The 8 Best Vermont Road Trips

Fall Foliage Road Trip Vermont
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In Vermont, road-tripping is as exhilarating as any outdoor sport. This land of mountains, maples, covered bridges, and cows never disappoints drivers with its bending, ascending roads and rustic scenes. And if you're in the passenger seat, even better: You can scout angles for panoramic photos and keep an eye out for farm stands, funky shops, and roadside oddities like Vermontasaurus. Because cell phone service is still spotty in some parts of Vermont, it's always wise to have a game plan before you hit the road. Here are eight outings that showcase Vermont's splendid scenery and its singular way of life.

01 of 08

Vermont Route 100

Moss Glen Falls Vermont
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Just drive the Scenic Route 100 Byway—south to north or north to south—and you can travel nearly the entire length of the state. It's an easy-peasy road trip chock full of quintessential Vermont experiences. Plan to stop often at attractions like the Vermont Country Store in Weston, where the famed retailer's catalog of local wares and old-school products comes to life; photogenic Moss Glen Falls; and the Ben & Jerry's Factory and Cold Hollow Cider Mill in Waterbury. Most road trippers end their trek in Stowe, but you can continue on VT-100 all the way to Newport, not far from the Canada border. The road is only two lanes its entire 216 miles, so plan for traffic on peak fall foliage weekends and again when this becomes the "Skiers' Highway" in the winter months.

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02 of 08

The Covered Bridges of Bennington County

West Arlington Covered Bridge in Vermont
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Vermont has the densest concentration of covered bridges of any U.S. state, and with more than 100 scattered statewide, these picturesque structures could provide inspiration for many a road trip. When your time is limited and you want to collect photos of some of Vermont's prettiest covered bridges, your best bet is this scenic drive through Bennington County in the southwestern part of the state.

Before you set out, check out Bennington's top attractions, including the Bennington Museum, with its eclectic Vermont-made artifacts and Grandma Moses paintings; the gravesite of beloved New England poet Robert Frost; and the Bennington Monument, which features an observation deck with phenomenal views. Pick up sandwiches at the Elm Street Market and head north on a route that takes in five classic, red-painted "kissing" bridges. You'll wind up at one of the oldest original covered bridges in Vermont: the 1852 West Arlington Bridge. It should come as no surprise that artist Norman Rockwell once lived steps from this picture-perfect landmark.

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03 of 08

Jericho to Stowe Through Smugglers' Notch

Smugglers' Notch Road, Jeffersonville, Vermont
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Fall is an awe-inspiring time for a drive through Vermont's best-known mountain pass: Smugglers' Notch. Start your trip at the Old Red Mill in Jericho. As its name implies, this mid-19th-century mill has been a fixture on Browns River for generations. It now serves as home to the Jericho Historical Society and its museum of photos by Wilson "Snowflake" Bentley: the Vermonter who captured the first-ever images of individual snowflakes.

Start by driving east on VT-15 toward Underhill, with Vermont's highest peak, Mount Mansfield, in view. VT-15 angles north to Cambridge, then parallels the Lamoille River en route to Jeffersonville; here, you'll turn south on VT-108 for a spellbinding run through Smugglers' Notch. Twice in history, during the early 1800s and again during the Prohibition years from 1920 to 1933, this narrow passageway served as a smuggling route for illegal goods from Canada.

This is eyes-on-the-road driving and a true thrill. As you're planning your road trip, it's important to know that VT-108 is closed from mid-October through mid-May. If this is the case, continue on VT-15 until you reach VT-100; this historic route will take you the rest of the way to Stowe, one of Vermont's most iconic villages.

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04 of 08

White River Junction to Reading: A Photographer's Dream Drive

Route 4 Quechee Gorge Bridge over the Ottauquechee RIver in Vermont
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If the goal of your road trip is to capture photos of scenes that practically scream "Vermont," pick up US-4 West in White River Junction. Soon, you'll be driving right over Quechee Gorge, known as Vermont's Little Grand Canyon; park and walk out over the gorge, or hike along the Ottauquechee River's banks. Afterwards, visit the raptors at VINS, shop and dine at the Mill at Simon Pearce, and stop to photograph the Taftsville Covered Bridge en route to the architecturally rich town of Woodstock.

You could easily spend the rest of the day in Woodstock snapping pictures of Middle Covered Bridge and the classic town green, the Jersey cows at Billings Farm and Museum, the gardens and grounds of Marsh-Billings-Rockefeller National Historical Park, and even aerial views of town if you hike up Mount Tom. But how can you resist visiting Jenne Farm? New England's most-photographed farm is just south of Woodstock in Reading off VT-106. Continue south on VT-106, then travel west on VT-131 through protected woodlands, and pick up VT-100 North in Ludlow back to US-4.

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05 of 08

The Vermont Cheese Trail

Plymouth Cheese on the Vermont Cheese Trail
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Where there are cows, there's cheese! And Vermont is known not only for large, world-class producers like Cabot but also for small artisan cheesemakers. Plan a delicious road trip with the Vermont Cheese Council's handy, printable Vermont Cheese Trail map, which pinpoints the locations of cheese farms and factories that are open to the public. For the ultimate cheese trip experience, start at America's oldest cheese factory, Crowley Cheese in Mount Holly; then, make stops at Plymouth Artisan Cheese in Plymouth, Vermont Farmstead Cheese Company in Windsor, and the Cabot sampling station at Quechee General Store. Be sure to bring a cooler for all of the cheeses you'll want to bring home.

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06 of 08

Molly Stark Byway

Fall View from Fire Tower, Molly Stark State Park, Molly Stark Byway
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The perfect road trip for hikers and history lovers, the Molly Stark Byway—named for the wife of the Revolutionary War "Hero of Bennington" General John Stark—is an east-west route across the southern part of Vermont. Whether you start on the western end in Bennington or the eastern end in Brattleboro, you'll follow scenic VT-9 through a region that was once the haunt of war hero Ethan Allen, poet Robert Frost, and late-bloomer artist Grandma Moses. Along the way, you'll encounter cute villages and motor right through the Green Mountain National Forest. Don't miss the view from the deck at Hogback Mountain Country Store in Marlboro. You'll find many places to park and hike, such as Molly Stark State Park, where a trail up Mt. Olga leads to a fire tower with spectacular views.

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07 of 08

A Vermont Island Drive

Grand Isle in Lake Champlain, Vermont
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Drive US-2 West out of Burlington, Vermont's largest city, and embark on an island adventure. Route 2 travels over the islands in Lake Champlain and the bridges that connect them, and is particularly enjoyable in the summer. Sample wines at Snow Farm Vineyard on South Hero Island (also known as Grand Isle) and dine lakeside at North Hero House on North Hero Island. On Isle Lamotte, Fisk Quarry Preserve and Goodsell Ridge Preserve are fascinating places to hike and to see the oldest known coral fossils. When you reach the town of Alburgh—located on a peninsula that juts down from Canada into Lake Champlain—head for Alburgh Dunes State Park and take a dip in the refreshing waters of what has often been called the sixth Great Lake.

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08 of 08

The Northeast Kingdom

Lake Willoughby in Vermont
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Wild and remote, Vermont's Northeast Kingdom is a gorgeous place to drive up mountains and along lake shores. Start your journey at Dog Mountain in St. Johnsbury, where you are free to roam and to appreciate the artful legacy of Stephen Huneck. From here, pick up US-2 East to VT-114 North. Watch for a right turn onto the toll road that leads to the summit of Burke Mountain, where you'll find a fire tower to climb: the views will wow you. Descend and retrace VT-114 south to Lyndon, where you'll connect to US-5 North. When US-5 turns left, continue onto VT-5A and trace the shore of Lake Willoughby, flanked by Mounts Pisgah and Hor. The beauty of this crystal-clear pool will mesmerize you; there are beaches at both the southern and northern edges of the lake.

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