Plan Ahead for the Best of Fall in Vermont!

Jackson House Inn, Woodstock Vermont

Vermont in the fall is nothing short of spectacular, especially when you visit a town as charming and beloved as Woodstock. From enjoying scenic drives in Vermont and hiking to stunning views to savoring delicious meals and getting to know local artisans, there are endless things to do in Woodstock, VT (and the state as a whole) in the fall. 

Known as Vermont’s most scenic village, Woodstock is an unforgettable place to spend a few days. To enjoy a getaway to Vermont in the fall, you need to plan well in advance. It’s one of the most popular places to visit in New England during September and October. Couples come from all over the country to enjoy relaxed, scenic drives in Vermont, hike, bike and otherwise admire the colorful glow of Vermont’s fall foliage. 

As much as there is plenty to love about Vermont in the fall, you don’t have to go too far to enjoy it – at least when you choose lodging at The Jackson House Inn, rated as one of the best Woodstock, VT hotels. Here, we’ve curated a private, upscale oasis just outside downtown Woodstock, complete with just about everything you need for an exquisite getaway to Vermont. We offer upscale, elegant accommodations with fine art and antiques throughout the hotel and several acres of manicured gardens and scenic grounds to enjoy, all positively alight with color, just as you’d expect of Vermont in the fall. 

The simple elegance of the Jackson House Inn is not to be missed. Book your room today and ensure a chance to enjoy one of the finest Woodstock, VT hotels this fall!

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Car enjoying a drive through red foliage on one of the best scenic drives in Vermont

The Best Scenic Drives in Vermont

There’s no shortage of stunning scenic drives in Vermont – including several right here in the Woodstock Area. Route 100, considered one of the most iconic and scenic drives in Vermont, is found just a little to the west of Woodstock, VT. 

There, you’ll enjoy a breathtaking drive through tunnels of vibrant foliage, passing by the rolling hills of rural farmland and the vibrant peaks of the Green Mountains. Heading north on Route 100 from Woodstock will also take you through plenty of picturesque towns, such as Plymouth, Killington, Stockbridge, and Warren. 

We could dedicate an entire article to the joys you’ll discover along this scenic drive in Vermont, but a few highlights worth mentioning along a portion of scenic Route 100 include Plymouth Artisan Cheese, Coolidge State Park, Killington Ski Resort, and so much more. 

Route 100 is just one of the many scenic drives in Vermont worth taking, particularly in the Woodstock area. If you’re looking for other gorgeous scenic drives in Vermont this fall, consider one of the following: 

  1. Head east on Route 4 towards the Quechee Gorge. The drive offers stunning views of the Gorge, which is the deepest in Vermont. Also, it gives you a chance to enjoy this charming town, including lunch at the Simon Pearce Restaurant overlooking the river and the glassblowing studio!
  2. Head north out of Woodstock on Route 12 to Pomfret Road, and you’ll enjoy one of the most charming and scenic drives in Vermont. The loop is just 18 miles long and takes you past scenic farms with historic barns, including the popular Sleepy Hollow Farm, and plenty of rural Vermont beauty. Another highlight here, apart from the foliage, is Silver Lake.
  3. Continue north on Route 12, and you’ll come across more stunning scenery and charming communities like Barnard, Bethel, and Randolph. Don’t miss a stop at the Barnard General Store
  4. You could also head west on Route 4 out of Woodstock towards Bridgewater and Bridgewater Corners. Here, you’ll enjoy beautiful views of the Ottauquechee River. This is also a great time to visit the Long Trail Brewery
  5. Finally, head south out of Woodstock onto Route 106 toward Jenne Farm. It’s another of the most scenic drives in Vermont, offering an idyllic and picture-perfect rural scene in the fall. 

As with everything you do in Vermont in the fall, be mindful of traffic and private property, and photograph respectfully. In recent years, the onslaught of social media attention and tourists to the area – especially places like Sleepy Hollow and Jenne Farms – has made it challenging for locals and residents, and we don’t want to add to that. 

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A beautiful old barn with fall foliage - a picture of the best of Vermont in the fall

More Ways to Enjoy Vermont in the Fall

Few things beat scenic drives in Vermont in the Fall, especially when the warmth of the sun shines on our already beautiful landscapes. Vermont in the Fall, though, is a true feast for all your senses. There’s a visual feast of foliage to admire, of course, but plenty of delicious things to taste and smell, too, not to mention an intangible charge to the air that’s impossible to deny. 

Make Woodstock your base this Fall, and enjoy a plethora of scenic charm around every bend. To make the most of your trip to Vermont in the Fall, we recommend you plan well in advance to secure your reservations and ensure you are able to carve out the itinerary you desire. Apart from enjoying scenic drives in Vermont, we’ve compiled a list of even more great ways to enjoy Vermont in the Fall. 

  1. Apart from scenic drives, hiking is the best way to witness the breathtaking beauty of Vermont fall foliage. Hike to peaks on trails like the 4.2-mile Pogue/Mt. Tom loop or beautiful Mount Peg, and you’ll enjoy bird’ s-eye views of charming towns and vibrant foliage as far as the eye can see. Saskadena Six is another fantastic place to enjoy hiking or mountain biking, coupled with impressive views of Vermont in the Fall from the top of this local ski hill. 
  2. If you enjoy the drive to the Quechee Gorge, don’t miss a walk through the treetops at the Vermont Institute of Natural Science.
  3. How about a charming fall picnic? You can pick up exactly what you need at the nearby Woodstock Farmers Market and head to any of our local trails for a relaxed afternoon surrounded by the breathtaking beauty of Vermont in the Fall. 
  4. We love Vermont covered bridges any time of year. They are charming, historic reminders of days gone by. Surround them in the colorful hues of Fall, though, and they are stunning. There are at least ten covered bridges in and around Woodstock worth seeing – many of which you’ll see as you enjoy scenic drives in Vermont. 
  5. The agricultural bounty of Vermont is worth a taste in the Fall. One of our favorite places to enjoy some fall treats is Sugarbush Farm. While there, don’t miss the chance to see their beautiful chapel in the woods. 

Of course, you can enjoy the best of Vermont in the Fall at one of the best Woodstock, VT hotels. We offer great selections of beer, wine, and cocktails for you to enjoy on our scenic property, along with elevated charcuterie Boards. Let us treat you to a getaway that is as relaxing as it is beautiful. To enjoy fall getaways at elevated Woodstock, VT hotels like ours, you’ll need to plan well in advance. Fall is our busiest season! Book a room today!

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