The Essential Guide to Route 100 in Vermont

• At 146 miles in length, Vermont’s Route 100 is the state’s longest highway, and passes through charming small towns and rolling farm land. 
• Along the route, travelers can sample maple syrup, hike scenic, wooded trails that end at waterfalls, explore museums, and warm up in charming cafés.
• There are plenty of charming stays along the way, ranging from idyllic farms to bed and breakfasts.

At 146 miles in length, Route 100 is the longest highway in Vermont—and it’s also one of the most iconic and quintessential fall drives in the Green Mountain State.

The road runs through the geographic heart of Vermont, from Massachusetts to the Canadian border, and cuts through the iconic Green Mountain range. The history of the road dates back to 1937, and it’s just one of 10 federally designated scenic byways in Vermont. However, Route 100 is truly one of the most stunning—and since billboards are banned in the state, you’ll be able to experience uninterrupted scenic beauty.

While the Scenic Route 100 Byway is also known as “The Skier’s Highway” for the epic amount of ski resorts that can be found off of it, it’s also often called “Vermont’s Main Street.” And with its charming small towns and gorgeous landscapes, it’s a popular choice for a scenic drive in the fall as well, when the leaves turn vibrant shades of yellow, orange, and red. I’ve personally visited the Green Mountain State for over two decades, and haven’t tired of it yet.

Here’s what you need to know before taking a road trip on Vermont’s Route 100.

Best Things to Do

Moss Glen Falls in Vermont.

Mark/Adobe Stock

Hike in a state park.

Enjoying a swimming hole in the summer is a prime Vermont pastime, but the state’s waterways are just as magical in the colder months. Waterfalls are an especially beautiful sight during winter—sometimes, when the weather is cold enough, the water freezes as it leaps off the rocky ledges. Thundering Brook Falls Trail in Killington is a short but worthwhile hike. Up north in Stowe, Vermont, you will find the tallest waterfall in the state at Moss Glen Falls, which towers above the forest floor at 85 feet. In Ludlow, you can wander trails in one of southeast Vermont’s largest forest parcels (aka a piece of land owned by the state), Okemo State Forest. I also recommend checking out Buttermilk Falls, which is easily reachable via a half-mile hike.

Cozy up with a book and coffee.

You can’t have a road trip without coffee, and you most certainly can’t get cozy without a good book. Located in the town of Wilmington, Vermont, visiting The Village Roost is the perfect way to begin your drive on Route 100. Here, you’ll find homey, wood beam ceilings, gift baskets, and a menu full of organic, locally sourced delights. Further north in Ludlow, you can tuck into the cutest little store, The Book Nook, for new releases and some discounted options as well. Sandy’s Books & Bakery in Rochester, Vermont, combines two great things: books and pastries.

Sample some maple syrup.

It should be illegal to step over Vermont state lines and not sample as much maple syrup as possible. According to the state’s tourism board, Vermont produces more than half the country’s supply of maple sugar, and in 2024, producers made a record 3.1 million gallons in 2024. There are more than 3,000 sugarhouses statewide, and luckily, Route 100 is packed with shops that sell everything from maple candy to giant tubs of syrup. Between Route 100 and Ludlow’s Lake Pauline is the charming red-roofed Green Mountain Sugar House. The shop is full of maple offerings, and it also sells local products and toys for the kids. North in Warren, Vermont, you will find the West Hill Sugar Orchard, which has worked the same eight acres of sugar maples since 1937.

Go back in time at a museum.

Founded in 1791, Vermont is a goldmine of historic landmarks and curiosities. In Waitsfield, Vermont, you’ll find one of the most unique museums along Route 100, the Madsonian Museum of Industrial Design, which focuses on antique cars and everyday objects, such as toasters, radios, and even golf gear. The museum also has an experimental concrete house designed by award-winning architect Dave Sellers that can be booked for stays.

If you’re a history buff, check out the President Calvin Coolidge State Historic Site in Plymouth, Vermont, which is dedicated to the birthplace, childhood home, and resting place of Calvin Coolidge, the 30th president of the United States. Make sure to stop by the gift shop before you leave for some presidential memorabilia. 

How to Plan A Trip

Street signs directing traffic to Route 100.

WoodysPhotos/Getty Images

It’s not impossible to conquer 150 miles of road in one day, but Vermont’s most scenic byway deserves to be taken in over at least a long weekend. Route 100 is home to a handful of small towns, but each one has its own unique reason for being a worthy stop. This highway is quintessentially Vermont, which means that the beauty of it lies in taking things slow and easy. Give your itinerary plenty of breathing room and downtime, so you can savor the little moments—whether it’s the snow falling outside a warm café window or tasting the unique, subtle differences of varying maple syrup grades. 

When to Go

Aerial view of a Vermont town along Route 100.

spiritofamerica/Adobe Stock

The beauty of Vermont lies in its seasons. Summer is full of farmers’ markets, swimming, and river rafting, but there’s still plenty to enjoy as the air cools and the snow begins to fall. Winter is a busy time, especially in towns with popular ski slopes like Ludlow’s Okemo Mountain Resort and Sugarbush Resort in Warren. However, Route 100 shines particularly brightest (both literally and figuratively) in the fall, when the trees lining the road light up with brilliant fall colors. Lined with scenic small towns, stunning waterfalls, and classic Vermont landscapes, you would be hard-pressed to find a more beautiful fall drive in the U.S.

Where to Stay, Eat, and Drink

A red farm and fall foliage in Rochester, Vermont.

Tom Narwid/Getty Images

Rochester

Rochester’s population hovers around 1,000 people, and while it’s a fairly small town, it punches above its weight with dining and lodging options. Liberty Hill Farm is a great pick, especially for families, and is set on a working farm. If you want to get your hands dirty, you can even help out with farm chores. After you work up an appetite, you can head to the center of town to the bustling Rochester Cafe & Country Store for lunch. Make sure to check out their gift shop for handmade self-care products, like lavender-infused lotion.

Londonderry

Seven miles east of Bromley Mountain Ski Resort is the town of Londonderry, Vermont, and its less crowded ski area, Magic Mountain Ski Area. Work up an appetite on the slopes, or take a sleigh ride that ends with hot apple cider at Taylor Farm, before hitting up the Mexican tacos at Taqueria El Chepe or visit Solo Farm & Table to enjoy a seasonal menu within an airy space with wide plank floors and wooden beams. Lastly, don’t forget to grab a souvenir bowl at Lasser Ceramics. 

Weston

In 1946, Vrest and Mildred Ellen Orton opened The Vermont Country Store in the quaint village of Weston, Vermont, and is still family-owned. Here, you’ll find everything from candy and snacks to bedding and flannel. You can also indulge in a Vermont “creemee” and milkshakes year-round at their Mildred’s Dairy Bar, and explore a menu full of comfort food at Mildred’s Table. You will find classic Vermont style and luxury at the five-room Weston at its on-site restaurant, The Left Bank. Before you hit the road, check the event calendar at the Weston Theater Company. 

Ludlow

With an array of excellent restaurants and shops, including the hip 3 Graces boutique, Ludlow is a great place to stop for at least a night. The charming Governor’s Inn Bed & Breakfast is walking distance from the quaint Ludlow village shops and restaurants, and less than a mile from Okemo Mountain Resort. While you’re in town, you can get Mexican fare at Mojo Cafe, pizza at Goodman’s American Pie, and a hearty breakfast at the homey Hatchery.

Waitsfield

After passing through Hancock, Route 100 technically ends, but keep going for a few more miles on the Mad River Byway, which is also a part of the scenic byway. End your trip in the town of Waitsfield and its quaint neighbor, Warren, where you can treat yourself to a stay at The Pitcher Inn, about eight miles away by car. Whether it’s an après-ski cocktail at Tracks Tavern, a fine dining experience at 275 Main, where chef Jacob Ennis celebrates the region’s farmers through seasonal menus, or simply reading by the fire after a day of driving, the Inn is a true winter haven. Across the cobblestone street is the Inn’s Warren Store which serves sandwiches, coffee, and incredible pastries. Families will also enjoy the American Flatbread restaurant at Lareau Farm in Waitsfield.

“It’s the original home of American Flatbread and such a special place in the Mad River Valley,” says Ennis. When he and his wife have a babysitter, they also like to head to Scrag & Roe. “It’s refined, creative, and reminds me how vibrant and diverse food can be even in our small mountain towns,” he says.