Woodstock has a new farm-to-table dining destination, and after one of the best meals I’ve had in Vermont in some time, this is one you’ll want to know about.
Oakes & Evelyn Local favorite: Oakes & Evelyn – Woodstock, the beloved Montpelier restaurant known for its creative, seasonally driven food, opened its second location at The Jackson Local favorite: The Jackson in Woodstock in June 2025. Chef and owner Justin Dain opened the original Oakes & Evelyn in Montpelier in 2021, building a menu around New England ingredients, relationships with local farms and dishes that feel distinctly Vermont without being predictable. The Woodstock restaurant brings that same approach to a completely different setting, taking over the light-filled dining room inside The Jackson, a boutique inn just outside Woodstock Village.
And I personally love when one of the best meals of a trip is waiting downstairs from your room.
The combination of The Jackson and Oakes & Evelyn makes this an especially good option for a romantic Woodstock getaway. Check in, settle into your room, have a cocktail before dinner and then walk a few steps to a meal that’s absolutely worthy of being one of the main events of your stay.
Oakes & Evelyn Comes to Woodstock
If the Oakes & Evelyn name sounds familiar, you may already know the original restaurant on State Street in downtown Montpelier. Chef Justin Dain and his wife, Kristen, opened that location in 2021, and it developed a following for modern farm-to-table cooking that takes Vermont and New England ingredients in some unexpected directions. When the opportunity arose to open a second restaurant inside The Jackson, it gave the team a chance to bring the concept to one of Vermont’s most popular year-round destinations.
The Woodstock location opened in June 2025 and serves breakfast daily along with dinner Tuesday through Saturday. While the restaurant shares the Oakes & Evelyn name and philosophy with Montpelier, this isn’t simply a carbon copy of the original restaurant dropped into another town. The Woodstock menu has its own dishes and evolves throughout the seasons, with local ingredients determining much of what you’ll find when you sit down.
That seasonality is important because some of the dishes I loved during my summer visit may not be on the menu when you go. Rather than treating that as a downside, I’d consider it part of the reason to return.
Start With a Cocktail at the Bar
Before heading into the main dining room, start your evening with a drink at the bar.
The Jackson’s renovation created more space for guests and locals to gather, and the bar gives you a separate place to begin the night rather than immediately sitting down at your dinner table. It’s exactly how I like to approach a restaurant like this: arrive a little early, order something interesting and let dinner become the evening rather than something squeezed between other plans.
During my visit, the cocktail list was every bit as creative as the food. The Chipilos Garden combined beeswax-washed gin, mezcal, snap pea, mint and lime, while Rain Dance paired mezcal with ginger, elderflower, hibiscus and lime.
Both were a good introduction to what was coming from the kitchen because they had the same quality I found throughout the meal: familiar ingredients paired in ways that were a little unexpected without becoming complicated just for the sake of being complicated.
The cocktail menu changes too, so consider those examples of what I experienced rather than drinks I’d expect to find on the menu forever.
The Dining Room Is Part of the Experience
From the bar, head into a dining room that feels completely suited to Woodstock.
The space is light and airy, with large windows looking toward The Jackson’s grounds and a stone fireplace that becomes a natural focal point when Vermont moves into its colder months. The Jackson itself sits on more than three acres, so despite being only a short distance from the center of Woodstock, the restaurant feels removed from the activity of the village.
It strikes a nice balance between fine dining and a space where you actually want to settle in for a couple of hours. The dishes are polished and beautifully presented, but the overall experience doesn’t feel overly formal.
And then the food starts arriving.
Start With the Bao Buns
Oakes & Evelyn’s bao buns have become something of a signature, and I’d make room for at least one.
During my summer dinner, that meant a pork belly bao bun with yuzu mayo, chili crisp, pickled carrot and daikon, and cilantro. It’s technically a small bite, but there was so much happening in it: rich pork belly, the soft bao, heat from the chili crisp and enough acidity from the pickled vegetables to balance everything out.
The exact bao changes with the menu. The current Woodstock dinner menu, for example, features both a crispy sweet-and-sour chicken bao and a local mushroom version with crispy shallots, fresh truffles and kewpie.
My advice is simpler than trying to predict which one will be there when you visit: if there’s a bao bun on the menu, order it.
Local Ingredients Without Predictable Farm-to-Table Food
“Farm-to-table” gets used so often in Vermont that it can start to lose some of its meaning, but Oakes & Evelyn’s approach is more interesting than simply putting local vegetables beside a piece of meat and calling it a day.
The restaurant describes its philosophy as putting New England ingredients first while drawing inspiration from the region’s local culture and farms. The menu changes throughout the seasons as those ingredients change, but the kitchen isn’t afraid to combine them with flavors and techniques from much farther away.
That was especially apparent in the local burrata I had during my summer visit, served with a marinated tomato and cucumber salad, pistachio pesto, mint, basil and grilled sourdough. It was the kind of dish I want in Vermont in the middle of summer, when tomatoes and herbs don’t need much help, but the pistachio pesto gave it enough of a twist to make it memorable.
The current cooler-weather menu looks completely different, with dishes like stracciatella and roasted butternut squash, house gnocchi with local mushrooms, warm Vermont Creamery St. Albans cheese and chicken sausage agnolotti with butternut squash, kale, apple gastrique and fried sage.
That’s exactly what I want from a seasonal Vermont restaurant. I don’t necessarily want the same plate in January that I had in July.
The Jonah Crab and Watermelon Salad Was My Standout
Of everything I ate, there was one dish I kept thinking about afterward.
The Jonah crab and watermelon salad.
It combined sweet crab and watermelon with Castelvetrano olives, citrus vinaigrette, basil and togarashi, and it was easily my standout of the meal. The watermelon made it light and summery, the crab added richness without making it heavy, and the olives brought enough saltiness to pull the whole thing together.
This is also the dish that best captures why I liked Oakes & Evelyn so much. Nothing about it screamed “Vermont farm-to-table restaurant,” and yet it felt exactly right for a summer dinner in Vermont, using seasonal ingredients to make something creative rather than leaning on the same combinations you’ve probably eaten at a dozen other restaurants.
I would order it again tomorrow if it were still on the menu.
But since Oakes & Evelyn’s menus evolve with the seasons, I’m equally interested in seeing what takes its place.
Don’t Miss the Vermont Pork
For my larger plate, the grilled Vermont pork chop arrived with salt-and-vinegar crispy potatoes, apple and fennel slaw, chimichurri and Calabrian chile relish.
The pork was excellent. But those potatoes.
They were crispy, salty, tangy and exactly the kind of side dish you find yourself stealing from someone else’s plate after you’ve supposedly finished eating.
Again, the current menu has moved on with the season. At the time of writing, the Woodstock restaurant is serving a crispy local pork schnitzel with radicchio, Castelvetrano olives, fennel and a dill and Calabrian chile crema, alongside other large plates including a local New York strip, wild salmon and house gnocchi.
The specifics may change between making your reservation and sitting down for dinner, but local ingredients and creative combinations remain the common thread.
Stay at The Jackson and Walk Down to Dinner
You don’t have to stay at The Jackson to eat at Oakes & Evelyn, but I think pairing the two makes the experience even better.
The Jackson is a boutique Woodstock hotel with a mix of rooms and suites, set on three acres just outside the heart of the village. The property has been renovated while retaining the character of its 19th-century roots, and having Oakes & Evelyn downstairs means you can make dinner part of the stay instead of figuring out where you’re driving afterward.
I’m a big believer in this kind of travel whenever I can find it. Check into a beautiful Vermont inn, put the car keys away, get ready for dinner without watching the clock and walk downstairs for cocktails and a meal you actually planned the evening around.
After dinner, you’re heading back to your room rather than back onto the road.
For a romantic Woodstock weekend, that alone moves The Jackson higher on my list of places to stay.
Come Back for Breakfast
There’s another advantage to staying here: Oakes & Evelyn also handles breakfast.
Unlike dinner, which is currently served Tuesday through Saturday, breakfast is offered daily from 7:30 to 10:30 a.m. The current breakfast menu includes everything from buttermilk pancakes with Vermont maple syrup and a full Woodstock breakfast to an Oakes & Evelyn breakfast sandwich with Vermont cheddar and a Jackson omelette with smoked bacon and Boursin.
So yes, you can walk downstairs for dinner, head back to your room and do the whole thing again for breakfast. That’s my kind of hotel amenity.
Make It Part of a Woodstock Getaway
Oakes & Evelyn is close enough to Woodstock Village that I’d build it into a larger weekend rather than coming only for dinner.
Spend the afternoon exploring the village, walk around the Green, browse the shops along Central and Elm streets or head out toward Billings Farm & Museum. You can drive through the Taftsville Covered Bridge, explore Quechee or spend part of the day hiking before returning to The Jackson to get ready for dinner.
In fall, you have some of Vermont’s most popular foliage roads surrounding you. Winter brings skiing and snowshoeing within easy reach, while summer is ideal for hiking, farm visits and long afternoons exploring the Upper Valley.
Whatever else you’re doing, though, I wouldn’t overbook the evening.
Make the reservation. Have the cocktail. Order more than one small plate. Let dinner take its time.
What to Know Before Visiting Oakes & Evelyn in Woodstock
Oakes & Evelyn is located inside The Jackson at 43 Senior Lane in Woodstock, Vermont. The restaurant currently serves breakfast daily from 7:30 to 10:30 a.m., with dinner from 5 to 9 p.m. Tuesday through Saturday.
Because the menu changes seasonally, don’t arrive expecting the exact dishes I had during my summer visit. Instead, I’d use them as a good indication of the restaurant’s style: local ingredients, beautifully composed plates and enough unexpected flavor combinations to keep dinner interesting.
Reservations are available through Oakes & Evelyn, and I’d make one in advance if you’re planning a Woodstock weekend, particularly during foliage season, holidays or other busy travel periods.
Is Oakes & Evelyn Worth Adding to Your Woodstock Trip?
This was one of the best meals I’ve had in Vermont in some time, and what I liked most was that the experience delivered beyond simply putting beautiful food on the table.
The cocktails were creative, the dining room was gorgeous without feeling stuffy, the menu made genuinely interesting use of local and seasonal ingredients, and dishes like the Jonah crab and watermelon salad gave me something I hadn’t eaten at five other Vermont restaurants already.
Add in the fact that you can stay upstairs at The Jackson, walk down for cocktails and dinner, and wake up to breakfast from the same kitchen the next morning, and this becomes more than another restaurant reservation.
If you’re looking for a romantic Woodstock stay built around a really good meal, I’d put Oakes & Evelyn and The Jackson on your list.
And if that Jonah crab and watermelon salad ever makes another appearance on the summer menu, order it for me.
Talk with locals
Comments
Be the first to chime in
Been here? Your tip could save the next visitor a wrong turn.