There’s something about leaf peeping in small East Coast towns that just makes sense. The gently blowing wind brings in a crisp air and the scent of earthy leaves, balanced out by the warm kiss of sun on your face. A toasty coffee, tea or cider in hand, combined with the fiery hues of the transitioning trees, and the experience is quintessentially autumnal.
This cozy vibe was exactly what my sisters and I were chasing on our latest trip together, and how we ultimately wound up in Woodstock and Stowe, Vermont. The two destinations are quite popular among fall-seeking adventurers, and with their Pinterest-worthy scenery, friendly atmosphere and quaint downtown spaces, it’s easy to understand the allure. For travelers interested in a slow weekend getaway in the autumn months, here’s what you need to know about visiting Woodstock and Stowe.
Woodstock
Located in Central Vermont with a population of around 3,000 residents, Woodstock is pure New England charm. The homes are classy, showcasing their colonial roots through brick exteriors and decadent white columns around the porch. Swinging signage advertises uppity mom-and-pop storefronts, and there’s a quiet luxury exuding from the preserved architecture of the town’s buildings.
Activities
Within Woodstock’s streets, exploring the downtown area and dining on delicate eats encompass most of what visitors can do here. My sisters and I enjoyed snapping photos of the adorably decorated homes on Pleasant Street before wandering into F.H. Gillingham & Sons general store to peruse their trinkets. We also took some time to check out the historic Middle Covered Bridge. There are three in the area, each one notable for its unique display of New England history. Because of the Middle Bridge’s proximity to town, it’s a well-loved stop for photos, though we managed to snag a few without any traffic or people thanks to the early hour we visited.
Outside of Woodstock, my traveling trio took advantage of the beautiful Vermont landscape with stops at natural landmarks, like the Quechee Gorge. Nicknamed “Vermont’s Little Grand Canyon,” the state’s deepest gorge is only a 15-minute drive from town. The numerous hiking trails were a great way to explore the area, and entrance was free, making this stop ideal for budget travelers.
Our final activity in Woodstock was heading out to the 550-acre Sugarbush Farm. The hillside property has been in the Luce family for generations, specializing in cheese and maple syrup production (both of which visitors can try). To say my experience sampling these products was “transformative” would be a grave understatement; my taste buds were happy dancing all day long! The syrup exploded with sweetness and flavor before gently dissolving on the tongue, while the rich creaminess of the cheese rivaled even some of Wisconsin’s best. Travelers can purchase the products they sampled inside the gift shop or embark on a journey into the maple trees to learn how syrup is collected and produced.
Lodging
Of course, what’s a small-town visit without a stay at a cozy inn? In the immediate area, the Woodstock Inn & Resort, The Shire Woodstock and On The River Inn are great options for travelers interested in these types of accommodations. Their prime location and overall atmosphere do put them in a higher price range than a standard hotel, though budget-friendly visitors can find other alternatives in the neighboring towns of Killington or Bridgewater.
Dining
Woodstock may not have a huge variety of food offerings, but what they do have is done well. Fine dining at establishments like Oakes & Evelyn, Santé and Au Comptoir is available, though my travel group preferred to stick to less expensive options. Check out where we ate:
- Positive Pie: A standard pizza spot with appetizers, salads, sandwiches and cheesy goodness, Positive Pie is versatile. Quick by-the-slice pizzas make the restaurant a fast, on-the-go lunch spot, while sitting down at a table is ideal for dinner.
- Mont Vert: There’s a reason this cute café is always bustling, and that’s because the food is incredible. Serving breakfast and lunch, Mont Vert has everything from seasonal coffees, breakfast goodies and salads to deli sandwiches and wraps. While I do recommend dining here at some point, know that service can move slowly because of its heavy foot traffic.
- Woodstock Scoops: A Vermont delicacy, sweet-treat lovers must try a maple creemee. The dessert is comparable to soft serve ice cream, but its light and airy consistency is otherworldly. Tip: Try your maple creemee with a pumpkin twist for the most delightful combination of fall flavors.
- Woodstock Farmers’ Market: An alternative to sit-down restaurants, the Farmers’ Market has a great variety of foods, including grab-and-go breakfast or lunch sandwiches, coffee, bakery treats, groceries and produce. Shopping here for easy and nutritious meals was another way we cut back on food spending.
Other Insights
True to small-town fashion, travelers don’t need more than a day to explore Woodstock. The streets fall quiet after nightfall (even on the weekends), with all the action occurring during the day. Visitors can beat the crowds by getting into town before 9 a.m., securing good parking spots and a table at the local cafes.
Stowe
In a similar fashion to Woodstock, travelers won’t need to allot much time in their itineraries to explore Stowe. My sisters and I ended up condensing our visit into one afternoon when we realized we were quickly running out of steam, but a full day in town would likely be ideal for most visitors.
Activities
We started our exploration of Stowe with a visit to the Community Church. The landmark, built in the classic New England colonial style, is synonymous with the town, as its origins trace back to 1863. We found the best view of the structure to be closer to the public parking lot near the town entrance because from that vantage point, the church is set aglow by the distant tree-lined horizon.
In the heart of town and along the main thoroughfare, storefronts and boutiques are in abundance for those who love to shop. From Once Upon a Time Toys and Bear Pond Books to In Company Clothing and Stowe Mercantile, nearly every kind of goodie or keepsake visitors can think of is housed within.
For more hands-on activity options, travelers can head to a number of attractions in Stowe. The Cold Hollow Cider Mill is one, and it’s conveniently located up the road from the downtown area. The mill has become rather well-known among tourists because it operates with its original 1920s press, preserving traditional cider-making methods. Local products like fresh apple cider donuts, honey, pumpkin rolls and pie are also available to purchase, so make sure to visit with an empty stomach.
Speaking of sweet treats, the Ben and Jerry’s Factory is only a hop, skip and a jump away from the mill. It costs $6 for adults to take a 30-minute tour of the grounds, but seeing as the Waterbury location is the only B&J factory open to the public, it’s a worthy price to pay. Guests will have the opportunity to learn about the company’s history, see production in real time and, of course, get their hands on a few samples. Don’t forget to head outside to explore the Flavor Graveyard, where tombstones mark past concoctions and their production years.
Dining
As our visit to Stowe was quick, my sisters and I only ate in town once, at The Bench. Like many other restaurants nearby, this establishment served standard pub fare and comfort meals. Travelers will find similar menus at a majority of the dining spots in Stowe, ranging in price rather than food offerings.

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