Since spending more time in Manhattan, I’ve fallen in love with the state of Vermont. Perhaps it’s that things are far too complicated these days, and Vermont feels like a safer, simpler, and quieter place and pace when compared to New York, Washington, or anything we read on the news. My boyfriend loves driving; I love resorting; and we both love seeing new places. So, road trips to Vermont and the Hudson Valley have become a recurring weekend affair. I pack up my cute Barrington Gifts weekenders, and he rents an unnecessarily cool car, and off we go for a drive.
Driving through Vermont is like opening up the pages of a picture-perfect storybook. The drive from New York to this idyllic Northeastern state is filled with red barns with dairy cows, schoolyards, and classic Victorian houses with white picket fences. It truly feels as though you’re being transported back to a time when things were far simpler—schools were safe, farming made you a living, and you knew your neighbors.
We first fell in love with Vermont driving through its snow, windy roads on a weekend ski trip to Stratton. The popular family destination an easy, accessible ski town for groups of all types and skiers of all levels—read about my trip, here. So, we (my boyfriend and I) did what we always do when we enjoy a place: book another trip. We planned to stay at the charming and historical Woodstock Inn, located in its namesake town.
Not to be confused with Woodstock, New York, the site of the famous music festival, Woodstock, Vermont, is a small town of around 3,000 inhabitants and is quintessentially Vermont in that it looks like not much has changed in the last 100 years.
I am a sucker for charming inns and resorts—Salamander and L’Auberge Provencale in Virginia being two of my favorites, and I can now add Woodstock to the list. The Woodstock Inn & Resort’s history dates back to 1793, when it was opened as a tavern by an early European settler. Fast forward to the 1960s, when it was purchased by the Rockefeller family, rebuilt, and reopened to the public. The Inn is packed with history—with placards demarcating important facts and narrative about the space. Outside, it is a beautiful presence of a white wooden building with black trim. Inside, the décor is classic Victorian, with dozens of cozy seating areas, and spaces to sit alongside the fire, a sun room for reading, and a game room where you can play checkers, chess, scrabble, or tackle a puzzle.
Our room was on the third-floor of the three-level inn and it was decorated in the classic style but with modern, upgraded amenities and touches. As usual, my favorite parts were the bathtub and the bed, which allowed us to have 10-hours of uninterrupted sleep each night.
In addition to the charming resort, the real reason I go anywhere is to eat. So, let’s talk about the restaurant, the Red Rooster. We enjoyed a delicious brunch both days, which is available both a la carte and as a buffet. On Saturday, we enjoyed the a la carte breakfast, in particular the fresh fruit bowl with homemade banana bread, the citrus juice blend, and the Belgian waffles were all memorable and noteworthy.
The bagel and lox were great—classic white bagel with sliced tomatoes, hard-boiled eggs, cream cheese, and fresh smoked salmon. I was skeptical of the waffles, as Belgian waffles tend to bore me, but these were some of the best I’ve ever had. They were moist and fluffy, topped with whipped cream and fresh berries. Between bites, we both pronounced that these were the best waffles we’ve ever had.
Our server, Amy (hi, Amy!) was an absolute delight. She was very knowledgable about the property and the town of Woodstock—and by the end of the brunch, she’d practically laid out our entire day’s itinerary.
While brunch was rather good, it was nothing compared to dinner, which was a truly divine dining experience. The restaurant transforms into a high-end dining experience come evening. It began with a strong start—a delightful, effective waiter and an incredible bottle of French red from one of my favorite wineries. The bread and butter course was special enough that we could have stopped the meal after that. Three types of locally baked bread, and local Vermont butter. It was an utterly divine bread service.
We shared everything—and were particularly impressed by the lamb bolognese gnocchi, made in house and cooked perfectly al dente. The local, grass-fed cut of steak was delicious, but it’s the Italian food and the local Vermont touches that make Red Rooster such a special place.
The eggplant parmesan finally converted me into an eggplant lover, and by the dessert course we were more in love with the food, the meal, and eachother than we’ve ever been.
We were able to experience a couples massage at the spa, which is absolutely stunning. We enjoyed a couples massage—because we love doing weird stuff together—and felt the extreme stresses of work and life dissipate together.
The bright, airy spa had beds for lounging and reading on the sheepskin blankets alongside the fire. Noteworthy: the spa’s tea was particularly tasty and they serve healthy fruit cocktails (yes, the alcoholic kind.)
What I love about the Woodstock Inn is the activities: there’s the spa, but also an athletic and racquet club, to play tennis or take complimentary yoga, a falconry, to experience birds of prey, and, my favorite part, the Billings-Farm and Museum. The farm is owned by the Inn and therefore free and open to guests—it’s a fully operational dairy farm as well as a museum of the area (farm, parks, regional history) in a 1890s farm house, which you can tour.
The farm offers all sorts of scheduled activities, including meet and greets with baby sheep, churn your own butter, and milking a cow. As it’s spring, we were able to meet baby piglets, sheep, and cows and cooed with delight.
Beyond the Inn’s activities, there’s plenty to do in town. Here are our top suggestions:
Hike through the Marsh-Billings Rockefeller National Park. After visiting the farm, we took a four-hour hike through the adjacent national park. It was the perfect spring weather, and the views of the town and forests from the top of the mountain were stunning. There are multiple trail options for different levels—and the concierge has maps for guests that outline the town’s activities as well as all the park’s trails.
Visit the Woodstock Farmer’s Market. The market is packed with Vermont cheese, maple syrup, and food from local purveyors. Plus, a killer sandwich counter and coffee bar featuring locally roasted beans. We spent far too much money on a whole lot of off-the-cuff food stuff and had a blast. Woodstock Farmer’s Market, 949 Woodstock Road, Woodstock, VT.
Visit the town of Woodstock & the General Store. The quaint main street of Woodstock is absolutely darling, and features a few well-appointed gift shops with cute pillows and all-natural beauty products, as well as a general store packed with local goods like cheese and Maple syrup. Appropriately, there’s also a Vermont flannel store.
Dance with the locals to live tunes at Bentley’s. Right on the main street of town lies Bentley’s, which is an American bar and restaurant with live music on weekends. Go early, as establishments in this sleepy little town close early.
The Woodstock Inn & Resort
14 The Green
Thank you to Woodstock Inn for hosting us for the weekend.