In June 2025, Justin Dain, owner and chef at Oakes & Evelyn in Montpelier, opened a second location by taking over the dining room of The Jackson. (The new spot retains the same name. Thomas Oakes was Justin’s grandfather, and Evelyn Garbe was his great-aunt.) Justin had been contemplating opening an additional restaurant when he was approached by the hotel owners. “The timing, the location . . . everything seemed to align,” Justin says, and it dovetailed with his own professional desire to “stay creative and do new things.” Hotels are a familiar milieu. Justin has commanded the kitchens at the Boston Harbor Hotel, Reluctant Panther Inn and Restaurant in Manchester Village, Vermont, and before opening his Montpelier restaurant in 2021, he had been the executive chef at the Hanover Inn in Hanover, New Hampshire.

 

Local, Seasonal Dishes

If you have dined at Oakes & Evelyn in Montpelier, the experience at the Woodstock location feels and tastes familiar. Both restaurants source from local purveyors like Black River Produce in North Springfield, Vermont, for meats, fish, and vegetables; proximity to Boston and Cape Cod guarantees fresh oysters. What’s on your plate could also come from Oakes & Evelyn’s own vegetable gardens.

The menus change with the seasons, and while they bear a resemblance to one another with a mixture of small and large plates, they are not identical. Each Oakes & Evelyn has a few unique dishes. Both, however, offer several dishes of crudo, sophisticated raw seafood such as Hamachi Crudo with aji amorillo and coconut sauce, peanuts, Szechuan oil, and cilantro. The crudo is a part of the menu that sets Oakes & Evelyn apart. Justin explains that while working in Boston he developed an interest in raw fish, its seasonal nature, and the creativity involved in its different preparations.

Previous patrons of the former restaurant at The Jackson may remember the commanding fireplace that still anchors one end of the dining room, a pleasant space with a herringbone wood floor and at the other end, large windows with a view of the landscaped gardens. Whether because of its history, the spaced tables, or the white tablecloths (which may be temporary, Justin believes, once they are able to improve the sound quality in the room), this new Oakes & Evelyn has a bit more of a New England upscale vibe.

 

Food That Speaks for Itself

Asked what changes he has seen over his years as a chef, Justin says, “technique . . . and simpler is better.” Gone are the days of gels and foams on overdone plates. Flavor is still key; fussiness is not. On its website, the restaurant promises to

“ . . . put the ingredients first and execute them to the highest degree to make the local food shine and speak for itself.”

As for clientele, their needs and requests have evolved over time too. Whether because of religious or health reasons, or simple preference, there is more of a demand for vegetarian and vegan items on the menu. Justin tries to keep a number of those offerings available. And patrons are increasingly diverse. Montpelier has courted and serves primarily a local clientele. Because of the timing of the opening and the location, Oakes & Evelyn in Woodstock has been serving tourists from everywhere, although as the word has spread, local folks are becoming more frequent.

The talents of a team in each kitchen and a front-of-the-house staff are essential to the success of Oakes & Evelyn. At a time when many restaurants and local businesses are facing an inability to recruit and retain staff, Justin says that opening a new restaurant in Woodstock presented challenges, at least in the beginning. Oakes & Evelyn advertised for staff through traditional advertising and social media. Word of mouth proved essential. According to Justin, having “happy employees and a happy place to work” is one of the rewards of owning and running a restaurant. He is a believer in working alongside his staff and leading by example.

A Labor of Love

Justin, who lives with his family in Grantham, New Hampshire, puts considerable mileage on his car as he pings from home to one or the other—and sometimes both—restaurants. For the moment, Oakes & Evelyn at The Jackson is garnering more of his attention since it’s newer; his team in Montpelier is experienced and adept at keeping things running smoothly. And this second Oakes & Evelyn is serving not just dinner but also breakfast to hotel guests and the general public, which means that the chef may start and end each day there.

His own biggest challenge? “It has to be work-life balance.” With two restaurants approximately 60 miles apart from one another, and 60- to 70-hour work weeks spent on the road or on the job, keeping everyone happy is a day-to-day feat.

What makes the long hours worthwhile? In addition to creating a happy workplace, chefs love to feed people. Justin sees Oakes & Evelyn—in either location—as a “home for the community to come in and just have a great night.”

 

RECIPE

Pumpkin Gnocchi with Kale, Wild Mushrooms, Bacon, and Sage

1 qt water

1 lb unsalted butter

Salt to taste

20 oz all-purpose flour

1 cup Parmesan cheese (grated)

8 oz pumpkin puree

14 eggs

4 egg yolks

¼ lb slab bacon

1 oz canola oil

1/4 cup wild mushrooms

1/2 cup chopped Tuscan kale

1 tsp chopped sage

2 oz vegetable stock

1 Tbsp unsalted butter

2 Tbsp pecorino cheese

Chives to garnish

 

1.) Bring water, butter, and salt to a boil. Add flour and stir until fully incorporated.

2.)  Place mixture in a stand mixer with the paddle attachment. Add Parmesan cheese and pumpkin puree and mix for 20 seconds. Slowly add the eggs and egg yolks one at a time.

3.) Place mixture in a piping bag with a large plain tip. Pipe small amounts of the mixture into salted simmering water for 1 minute and then shock the gnocchi in an ice bath. Reserve the gnocchi.

4.) Dice the slab bacon into small dice and slowly render in a sauté pan on low to medium heat until crispy. Cool and reserve.

5.) In a sauté pan over medium heat, add the canola oil and the wild mushrooms and cook until they begin to caramelize. Add a tablespoon of crispy bacon, kale, and chopped sage to the pan and cook until the kale has wilted.

6 .) Add a cup of gnocchi to the pan with the vegetable stock and bring to a simmer. Once the stock is reduced by half, add the butter and pecorino cheese. Garnish with chives.

 

Oakes & Evelyn

43 Senior Lane

Woodstock, VT

(802) 272-7007

oakesandevelyn.com/jackson