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NYC Escape: Outdoor Adventure Meets History In Woodstock, Vermont


The Woodstock Inn & Resort makes an amazing weekend getaway from NYC

Disclosure: This post is part of a local trips series and giveaway I’m doing in partnership with Amazon. Amazon compensated me and provided my travel and accommodations in exchange for writing about my travels. Regardless, everything I have said in the post reflects my honest observations and opinions from my solo road trip.

“Welcome to the Woodstock Inn & Resort. You’re just in time for afternoon tea and cookies in the Conservatory.”

To celebrate the launch of Amazon’s new Amazon Destinations — a booking site helping travelers discover nearby getaways and hand-curated accommodations within driving distance of Los Angeles, New York City and Seattle — I’ve rented a car and driven five hours to the historic village of Woodstock, Vermont, established in 1761 by settlers from Massachusetts. The resort perfectly fits with the local aesthetics, charming 18th and 19th century homes with lots of Victorian, Federal and Greek – Revival details, leafy green parks and gardens, and sidewalks lined with local boutiques.

To be honest, when I first heard the word “resort” my mind immediately pictured crowded buffets and screaming children splashing the pool. However, while the Woodstock Inn & Resort does indeed have a pool (two, and a hot tub!), it retains a refined yet relaxed feel.


The Woodstock Inn & Resort library and game room


Maple cream and chocolate, anyone? A delicious dessert at the resort’s Red Rooster restaurant

Surrounded by the Green Mountains, the property features impeccably manicured grounds, a private garden with lounge chairs, a stately library with puzzles and books, an LEED-certified spa, a game room, onsite restaurants and bars, a country club, tennis courts and free bike rentals. There’s also a huge fitness center with a heated indoor lap pool, steam room, whirlpool, gym, weight room, and fitness classes ranging from Hatha Yoga to Aqua Aerobics and beyond. My guestroom is also impressive, showcasing locally-crafted wooden furniture, a Vermont marble bathroom with a nice tub and natural Vermont forest-scented bath products, and views of the surrounding mountains.

A Passion For Preservation

Nature and historic preservation are major highlights of both the hotel and the Woodstock itself, which makes sense as they were also passions of Laurance Rockefeller, both a businessman and a conservationist. Woodstock was the home of the woman he married, Mary French, and it quickly became a major focus of his conservation work. Today, the local Marsh-Billings-Rockefeller National Historical Park — a 10-minute walk from my hotel — is Vermont’s first national park, absolutely a must-visit.

Which I do; however, instead of going straight to the National Historical Park entrance I cross the street from the Woodstock Inn & Resort and walk over a whimsical wooden covered bridge. Following the map given to me at reception, it takes no more than 10 minutes before I’m standing at the base of Mount Tom in Faulkner Park.

Yea, I’m the type who likes to work for my attractions.


Hiking through Faulkner Park

While there are a few options from here, I opt for Faulkner Trail, which allows me to summit Mount Tom and enjoy aerial Woodstock views before continuing up to the South Peak or following Mount Tom Road right into Rockefeller National Historical Park. I choose the later, trying to make the most of my packed day.

As I hike, the scenery is mainly bird-filled woodland, although I also spot a hot orange salamander, and is extremely peaceful. In fact, aside for two 70-year old men doing a birthday summit, I’m completely alone, immersed in the smells, sights and sounds — mainly the hooting of the Barred owl and the rush of stream water — of Vermont forest.

Side note: While Woodstock is an extremely safe destination, I don’t recommend hiking alone without bringing a safety whistle and pepper spray, here or anywhere. Better safe than sorry!

While the steepness varies, for the most part it’s a gradual climb, although there are a few big (but manageable) rocks to climb up. Every uphill step is worth it though, for the views that welcome me at the top, making Vermont appear like an endless garden of green.


There’s a little but of climbing on the hike, but nothing unmanageable


Views from atop Mount Tom

As I approach the National Historic Park my options for trails become limitless. It seems every 10 minutes there are markers for new outdoor explorations, from lake loops to open grassy fields to foliage-filled trees. I also encounter a few more people, likely because this park is more popular than the latter, which may affect which you choose if you decide to make a similar journey.

Mesmerizing Pogue Lake

I opt for a flat and scenic trek around the 14-acre (6-hectare) Pogue Lake, which entrances me with its mountain reflections and beautiful Great Blue herons hungry for bass fish. To hike completely around the lake takes me about 30 minutes including stopping to take photos, an excellent option for someone who wants an uplifting taste of Woodstock. It’s interesting to note petrified wood poised around the Pogue, with notes like “the lough waters can petrify wood” (ha!).


I didn’t make this, just stumbled upon it in the forest. A fun and inspirational find!


Which way to choose? I went with The Pogue


Pogue reflections

At this point I’m seeing signs that also point to the Visitor’s Center, which I didn’t originally see as I came in an offbeat way. From the lake it’s about a 1.5-mile (2.4-kilometer) flat hike to the National Historical Park entrance, wrapping you in the shade of the centuries-old sugar maples and hemlocks the entire way. The wider trail — actually used for carriages in the late 1800s — seems to welcome more families and trail runners, although it could also be the amenities like a forest center and visitors center.

Exploring Vermont Farm Heritage

Suddenly, I’m back on the road, right across the street from Billings Farm & Museum. Awesomely, the $14 admission to the attraction is included for Woodstock Inn & Resort guests, although anyone can tour the museum portion with its 30-minute film and two-floors of educational exhibits, artifacts, old photographs and scene recreations showing the old and simple yet effective farming methods and the 19th century farm life.


A display on milk through history


Wandering the Billings Farm Museum

As Billings is still a working farm, it’s worth it to pay admission to tour the animal and wagon barns, grab a homemade ice cream in the dairy barn, stroll the heirloom garden and orchard, photograph the sheep and heifer pastures and take a tour of their well-preserved 1890’s farmhouse. Each day also brings educational activities, like “Meet Our Baby Chicks,” “Up Close With A Jersey Cow” and an interactive “Introduction To Milking.”

Billings Farm is run in partnership with the National Park, both of which have rich history. After the American Revolution Vermont became overrun with settlers, who also cut down local forests to a scary extent. It was George Perkins Marsh who first took local concern to action. A farmer, congressman and world traveler, Marsh had seen both the good and bad of human impact on the environment, even penning the book “Man and Nature” in 1864, one of the first texts ever published on environmental responsibility.


Exploring Billings Farm & Museum


Sheep on Billings Farm


A peek inside the chicken barn

In 1869 an attorney named Frederick Billings took over Marsh’s farm, also sharing his concern for the local environment, especially as he had returned from his home state of Vermont from California after the Gold Rush to find it almost barren. He turned the farm into a model of sustainable development, implementing a forest management program and importing purebred Jersey cows, creating a high quality local dairy farm.

After Billings passed away his wife, daughters and even granddaughter, Mary French, continued his work. In 1934 French married Laurence Rockefeller, and the two furthered the local passion for natural development by funding what is today Vermont’s first national park. This is only one of 20+ national parks the couple created or enhanced, so you can see their love of their country’s land was very real.

My favorite Billings Farm & Museum experience is touring the 1890 Farmhouse, starting with seeing the historic equipment used to turn cow’s milk into butter. Despite that in the late 19th century butter ranged from $0.35-$0.50, it was actually expensive for the times, and most locals opted to make their own instead. As we move up the stairs of the house we come to the period rooms, pantry and kitchen, with some original furnishings like the standing office desk and safe. A walk-in closet full of period clothing, commode-equipped bedrooms, historic cooking tools and  cozy family room with old photographs and fainting chair makes the Billings’ story really come to life.


A historic farmhouse tour


Beauty on the farm

A Whimsical Family Farm Experience

Before visiting Woodstock I knew I wanted a farm experience, and I was debating between Billings and Sugarbush. In the end I do both, and am glad I did as each provided a very different Vermont farm experience. While Billings is enormous and has that air of historic preservation, Sugarbush Farm is a small family-run establishment offering free structured tastings of 14+ cheeses and four very different maple syrups made onsite — and that’s not counting the myriad complimentary samples of jams, spreads, honeys and booze-infused jellies laid out around their farm shop.


Seeing first-hand how sap is procured from the trees


Lots of delicious local tastings — for free!


The Sugar House has beautiful views and sweet local maple syrup

It’s a truly immersive experience, even offering a 15-minute Maple Walk through the maple trees to see how sap is taken from the trees, and a sugar house bringing to life the boiling process that transforms maple sap into maple syrup. Best of all, the venue has been run by the same family since 1945, and is now in the third generation, proudly working the 550 acres of land and 6,000 maple trees.

Delicious and insightful, especially for culture carnivores traveling on a budget.

Getting Lost In Historic Woodstock

I never visit a place without spending at least a few hours wandering and getting totally lost, and Woodstock is certainly a place to enjoy the ambiance, especially as almost every building seems to be listed on the National Registry of Historic Places.


Wandering historic Woodstock


Eating a Whoopie Pie on the Ottauquechee River

Staying mainly on Elm and Central streets, I peruse the titles of Yankee Bookshop before making my own organic peanut butter at Gillingham’s General Store, and savoring a snack of homemade deviled eggs and whoopie pie at The Village Butcher, who also have an impressive selection of local wines, cheeses, maple syrups and meats.

After photographing the 19th-century First Congregational Church with its Tower Clock and Paul Revere Bell, I do a self-guided gallery tour, visiting cozy and creative venues like The Collective—The Art of Craft, The Woodstock Gallery, Gallery on the Green and the eclectic gift-filled Unicorn.


An impressive array of local maple syrups at The Village Butcher


The First Congregational Church in Woodstock

A Vermont coffee laced with organic milk at Mon Vert Café gives me a needed energy boost, and continue wandering over a beautiful bridge to photograph the Ottauquechee River. At night, Bentleys Restaurant provides a delicious menu of a burger and fries paired with live local music.

What’s your favorite Woodstock experience or NYC weekend getaway? Please share in the comments below.

Essential Information:

Getting There: To reach Woodstock, Vermont, I rented a car. Avis is one recommended company. For almost the entire ride I was on I-95 North. Click here for specific directions from your starting point. The drive is 4-5 hours depending on traffic.

Getting Around: While it’s recommended to have a car to reach some of the further out farms and attractions, there is plenty to do — including most of Woodstock’s main attractions — within walking distance of the Woodstock Inn & Resort.

Civil War History: A major reason people visit Woodstock that I did not explore in depth is its Civil War history. If this interests you, check out this self guided tour map of some important local Civil War sites. You can also call the National Park System at 802-457-3368 ext 22 to schedule a tour with a guide.

Woodstock Inn & Resort: Rates start at $203 per night, which includes a large number of amenities like admission to the Billings Farm and Museum, parking, very high speed Wi-Fi, in-room coffee and tea, spa facilities, morning and afternoon tea, fitness classes and more. Contact: [email protected]; (888) 338-2745.

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About Jessie Festa

Jessie Festa is an New York-based travel content creator who is passionate about empowering her audience to experience new places and live a life of adventure. She is the founder of the solo female travel blog, Jessie on a Journey, and is editor-in-chief of Epicure & Culture, an online conscious tourism magazine. Along with writing, Jessie is a professional photographer and is the owner of NYC Photo Journeys, which offers New York photo tours, photo shoots, and wedding photography. Her work has appeared in publications like USA Today, CNN, Business Insider, Thrillist, and WestJet Magazine.

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