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How to Do a Fall Weekend in Woodstock, Vermont

For a quick getaway filled with vibrant colors and country charm, you can’t beat a fall weekend in Woodstock, Vermont. With opportunities for hiking, shopping, and fine dining in a classic New England village that looks like a postcard come to life, Woodstock is the quintessential place to take advantage of a seasonal weekend escape.

Where to Stay in Woodstock, Vermont

Head to the Woodstock Inn & Resort, a fully renovated and bigger-on-the-inside historic Colonial inn that’s been transformed into a year-round resort experience—complete with a spa, golf course, and upscale farm-to-table dining scene. Elegant yet cozy, the Woodstock Inn is centrally located on the town green, right in the middle of the action and within easy walking distance of nearly all seasonal activities.

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The highlight of every room at the Woodstock Inn is the natural wood-burning fireplaces (precut wood and matches are waiting upon arrival). Start your own fire and then sit back and enjoy warm, romantic nights during your fall getaway.

Fall Weekend in Woodstock: Your Friday Schedule

Arrive in the afternoon—Woodstock is just two hours driving from Boston or five hours from New York City. After check-in at the Woodstock Inn, enjoy complimentary coffee, tea, and cookies in the inn’s conservatory, or wander just minutes from the hotel for coffee and treat at the downtown Mon Vert Cafe.

For dinner, head to the inn’s upscale farm-to-table Red Rooster restaurant, and then settle in for a relaxing evening by firelight in your room. Rest up—you’ll have a busy day tomorrow.

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Fall Weekend in Woodstock: Your Saturday Schedule

Start the day with a leisurely farm-fresh breakfast at the Woodstock Inn, and then walk to the charming downtown (less than five minutes by foot from the inn) where you’ll find an eclectic array of local shops.

Begin your shopping excursion with a stop at Unicorn, known for its kitschy variety of toys, gifts, souvenirs, and jewelry products you won’t find anywhere else. It’s a wonderful place to pick up a special something to remember your trip or get a head start on your holiday shopping.

Next, wander into F.H. Gillingham and Sons, a classic general store in the truest sense, still owned and operated by the family that established the shop in 1886. It’s still housed in the original building, too. Here, you can pick up fresh Vermont cheese, rich Maple syrup, and other local specialties.

For book lovers, the highlight of your morning shopping will be a visit to The Yankee Bookshop, Vermont’s oldest continuously operated independent bookshop (since 1935). Pick up a new read to enjoy back by the fireplace in your room.

If you’re a foodie, hop in the car and drive a half hour to King Arthur Flour. Here you can purchase your favorite fresh ingredients, take a baking class, or enjoy lunch or coffee at the cafe.

After lunch, hit the highways and byways of Vermont to take in the fall foliage—just about everywhere you go will be scenic. Or, for a more active encounter, get a dose of fresh air on a local hiking trail. Hiking trails for all skill levels can be found at nearby Mt. Tom—it’s easily summited in just a few hours, but yields technicolor views of the surrounding valley—or Marsh-Billings-Rockefeller National Park, which is home to miles of mostly flat walking and carriage trails.

Enjoy a Saturday evening dinner back at the Woodstock Inn’s more relaxed in-house restaurant, Richardson’s Tavern. Don’t leave without sampling the cheese fondue for two.

Fall Weekend in Woodstock: Your Sunday Itinerary

After another breakfast at the Woodstock Inn, your first stop on Sunday should be the Billings Farm & Museum, where you can explore one of the best outdoor museums in the country. (Admission is free for guests of the inn.) In addition to being a museum dedicated to preserving Vermont’s rural heritage, it’s also a fully-operational Jersey dairy farm where you can see draft horses, Jersey cows, and even some roaming sheep. Take a tour of the gorgeously preserved 1890 Farm House, where you can see what life was like on the farm during its Victorian-era heyday.

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Across the street, visit the Marsh-Billings-Rockefeller Mansion to find out what it was like to be the wealthiest resident of the community. Originally built in 1805, this home was renovated and modernized multiple times over the next two centuries. Currently, you’re able to catch a glimpse of what it was like when the Rockefeller family left the home in 1997. Guided tours are available at select times.

Finally, return to the Woodstock Inn for a luxurious spa treatment before you head back to reality. From premium massages to multi-layer body treatments and alternative therapies like Reiki and reflexology, you’re sure to find a treatment that’ll allow you to end your fall weekend in Woodstock on a relaxing note.

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Josh Roberts visited Woodstock, Vermont, as a guest of the Woodstock Inn & Resort. Follow him on Instagram at @jauntist and on Facebook JoshRobertsBooks.

By Josh Roberts

Josh Roberts believes the best trips involve long hikes and muddy boots. His life goals haven't changed much since he was a kid: He still wants to be Indiana Jones when he grows up.

Follow him on Twitter (@joshwhowrites) and Instagram (@joshwhowrites), and visit his website (joshrobertsbooks.com) or Goodreads page to learn more about his forthcoming novel.

Josh joined SmarterTravel in 2001, and is an active member in both the Society of American Travel Writers (SATW) and the Society of Children's Book Writers and Illustrators (SCBWI).

In addition to SmarterTravel, he has written for USA Today, The Boston Globe, Yahoo! Travel, The Huffington Post, Airfarewatchdog, TripAdvisor, Jetsetter, ABC News, Oyster, and Business Insider. His travel photography can be seen in Britain and Ireland's Best Wild Places, published by Penguin UK.

The Handy Item I Always Pack: "A lacrosse ball. It's small, lightweight, and works wonders on loosening up tight muscles."

Ultimate Bucket List Experience: "Being the first to discover an ancient lost city. Failing that, visiting as many of the already-discovered ancient ruins as possible."

Travel Motto: "Not all those who wander are lost." -J.R.R. Tolkien

Aisle, Window, or Middle Seat: "Aisle."

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