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.

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.

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.

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.

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.

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.

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.

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.

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.

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.