It’s Time to Start Planning for Fall in Vermont

Jackson House Inn, Woodstock Vermont

Vermont stands out as an idyllic destination for a fall getaway, offering an unparalleled display of autumn’s splendor. The state’s scenic landscape, characterized by its rolling hills and verdant valleys, transforms into a vibrant mosaic of reds, oranges, and yellows each fall. This seasonal metamorphosis attracts nature enthusiasts and photographers alike, eager to capture the ephemeral beauty. The crisp, cool air and the rustling of leaves underfoot enhance the experience, making every stroll through the countryside a sensory delight.

Among Vermont’s many charming locales, the village of Woodstock holds a special allure. This picturesque enclave embodies New England charm with its historic architecture, quaint shops, and friendly ambiance. As you wander through Woodstock’s streets, you’ll find yourself surrounded by the quintessential autumn landscape, complemented by the village’s timeless elegance. The community’s welcoming atmosphere invites leisurely exploration, and the surrounding countryside offers endless opportunities for outdoor activities, whether it’s hiking, apple picking, or simply savoring the stunning vistas.

For those seeking an unforgettable fall retreat, staying at one of Woodstock’s premier hotels is essential. These accommodations provide a perfect blend of comfort and luxury, ensuring that your stay is as memorable as the scenery. With exceptional service and amenities, these hotels offer a sanctuary where you can unwind after a day of exploration. Experience the best of Vermont’s autumnal charm by choosing a distinguished Woodstock hotel for your fall getaway, where every detail is designed to enhance your enjoyment of this enchanting season.

Woodstock VT Hotel & Bed and Breakfast Lodging Options from Jackson House Inn
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Front of the Jackson House Inn, one of the best Woodstock Vermont hotels for fall getaways

Unwind at One of the Best Woodstock, Vermont Hotels

As a new year approaches, there’s no better moment to whisk your beloved away for a Vermont couples getaway. Whether you visit during winter when this enchanting village is blanketed in a shimmering layer of snow or later when the fall foliage is at its peak, you’ll soon discover what we already cherish: Woodstock, Vermont, is the quintessential destination for a romantic escape in New England. This experience becomes even more extraordinary when you stay at one of the most refined Woodstock Vermont hotels.

Couples retreat to our hotel to celebrate anniversaries, birthdays, babymoons, honeymoons, and any other special occasion—or simply to unwind. Our property boasts numerous features that make it an exceptional Vermont couples getaway, beginning with our enduring tradition of excellence. The Jackson House Inn has cultivated a reputation for a classically elegant yet casually sophisticated atmosphere over its decades in operation, a tradition we proudly uphold for all our guests.

Located just outside downtown Woodstock, our hotel is situated on a picturesque parcel of land in the serene countryside. Here, the focus is on escaping the hustle and bustle and savoring the serene moments that only a sophisticated property like ours can offer. As you arrive for your Vermont couples getaway, you’ll be instantly transported to another time and place. Stepping into the Jackson House Inn, you’ll be warmly welcomed and treated to impeccable hospitality, surrounded by museum-quality art and timeless antique furnishings. The ambiance creates the perfect backdrop for your romantic weekend away.

Unlike larger Woodstock Vermont hotels, we offer a select number of guest rooms, ensuring an inviting and peaceful environment. Each room is uniquely decorated with a blend of classic and contemporary styles, equipped with all the modern amenities you desire for your Vermont couples getaway. Expect to find local bath products from Whisper Hill Bath & Body, luxurious Frette linens with Anichini coverlets and decorative pillows, plush robes, and more.

Beyond your guest room, our Inn features numerous common areas, including our charming tavern, where we’ll gladly craft a cocktail or pour you a glass of wine or beer from our fantastic selection. Outside, you’ll discover three acres of paradise to enjoy during your Vermont couples getaway. Our grounds include beautifully landscaped gardens with a firepit and several private seating areas, a trout pond with seating and a dock, a gentle stream, and more. It’s the perfect setting for a leisurely stroll or relaxing in style with a delicious drink in hand—amenities unmatched by other Woodstock Vermont hotels.

In the morning, delight in a signature experience at the Jackson House Inn: a sensational multi-course breakfast. Serving you breakfast is a simple act that makes a profound impact, not only because it’s delicious but also because it’s a true pleasure to have someone care for you in this intimate way. We relish the opportunity to craft breakfast for our guests, taking pride in the array of local, freshly made dishes presented to you each morning. We handle all the details while you sit back and enjoy the perfect Vermont couples getaway!

Woodstock VT Hotel & Bed and Breakfast Lodging Options from Jackson House Inn
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Covered Bridge in Woodstock in the Fall - one of the best things to do while staying at our Woodstock, Vermont hotel

The Best Things to Do in Woodstock This Fall

Experiencing Woodstock, Vermont in the fall is an immersion into a realm of exquisite autumnal beauty and rich cultural offerings. The village presents a delightful array of activities that cater to diverse interests. Stroll through the historic streets lined with vibrant foliage, where charming boutiques and artisanal shops beckon with unique treasures. The local farmers market is a feast for the senses, offering fresh produce and handcrafted goods. Outdoor enthusiasts can explore scenic trails that offer breathtaking vistas of the surrounding countryside, while history buffs will appreciate the well-preserved landmarks and museums. Culinary delights abound, with farm-to-table dining experiences that showcase the region’s bountiful harvests. Each activity in Woodstock provides a distinct opportunity to savor the essence of Vermont in the most picturesque season.

Make Woodstock your home base this fall and immerse yourself in the scenic charm that greets you at every turn. To fully enjoy your trip to Vermont in the fall, planning ahead is essential. By securing your reservations early, you can ensure you have the flexibility to create the itinerary of your dreams. Beyond the picturesque drives, we’ve curated a list of even more wonderful ways to experience Vermont in the fall. From hiking to apple picking, each activity offers a unique perspective on the season’s beauty.

  1. Few experiences rival the magic of scenic drives in Vermont during the fall, especially when the sun’s warm rays illuminate the already breathtaking landscapes.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: 
  2. Hiking is perhaps the best way to witness Vermont’s fall foliage up close. Trails like the 4.2-mile Pogue/Mt. Tom loop or the scenic paths around Mount Peg offer stunning bird’s-eye views of charming towns and vibrant landscapes.
  3. For an exhilarating adventure, head to Saskadena Six, where hiking and mountain biking trails provide impressive vistas of the fall scenery.
  4. A drive to Quechee Gorge, coupled with a treetop walk at the Vermont Institute of Natural Science, adds a touch of wonder to your itinerary.
  5. For a charming fall picnic, gather provisions at the Woodstock Farmers Market and find a serene spot along one of the local trails.
  6. The historic covered bridges, draped in autumn hues, offer a picturesque glimpse into Vermont’s past.
  7. Don’t miss a visit to Sugarbush Farm, where you can savor local delicacies and admire the beautiful chapel in the woods.
  8. Cloudland Farm


To complete your perfect fall getaway, stay at one of the finest Woodstock, VT hotels. These accommodations offer not only luxurious comfort but also the best of Vermont’s seasonal delights. Enjoy a selection of local beers, wines, and cocktails on the scenic property, along with exquisite charcuterie boards. Let us provide a retreat that is as relaxing as it is beautiful. Given that fall is our busiest season, planning well in advance is crucial. Book a room today and indulge in an unforgettable autumn escape in Woodstock, Vermont.

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