Vermont: Small in Size, Big on Charm

Discover why the New England state should be on your must-visit list

When my parents inherited a tiny house in Vermont in the 1990s, it introduced us to a part of the country that was probably as unlike our Southern California home as it could be, from its place on the U.S. map, climate, and vegetation to its general pace of life. It was also the beginning of a lasting love for this corner of the country.

Though diminutive — Vermont is just one-fifth the size of England — it’s a veritable treasure trove of adventure, history, rich natural beauty, and a distinctive New England allure that quickly captures the heart of anyone who visits. That allure abounds from towns like Shelburne in the north to Bennington in the south, and in central Vermont, Woodstock is a shining example of everything there is to love about the state.

With fewer nearby urban hubs than some of its larger neighboring states, reaching Woodstock might require a little more effort, but it’s rewarded in spades upon arrival. You’ll most likely enter the town via Route 4 (where, by the way, the speed limit is not merely a suggestion, so take heed when it says the limit is 25 miles per hour or the first Vermonter you meet may be a state trooper), and even before you reach the center of town, must-stop establishments invite you to pull in and embrace Woodstock’s relaxed cadence from its outer boundaries before moving into its heart.

Worthy Kitchen draws locals and in-the-know visitors for hearty farm-to-table fare complemented by a generous list of local brews on draft as well as a cocktail list. This order-at-the-counter casual spot on Route 4 is always packed, so if you know when you’ll be driving in, it’s best to make a reservation. The comfort food-laden menu is tempting from top to bottom, with juicy burgers and a knockout chicken sandwich with pickles and ranch dressing as its stars, plus daily specials and fresh salads. It’s the perfect intro to the delicious — both figurative and literal — authenticity that exemplifies Woodstock’s character.  

As you continue into town from Worthy Kitchen, a sharp right turn in Route 4 signals the next stop: The Farmer and the Bell. Husband-and-wife owners Ben (the farmer) and April (the head baker), present both sweet and savory dishes and treats on the delectable menu, which is crafted with ingredients curated from local farms and farmers. What began as a pop-up quickly became an institution, and April’s coveted crullers have achieved mythical status, often selling out well before this Thursday-through-Sunday establishment locks its doors at closing time.  

Downtown Woodstock unfolds along Central Street like a storybook village, anchored by The Green, a sweet park space that is often host to community markets, events, and gatherings. Overlooking the park on one side is the stately Woodstock Inn & Resort, a historic hotel that’s deeply connected to the village in which it sits and a perfect place to call home for your stay in Vermont.

Here, guests (and their dogs) luxuriate in rich, timeless interiors that embody classic New England style. Multiple dining venues span casual eats at Perley’s Pourhouse and Fairway Grill to the contemporary Richardson’s Tavern and upscale, award-winning Red Rooster. For an even more exciting experience, book a Red Barn Dinner at Kelly Way Gardens, a farm-to-table program that supplies fresh produce to the Inn’s dining venues. These intimate, chef-led dinners take place in the actual barn, and feature wine pairings and community tables — a wonderful way to connect with fellow guests as well as local Vermonters over a delicious meal.  

A host of activities that range with the seasons await at the Inn and with its partners, including golf at the Woodstock Country Club, falconry, fly fishing excursions, skiing, and tennis and pickleball, while The Spa at the Woodstock Inn invites pure indulgence and relaxation. A short drive from the Inn is Billings Farm & Museum, a lovingly operated working dairy farm where you can nuzzle sheep and goats, meet newborn calves, and learn about the farm’s history. A regular calendar of events offers ample opportunity for a more immersive visit, from live music and local beers at Moos & Brews to guided stargazing nights and seasonal festivities. It’s a wholesome, family-friendly, must-visit destination that shouldn’t be limited to first-time visits to Woodstock; its genuine, timeless charm will draw you back every time you return. Entry to Billings Farm & Museum is complimentary for Woodstock Inn & Resort guests. 

Just across the street from Billings Farm is the Marsh-Billings-Rockefeller Mansion, the former home of Laurance S. and Mary F. Rockefeller, whose deep commitment to conservation of the environment has shaped not only Woodstock but the country. Take a guided tour of the mansion for insights on how this influential pair lived and established a legacy of environmentalism that echoes throughout the town’s culture and community through use of locally sourced goods and resources and mindful practices. 

It’s a short stroll back into town from the farm and the mansion (which together comprise Marsh-Billings-Rockefeller National Historic Park), and Central Street, Woodstock’s main street, is lined with delightful boutiques selling clothing, toys, jewelry, art, and even a classic general store. Cool off in the summer with an ice cream from Woodstock Scoops in the afternoon, or seek a slightly punchier refreshment at Au Comptoir, the buzzy new destination just across the street, created by the co-founder of the lauded Farmhouse Pottery (which you can also visit a little farther down the road).

Speaking of handcrafted goods, while technically not in Woodstock but neighboring Quechee (pronounced Kwee-chee), the world-renowned glassmaker Simon Pearce is a local landmark. Come to watch the skilled artisans create this stunning glassware that’s now found in American embassies worldwide, and stay for lunch in the flagship store’s restaurant that overlooks the Ottauquechee River. Whiskey lovers can stop in for a taste of Vermont’s own WhistlePig Whiskey at the WhistlePig Whiskey Parlour just steps from Simon Pearce, and to its other side is one of Vermont’s famous covered bridges — three icons tucked side by side. 

If you’re up to explore even more of Vermont’s famous names, a short 30-minute drive from the Inn to Norwich, Vermont, can deliver you to King Arthur Baking Company’s Café, Bakery & Store. Snap a regal photo sitting in the flagship’s King Arthur throne before grabbing sandwiches to enjoy at the picnic tables outdoors if the season allows before browsing the store, where bakers of all levels will truly feel like a kid in a candy store. For a taste of family adventure, head to the Vermont Institute of Natural Science, or VINS. Here, you can hike, play, explore animal exhibits, and experience life in the trees with the Forest Canopy Walk.

History buffs can stray to nearby Plymouth Notch, Vermont, to visit the Calvin Coolidge State Historic Site, where the 30^th president was born and raised. It’s a fascinating step back in time as you walk through his home and other buildings including a general store, one-room schoolhouse, and a cheese factory.   

No visit to this corner of Vermont is complete without taking a moment to appreciate the Ottauqhechee. This stunning crystal clear waterway weaves through Woodstock and Quechee, sometimes tranquil, sometimes thundering, depending on your vantage point and the season. In summertime, grab a tray of popcorn shrimp or an ice cream cone at The White Cottage before dipping a toe (or more) in to cool off in summer, or head to the Quechee Gorge to observe its rugged beauty from 165 feet above.  

From its natural beauty that will take your breath away to its singular, timeless charm, Vermont is the perfect New England escape you’ll want to visit again and again.