The Best Scenic Drives In Woodstock

By Kelley Boymer
18 Aug 2023

Woodstock, Vermont, is known for its picturesque landscapes and charming small-town atmosphere. People come to Woodstock to experience the excellent farm-to-table food, souvineer and small business shopping, hikes, skiing and more. One of the best ways to see the beautiful scenic rolling mountains, farms, and meadows of Woodstock is to take a scenic drive.

If you’re looking for scenic drives in and around Woodstock today’s post is for you. Today we will share some options that will take you through beautiful countryside, quaint villages, and stunning natural vistas.

The Best Scenic Drives In Woodstock

Quechee Gorge

You can’t come to Woodstock without venturing out of town to see Vermont’s deepest gorge. Begin your drive by heading west from Woodstock on U.S. Route 4 to Quechee Gorge. This scenic drive offers breathtaking views of Vermont’s deepest gorge, carved by the Ottauquechee River. Check out the Quechee Gorge Village for shopping and dining options including the Antique Mall for cheese samples and Vermont gifts and souvineers, Pizza Chef and the Public House for pizza and pub fare and Vermont Spirits.

Route 100

Considered one of Vermont’s most scenic roads, Route 100 offers a captivating drive through charming towns, rolling farmlands, and the Green Mountain National Forest. Heading north from Woodstock, you’ll pass through picturesque villages like Plymouth, Killington, and Warren. If you are looking for an even longer day trip, you are in luck because the Scenic Route 100 Byway is also Vermont’s longest highway running over 200 miles long and passing through many of Vermont’s quaint, small towns. Route 100 is especially spectacular during the fall when the leaves are changing to beautiful hues of red, orange and yellow.

Vermont Route 12

Take a drive south on Vermont Route 12 to explore the countryside dotted with picturesque farms and open meadows. This route passes through charming towns like Barnard, Bethel, and Randolph, offering a quintessential Vermont experience. Stop at the Barnard General Store for breakfast, lunch or ice cream and Silver Lake for a refreshing dip during the summer or a walk around the lake during the fall.

Pomfret Loop

If you are looking for a drive that brings you through classic Vermont backroads, head east from Woodstock on Pomfret Road to embark on a delightful 18-mile loop drive through the rural beauty of Pomfret. This scenic drive takes you through rolling hills, past historic farms, and along the shores of picturesque Silver Lake.

Bridgewater Corners Loop

Venture southwest from Woodstock to enjoy the Bridgewater Corners Loop. This drive offers scenic views of the Ottauquechee River, the iconic covered bridge in Bridgewater, and the charming village of Bridgewater Corners. Head to Long Trail for some freshly brewed beer and pub fare or Ramuntos Brick and Brew Pizza for some classic New York style pizza and a laid back atmosphere that is perfect for kids. For something a bit more off the beaten path, take the dirt road, North Bridgewater Road back to Route 12 and loop back to Woodstock.

Old River Road

Head north on Route 12 out of the village of Woodstock and turn right at Billings Farm and Museum onto Old River Road. Follow the dirt road along the meandering Ottauquechee River past scenic homes, farms and rolling hills. You can continue until the Taftsville Bridge and cross the bridge looping back to Woodstock or continue through until the Simon Pearce Mill in Quechee and cross the covered bridge directly after the Simon Pearce store on your right to loop back to the village of Woodstock on Route 4. Stop at Simon Pearce for views of the falls, some glassware, pottery or an up-close look at glassblowing.

Remember to check road conditions and be prepared for various weather conditions, especially during winter. These scenic drives in and around Woodstock, Vermont, will provide you with a delightful journey through the region’s natural beauty and charming countryside.

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