6 Most Scenic Drives in Vermont
In Vermont, a scenic drive might start near Stowe’s covered bridges and end high on Mount Equinox, with the road doing as much of the work as the stops along it. Farther south, places like Brattleboro and Bennington show another side of the experience, where river views and old downtown blocks feel as rooted in the landscape as the scenery itself. Here are some of the best roads for seeing Vermont that way, whether you have a day, a weekend, or more.
Route 100
We start with one of Vermont’s best-known scenic highways, stretching more than 200 miles from south to north across the state. Starting in Newport, near the Canadian border, and ending at the border with Massachusetts, the thoroughfare is the quintessential road trip for leaf peeping during the autumn months, when the trees are ablaze in color.
If you're crossing over from Vermont’s southern neighbor, Massachusetts, you’ll land yourself in Stamford, a quiet locale at the base of the Green Mountains with winding, tree-lined roads that set the tone for the drive. About 25 miles north is Wilmington, a ski lover’s paradise after old man winter has rolled in. Another 25 miles further, side by side with the West River, is Jamaica State Park, a great stop for a dip in the swimming hole or a hike following an old, unused railroad track from a bygone era. Those who want more slopes should make a stop at Londonderry, home of the Magic Mountain Ski Area. Caught there in the summertime? Never fear, Lowell Lake State Park is great for small boating and other recreational activities in its natural landscapes. A drive through Route 100 also brings you to Stowe, a classic New England town with covered bridges, church steeples, and local cider, alongside more contemporary visitor amenities.
Mad River Byway
Clocking in at 36.5 miles, this byway makes a rewarding drive in any season. The journey begins in Middlesex Village on Route 2, leading south to Moretown on Route 100B, then becoming Route 100 proper once driving into Waitsfield. Continuing through the towns of Warren and Granville, you finally turn onto Route 17 before finishing at the top of Appalachian Gap.
The byway passes rustic architecture, working farms, and small-town scenery that reflects Vermont’s long history. During warmer weather, you can don your swimsuit and cool off in the many waterfalls or the Moretown Gorge swimming hole. As always, skiers will be happy as a clam due to Sugarbush ski resort and Mad River Glen, which can be found on the Byway.
Molly Stark Byway
Crisscrossing the southern tail end of the state, the Molly Stark Byway connects the towns of Bennington near Vermont’s western New York border with eastern Brattleboro bordering New Hampshire. Formally registered as Route 9, the Byway is named after the wife of John Stark, a general of a Colonial militia who returned to New Hampshire after the Battle of Bennington via the historic route amidst the Revolutionary War.
There you'll experience 48 miles through scenic lowland valleys through the Green Mountain National Forest. Brattleboro itself offers a lively downtown with art galleries, restaurants, and theaters. Driving along, you’ll be able to make a steep climb up Hogback Mountain, a stunning view spanning 100 miles encompassing Massachusetts, Vermont, and New Hampshire. Finally, finish your ride in Bennington and soak in the rich history, commemorated by the Bennington Battle Monument, which marks the decisive American victory in 1777.
The Shires of Vermont Byway
Located on Historic Route 7A and traversing past 15 villages and small towns, the Shires of Vermont Byway winds its way between the Taconic and Green Mountains, offering magnificent views from your car seat of the mountain ranges on top of the abundant waterways that supply the region.
A south-north thoroughfare, the Byway starts at the very southern end of the state until reaching Manchester, with plenty of attractions on the drive. An early stop is Bennington, as noted above, an area rich with stories from the past. One such spot is the Park-McCullough Historic Governor’s Mansion, an impeccably preserved Victorian mansion providing self-guided tours. Just up the road is the Robert Frost Stone House Museum at Bennington College, a historic home exhibiting the work and life of the celebrated poet. If you’re jonesing for a more natural setting, then keep driving almost 7 miles more to reach Lake Shaftsbury State Park for a swim in the lake or a canoe trip. Still in an aquatic mood? End your travels at the American Museum of Fly Fishing and spend the day learning about the history of the pastime sport in addition to art inspired by it.
Mount Equinox Skyline Drive
Conveniently situated on Historic Route 7A between Manchester and Arlington, the Skyline Drive fully lives up to its name. Completed in 1947, the Drive ascends 5.2 miles and rewards you with a spectacular panoramic view from the summit of Mount Equinox atop the Taconic Range.
Bear in mind, however, that the Drive is open only from Memorial Day weekend through October 31, from 9 AM to 5 PM, weather permitting. Also, the Drive is a toll road with varying prices. Memorial Day weekend through September 30, the cost for a car and driver is $25; additional passengers cost $5 each. Motorcycles are $20, and an additional rider is also $5. Children under 10 years, though, are free. From October 1 to October 31, the cost for cars and motorcycles increases to $30 and $25, respectively, with additional passengers and riders remaining at $5. Make sure to get there fairly on time; the last vehicle to be admitted is at 4 PM, while the Welcome Center closes at 5 PM.
Connecticut River Byway
Rounding out our list is a long Vermont drive that follows the Connecticut River corridor from the Canadian border south to Massachusetts, tracing the New Hampshire line. Lasting a whopping 500 miles through multiple designated routes, including Vermont Route 102 and U.S. Route 5, the Connecticut River Byway is the best way to enjoy the majestic river of its namesake on the open road. Driving up or down the Byway, you’ll also be greeted by pastoral farms and step-like terraces that have long made up the Connecticut River Valley.
If you’re coming from Massachusetts northward, consider stopping in Brattleboro for the Vermont Jazz Center, an intimate venue for musical performances specific to the genre. Upon reaching Norwich, it might be a good idea to park the car and stretch your legs on the Appalachian Trail if you’re in the mood for hiking. Driving another 55 miles will take you to Saint Johnsbury, a charming New England town perfect for exploring on foot. The Saint Johnsbury Athenaeum is a superb spot for culturalists to enjoy good reading or the many paintings in its gallery.
A Vermont Road Trip for Every Season
Pack up your skis, hiking boots, or reading glasses; Vermont is sure to not disappoint. Whether it's lush landscapes in the summer, awe-inspiring foliage in the fall, or winter sports when the land turns frost white, each season has something waiting for your wheels to skim through. You’ll be busy year-round.
