There are faster ways to get from one end of Vermont to the other than via Route 100, but none are prettier or offer more interesting things to do.
Meandering for more than 200 miles over rolling hills, past forests and farms, and to some of the northeast’s best ski areas, Route 100 starts in the small town of Stamford just across the Massachusetts state line. The road traces the eastern edge of the Green Mountains as it heads (mostly) north to Newport and the shore of Lake Memphremagog, a deep glacial lake shared with Quebec, Canada. Most attractions around Stamford are actually in nearby Massachusetts; the town is just a 10-minute drive from North Adams, home to MASS MoCA and Natural Bridge State Park.
But first, Route 100 heads south and east toward Readsboro, crossing the Deerfield River and turning north in Jacksonville. The road passes through the heart of downtown Wilmington, a quintessential New England village full of white steepled churches, fine brick commercial buildings, and restaurants such as Jezebel’s Eatery, which serves farm-fresh comfort food (you can’t go wrong with a grilled cheese made with Vermont cheddar) in a historic building.
From ski resorts to general stores and an ice cream flavor “graveyard,” here are our favorite stops along Vermont’s “Main Street.”
1. Mount Snow
In West Dover you’ll find Mount Snow, the first of at least a dozen downhill and cross-country ski areas located near Route 100. In addition to 600 skiable acres in winter, Mount Snow is a popular summer destination for mountain bikers. Country bed and breakfasts dot Vermont, and one of the loveliest is the Deerhill Inn. Just minutes from the mountain, the inn serves an extensive homemade breakfast to guests. It has rooms with gas fireplaces and an outdoor pool for summer swims with mountain views.
2. Jamaica State Park
Located on a bend in the West River, Jamaica State Park has 772 acres of history and opportunities for adventure. Hikers can follow the bed of an old narrow-gauge railroad, and Salmon Hole is a popular place to cool off in the summer. If you time your visit with a spring or fall water release from the Ball Mountain Dam, you can raft through Class II, III, and IV rapids on the river. The park’s campground has both tent and lean-to sites close to the swimming hole.
3. Magic Mountain
Magic Mountain in Londonderry is an old school New England ski hill, with narrow trails, vintage chairlifts, and a laid-back atmosphere. When the white stuff melts away, the mountain has one of the best disc golf courses in Vermont and regularly hosts live musicians at the Black Line Tavern.
4. Vermont Country Store
Envious friends following along on your Route 100 adventure will be expecting maple syrup or other Vermont swag when you get back, so be sure to pop into the Vermont Country Store in Weston, which has been selling everything from penny candy to locally made clothing, kitchen goods, and housewares since 1946.
5. Okemo Mountain Resort
Continuing north to Ludlow, Okemo Mountain Resort has the biggest vertical drop of any Vermont ski area and convenient slope-side lodging at the Jackson Gore Inn. The resort also features a bike park, mountain coaster, and challenge course, making Okemo a popular year-round destination.
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6. President Calvin Coolidge State Historic Site
Located in Plymouth Notch is the birthplace of Calvin Coolidge, the 30th president of the United States. It’s worth a stop at the President Calvin Coolidge State Historic Site to stroll around the beautifully preserved village where the Coolidges lived, including the family home and parlor where “Laconic Cal” took his oath of office. Nearby Coolidge State Park is a favorite for campers thanks to its hillside campsites with views of the Black River Valley and the Green Mountains.
7. Long Trail Brewing Co.
When Route 100 forks with 100A, take the road less traveled (bear right) onto 100A, a short detour to Brightwater Corners at the intersection of Route 4. Try the Hit the Trail Ale at Long Trail Brewing Co., the king of Vermont microbrews. In addition to more than two dozen varieties of beer brewed on-site, Long Trail offers tours, a store selling beer to-go and branded merchandise, and a pub with excellent food and outdoor dining on a deck overlooking the Ottauquechee River.
8. Killington Mountain Resort
Head west on Route 4 for about 10 minutes to reconnect to Route 100, which continues north to Killington, home to the Killington Mountain Resort and Pico ski areas. Known as the “Beast of the East,” Killington is the largest ski area in the northeast, and its Wobbly Barn was named one of the “Top 5 Best Apres Ski-Bars” by USA Today. In addition to a top mountain biking park, the Killington area has several great hikes, including the 1.9-mile Deer Leap Overlook trail. The overlook offers gorgeous views of Pico Peak and the Green Mountains, especially when the foliage is changing colors in the fall.
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River tubing is the local cottage industry in Pittsfield, with Vermont River Tubing and several other operators offering summer float trips on the White River.
9. Mad River Glen
Warren’s claim to fame is the Sugarbush ski area and the 273-mile Long Trail. The oldest long-distance hiking trail in the U.S., it runs the length of Vermont, from Massachusetts to Canada. Route 100 serves as the main street of Waitsfield, where the Mad River Glen ski area challenges skiers (but not snowboarders, they are banned) with some of the toughest trails and snow conditions in New England. If you want to linger, the Inn at the Round Barn Farm is an upscale B&B surrounded by organic gardens and its own hiking and snowshoeing trails.
10. Cold Hollow Cider Mill
For a literal taste of Vermont, make a stop at the Cold Hollow Cider Mill in Waterbury Center, where you can sip on fresh-pressed apple cider, munch on a cider donut, and stock up on Vermont maple syrup. A little further north up Route 100 is the Cabot Farmer’s Store, which not only offers tastings and sales of Cabot cheeses you might not find back home, but also carries local beer and wine and has a Smugglers Notch Distillery tasting room.
11. Ben & Jerry’s Factory Tour
The final leg of Waterbury Center’s tasty attractions is the Ben & Jerry’s Factory Tour and Ice Cream Shop, a summer tourist magnet where visitors can learn how ice cream is made, sample current flavors, and visit a “graveyard” where retired flavors are laid to rest.
12. Stowe Mountain Lodge
A few more hilly twists and turns on Route 100 will bring you to Stowe, the best all-around ski town in New England, no matter the season. Some of Stowe’s shops and restaurants line Route 100, but you’ll need to head west up Route 108 to explore the rest of the village and reach the Stowe Mountain Lodge. The town has lodging for nearly any budget, from modest hotels and motels alongside the Stowe Recreation Path, to upscale spa resorts like Topnotch Resort, Stoweflake Mountain Resort, and Lodge at Spruce Peak, which connects via gondola directly to the Mount Mansfield ski trails.
13. Trapp Family Lodge
German beers and Alpine-inspired cuisine are on the menu at the Trapp Family Lodge’s Bierhall. It’s just one of the many attractions (in addition to cross-country skiing, maple sugaring tours, sleigh rides, and more) offered at the resort run by the famous Sound of Music family. In town, among the many dining options are the Butler’s Pantry for breakfast and The Bench, specializing in craft beer and locally-sourced comfort food.
14. Jay Peak Resort
Westfield is the turnoff for Jay Peak Resort, the northernmost ski resort in Vermont known for its indoor water park and late-season skiing. Nearing its northern terminus, Route 100 runs east toward Newport, which has a historic downtown on the south shore of Lake Memphremagog, lake tours by boat, and a wide variety of hiking, biking, snowmobiling, ATV, and cross-country ski trails. Wave hello to Canada and celebrate reaching the end of the road with a beer and an order of poutine on the lakefront deck of the East Side Restaurant and Pub.