As everyone knows, Vermont is chock full of pretty little villages (hello, Grafton!), each more exquisite than the next, and picking a favorite is near impossible. I must admit though that upon arriving in Woodstock, I felt very much as if I had found the one, the fairest of them all.
First settled in 1765, Woodstock grew in popularity as a publishing center in a very attractive location, luring wealthy families away from the big city. What sets this village apart is its sheer elegance which is on display everywhere from the quaint downtown area to the graceful mansions dotted along its charming streets.
The compact downtown consists of only two main streets, zero traffic lights, and a plethora of boutiques, galleries and restaurants attesting to the village’s upscale residents and visitors.
A 130-year-old general store has 8,000-square-feet of locally-made gifts and all the necessities you didn’t know you needed, from maple cookies and folk puzzles to camping equipment.
Cozy cafes with street-facing terraces offer both light nourishment and front-row seats to stop and marvel at the magical display that unfolds every season. For a quick and healthy lunch, stop at Soulfully Good Cafe which sits on a quieter stretch of the main street.
The crowd around Mon Vert Cafe is testament to the excellent coffee and organic brunch fare at the perpetually busy eatery. If pressed for time (or just dying for that A.M. jolt of caffeine), take your order to go and sit at one of the picnic tables across the street or wander to the nearest park 2 mins away.
Well hidden and even more scenic, Abracadabra Coffee Co was by far my favorite morning discovery. Down a little path leading to the river just off the main road you’ll find the beloved local coffee roaster’s red building and the best espresso and cold brew drinks around. Even better – the shop is right next to a park with plenty of outdoor tables right by the river with views of fields and mountains.
Or take your coffee for a walk and sit at one of the benches set by the little brook that crosses Central Street. It is flanked by historical buildings as it winds its way through the village – simply beautiful.
Woodstock’s ideal size is part of its appeal (population is around 3,000) and one can easily wander around the quiet residential streets to take in the beauty from a slower-paced era.
The lovely village green is smack in the middle of it all, literally a stone’s throw from the town’s main intersection and many would say the heart of the village.
Standing anywhere in “The Green” gives you camera worthy moments as pretty much every building and home on its periphery is on the National Register of Historic Places.
A 360° tour on your heels will give you a comprehensive review of the different architectural styles from the 19th and 20th century – so many handsome homes all in one place!
Crowning the green with its outstanding entrance and manicured gardens, the Woodstock Inn & Resort epitomizes the ‘impeccable historic’ feel of the village.
The luxury hotel is one of many contributions from the Rockefeller family in Woodstock and one of the finest places to stay in the state. From lounging on the gorgeous lawn and relaxing at the spa to feasting at one of the in-house fine dining restaurants, a stay here will definitely give you a taste of timeless elegance.
Of course, this being Vermont there’s an impossibly pretty covered bridge just off the green that will lead you to another picturesque part of the village.
The gently flowing Ottaquechee River forms a dreamy backdrop to some more handsome homes.
Within five minutes of walking, you’ll find yourself in front of another one of Woodstock’s delights: Mount Tom. Smack into the village, this small mountain is the perfect lazy hike to work off some of that Vermont beer and cheese while immersing yourself in nature. The trail entrance is right on Mountain Avenue just behind the covered bridge.
It’s a gentle ascent to the 1,200-foot summit and 30 minutes will get you there without breaking too much of a sweat.
You would have gladly climbed a lot more for that kind of view though…this is the biggest bang for your bucks around here.
You can take in the entire village from up here, spotting the covered bridge, the green, and all of Woodstock’s glory in one big, splendid panorama.
You’ll also get up close to the star of Mt Tom that shines down over the village during the Christmas period since the end of WWII, and the cross that gets illuminated for Easter.
Back down, you can continue to stretch your legs by visiting the Billings Farm and Museum, a working dairy farm and agricultural museum set in a restored 1890 farmhouse.
Hop in your car and drive the short distance to Farmhouse Pottery, a dreamy artisanal houseware shop housed in a former bible bindery.
The old-world pottery studio is in plain view from the shop where you can see artisans shaping the clay into gorgeous, minimalist kitchenware right before your eyes.
The elegant simplicity and top notch quality of everything on offer here will surely find a place in your home or as a cherished gift.
You won’t want to leave Woodstock at this point, but when you must, the pastoral surrounding countryside will take a bit of the sting out. Follow the river East to Taftsville for a colorful photo op with the famous bright red covered bridge.
Completed in 1836, it is one of the oldest covered bridges in the nation, and one of the longest, spanning 189 feet.
And any dirt roads in the vicinity is likely to give you that bucolic red barn scene that is so typical of the region and never fails to charm. Whether you brave the hordes at peak foliage time, partake in the numerous winter activities before cozying up in the village, or enjoy summer’s long days of hiking/boating/meandering, Woodstock and its exquisite natural surroundings will give you that quintessential New England getaway in the prettiest of packages…
