. About 12 miles by car, with short walks at each stop.

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Granite and Water in Franconia Notch crestSTANDARD

Granite and Water in Franconia Notch

≈ 3,500 steps + 15 mi by car1.6 mi on foot · about 5 hours · + the walk in to 1 stopStandard · 4 stops · 600 credOne trip earns it.

A half-day through Franconia Notch State Park in New Hampshire, driving the parkway between four stops: the Flume Gorge walk to Avalanche Falls (ticketed, open May to late October), the Basin pothole, the plaza where the Old Man of the Mountain can still be seen, and a short climb to Artist's Bluff over Echo Lake.

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Litchfield Hills by the Housatonic crestSTANDARD

Litchfield Hills by the Housatonic

34 mi by carabout 5 hoursStandard · 4 stops · 600 credOne trip earns it.

A half-day drive through northwest Connecticut: two covered bridges over the Housatonic River, a staircase of waterfalls at Kent Falls, and the white church on the green in Litchfield. About 40 miles by car. Kent Falls charges out-of-state cars a parking fee from April through October.

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Stowe and the Notch Road crestADVANCED

Stowe and the Notch Road

33 mi by carabout 7 hoursAdvanced · 6 stops · 800 credGetting there is not the hard part.

A full day by car in north-central Vermont, from Waterbury up to Stowe village and on over Route 108 to the top of Smugglers' Notch: a hillside of retired ice cream, a white steeple, a covered bridge with a ghost story, and two waterfalls. About 25 miles. Route 108 through the notch closes in winter, and big vehicles are barred from it all year.

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The Kancamagus, River to Pass crestADVANCED

The Kancamagus, River to Pass

≈ 1,500 steps + 20 mi by car0.7 mi on foot · about 7 hours · + the walk in to 1 stopAdvanced · 7 stops · 800 credGetting there is not the hard part.

A full day driving the Kancamagus Highway west from near Conway to the hairpin above Lincoln: a covered bridge, three Swift River waterfalls and gorges, then three overlooks at and beyond the 2,855-foot pass. About 30 miles; the waterfall sites charge a White Mountain National Forest day-use fee from mid-May to mid-October. There is no fuel or phone signal along the road.

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The Mohawk Trail to Old Bennington crestADVANCED

The Mohawk Trail to Old Bennington

≈ 2,500 steps + 75 mi by car1.1 mi on foot · 1 day or moreAdvanced II · 8 stops · 800 credGetting there is not the hard part.

Two days by car from the Mohawk Trail in western Massachusetts up the tallest mountain in the state and north into southern Vermont: a statue, a hairpin lookout, the Greylock summit tower, Bennington's monument and white church, and three covered bridges ending at Arlington. About 90 miles. The Greylock summit road is seasonal and closes for winter.

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Counted between stops; you'll walk more at each one.

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