Fall Road Trip to Woodstock, Vermont: An Autumn Wonderland

by Jan 3, 2021Blog

Farms, foliage, food, covered bridges, antiques, craft beer. Seriously, this place has everything you’re looking for on your next fall road trip.

Woodstock, Vermont harbors a very special place in my heart. It is like a one-stop shop for all things fall in New England. If you want a taste of every fall activity you can imagine, take a perfect photo for your Instagram, or works of iconic New England architecture, then look no further.

Middle Covered Bridge in the city center of Woodstock get’s decorated seasonally.

I go as far as to describe the area as Disneyland-like. There are so many sights and sounds Woodstock offers that most of us from outside the region have only seen in movies. It overflows with Vermont country charm.

You get the best of both the worlds of the outdoors and small cities, as you are never far from charming cafes, farm-to-table restaurants, hiking trails, kayaking, or historic farms.

Relatively well known and often cited as the most photographed town in New England, I was the only person to have visited amongst my circle of friends. That is, until I brought them. This post shares several photos I have taken with my Nikon dSLR, smartphone, and a disposable camera.

But first… Quechee

Quechee Gorge.

There’s no visit to Woodstock without first passing through the town of Quechee first. Quite literally in factt, since you have to drive through to get to Woodstock from the highway.

Quechee’s most well-known attractions are the massive Quechee Gorge and the Quechee Gorge Village. Both are must-stop along your way.

Just before the Gorge comes the Quechee Gorge Village. It is a great and convenient way to sample many classic Vermont experiences, as it is home to a huge antique store, toy museum, restaurants, souvenirs, jewelry, fine spirits, live alpacas, and perhaps my favorite attraction of the bunch, the Cabot Cheese tasting station at the Quechee General Store.


Sadly for our 2020 visit, the cheese samples were not available to keep visitors safe during the COVID19 pandemic. But rest assured, during normal times, this is a great way to fill up between meals and be amazed by the variety of different cheddars available.

Just across the street from the shops lies the Gorge itself. This rushing waterway is anything but hidden, as there is a bridge over the Gorge with scenic viewing lookouts which can be reached on foot.

Despite that, I missed the Gorge my first couple times I visited the area, but I am sure you wont after reading this!

There is a brief and easy hiking trail to the base of the Gorge that I highly recommend. You can walk within the confines of the Gorge directly on the rocks that form it and get a spectacular view of the bridge above.

A video I recorded at the base of the Gorge I recorded in October 2019, a bit before peak foliage.

Autumn Backroads

Before reaching the center of Woodstock, I recommend that you explore on your own, traversing as many dirt roads as you can, as we did. You will be surprised just how beautiful the views you’ll find on these winding backroads can be!

A right turn over the Taftsville Covered Bridge, then a subsequent left turn brings you to the tiny town of Taftsville through Hillside and High Pastures road.

Passing through, you will find the most incredible homes with even more stunning mountainside vistas behind them. I don’t blame you for taking your time here to soak up all the views. Just be wary of the locals who live there.

Up the road, Cloudland Farm offers farm dining and reasonably priced cuts of farm raised meats to boot.

Further towards Woodstock is the now world-famous Sleepy Hollow Farm, in Pomfret, VT. The darling of everyone’s Instagram posts, this farm nestled in the mountain hills has been offering gorgeous sights since the 1780s.

It is easy to see why so many photographers come here, as a the layout of the farm make composing a stunning shot easy. The fairytale like scene that crowds flock for is located just where the road and farm’s winding driveway meet.

Woodstock, Vermont Town Center

Woodstock’s cozy but bustling town center.

A short drive from these mountain side roads brings you to the center of Woodstock. Really consisting of one main road and a small town common, Central Street, the town screams cute and cozy. There is metered parking throughout Woodstock, but you will find free-to-park streets like Pleasant Street that are not far at all. On either side, you will find enough shops and restaurants to leave you with full shopping bags and full bellies.

One of my favorite shops to visit is Woodstock Sports, who specialize in high-end athletic gear and bikes. Why might I, not the most active person on the planet, be so charmed by this place? Simply, it’s the two incredibly friendly dogs that greet you throughout your time browsing.

More from the city center.

Above Yankee Bookshop is Ellaway’s Attic, which offers a treasure trove of carefully selected antiques. A must visit as the owners are very friendly as well!

Of course, you wouldn’t really be visiting Vermont without a stop at The Vermont Flannel Co. to bring home some local and practical style to your wardrobe. Your visit would be incomplete without picking up some maple syrup or other goodies from F.H. Gillingham & Sons, which is a rather large general store just across the street.

Across from the town green is the Middle Covered Bridge, where you are sure to find your fellow travelers causing traffic issues by posing for pictures in front of the iconic roadway. It is worth taking a stroll through the bridge, as either sides offers lovely views of the Ottaquechee River.

Disposable shot with of friends from within the bridge.

A walk further up brings you to the town Green, which hosts farmers markets on Saturday evenings. Across the way is the Woodstock Inn & Resort, another darling of Instagram feeds far and wide. I have never stayed, but it seems to be the place!

The Great Outdoors

A leaf peeping trip would not be complete without at least some time in the outdoors. Luckily, shockingly close and just down the street is the Billings Farm and Museum and Marsh Billings-Rockefeller National Park.

The Billings Farm and Museum is a fully operational dairy farm that is home to award-winning and exceptionally friendly Jersey cows.

The museum offers a variety of daily events where visitors can learn about life on farms, the history of the site, or just an opportunity to hang out with the animals. Check out their daily schedule to get a better idea of what is happening for your next visit.

Oh and don’t forget to pick up some Billings Farm Cheese – the ultimate souvenir in my opinion.

Exploring the Park Grounds

In the adjacent National Park are several fantastic attractions. The Marsh-Billings Rockefeller family built a spectacular mansion in 1805 that has been preserved and is open for visit (well, during typical non-COVID times) for guided tours and a step back in history.

Disposable shot from the farm.

Nearby on the same grounds is The Belvedere. Representing a unique junction in history, this was both the playground for the Rockefeller family and potential saving grace. The two-story cottage complex consists of a pool, garden, bowling alley, and fallout shelter.

Yes, you read that last part right. A fallout shelter was added when the Rockefellers renovated in the 1950’s during the height of Cold War tensions.

Various other structures and gardens litter the park. You can find more complete information about them on the National Parks website.

Hiking at Marsh-Billings Rockefeller

The hiking trail is adorned by fallen leaves and rays of sunshine come October sunsets.

The park features several popular hiking trails. The most popular is easily The Pouge Pond Loop. This short trail is well marked and consists of gravel roads, which is great for hikers of all levels. The hike is a bit steep for the first half, but gets easier as you go and is completely worth it for the view at the top!

The top of the trail brings you to The Pogue pond – a mountaintop water feature. This makes this hike a must do, especially in the fall. You will be greeted with the spectacular color-changing leaves reflecting in the calm and still pond.

The Pogue at the top of the trail loop with Mount Tom in the background.

Definitely do not forget to take pictures while you’re there!

Look how happy Woodstock makes us!

Now, About Eating

Mon Vert Cafe

If all this adventuring has you in need for a pick-me-up, then be sure to stop at Mon Vert Café. This quaint, uncomplicated, but delicious coffee, breakfast, and lunch spot that excels in execution is quite obviously one of my favorite places. It gives you a great way to get a local taste of Vermont, as they proudly feature locally sourced and organic ingredients.

Seriously, I wish my LinkedIn had half the networking the menu has with all the local farms and suppliers listed.

Sipping brews at Mon Vert Cafe.

As a traveler, I prefer simple and quick breakfasts and lunches from local cafes or delis since they usually don’t take much time, but provide a unique local taste and this café is a perfect match. Pick up a simple cappuccino and smoked salmon club on a perfectly crispy baguette for a taste of local Vermont eats nirvana.

Smoked Salmon Club - Mon Vert Cafe
The Smoked Salmon Club from Mon Vert Cafe – featuring a delightfully crunchy baguette and somehow crunchier bacon.

Worthy Kitchen

For dinner, my pick is Worthy Kitchen. Again, keeping with the theme of uncomplicated dining experiences, Worthy Kitchen is a fast-casual restaurant that offers farm-to-table American classics. Everything comes served with a twist in a rustic, but updated environment.

Worthy is perhaps most well-known for their friend chicken of which I have experienced the delights of in the forms of the Chikwich and chicken and waffles. They are always keeping their menu interesting with experimental and temporary items like The Seoul Brotha, a Korean-inspired pork burger.

Worthy Chikwich with truffle fries and buffalo sauce.
Chicken and waffles with blue cheese, sweet potato, buffalo sauce, maple syrup, and brown onion gravy. The best bites had all of these ingredients, believe it or not.

What goes better with all this pub food than a beer? Not only does Worthy have a fantastic selection but they have the one and only Heady Topper. This 8% ABV double IPA is arguably Vermont’s most iconic brew. It’s so beloved that people line up at The Alchemist brewery to get. This citrusy, smooth, and pleasantly bitter beer will quench the thirst of even the most IPA averse.

Out of all the experiences in this post, this might be the most Vermont. The legendary Heady Topper from Alchemist Brewery.

Of course, there are many other fine restaurants in Woodstock worth checking out. These two are the ones I am most familiar with and always stop at, but I encourage you to try others on your own.

I hope you’ll venture out and visit to see why this is such a special and beloved corner of New England for yourself soon (or as soon as we can, at least)!

Where is your favorite place to visit during fall? Leave a comment and let me know below!

Looking for some great travel gear to make your next experience even better? Check out my travel gift guide.

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