Come here with your twin toddlers, your 98-year-old grandma, or your punk band, and you’ll be coddled and fed like family—a genuine Woodstock welcome.
With its warm, inclusive, and vibrant atmosphere, Oriole 9 in Woodstock is as pleasing to the soul as it is to the senses. All are welcome at this bustling eatery in the center of town, and are sure to be delighted by the comfort-meets-eclectic cuisine, lovingly prepared and lovingly served.
That’s the standard set by owner Jessica Anna, and she’s constantly raising the bar: come here with your twin toddlers, your 98-year-old grandma, or your punk band, and you’ll be coddled and fed like family—a genuine Woodstock welcome.
Jessica is as genuine and as Woodstock as it gets. “I grew up here,” she says. “I spent time in L.A. and New York, but I’ve basically been here all my life, and I’ve been working in the restaurant scene since I was 14 years old. I love the mountains, the lakes, the people.” Like many Woodstockers, she has a creative background.
“I come from an arts family—my grandmother and mom were artists, my dad a jeweler.” During her rare free time, she likes to paint, but most days her creativity is channeled through serving people amazing food.
“A fun thing that we do is Make Your Own Mimosa. We set you up with a bottle of Prosecco and a couple of juices—freshly squeezed OJ, peach puree, blueberry lavender—and you can customize.”–Jessica Anna, owner
Jessica was always powerfully drawn to food and hospitality; she’s worked in some of Woodstock’s most enduring establishments: the Bear Cafe, Sunfrost, Heaven (now closed), and Joshua’s. “I love food and I love the business. I love serving people and hostessing parties—all of it. I love taking care of people.” She’s also quite fond of the town. “This is such an incredible community. People look out for each other, have each other’s back—just make a wonderful life together. I’m still friends with people I went to preschool with.”
As a young woman, Jessica earned a psych degree and taught for a time, mulling a career as a therapist, but the kitchen was calling her back. “I missed restaurants,” she says of that time. So when Oriole 9—which derived its name from the old Woodstock telephone exchange—first opened twelve years ago, she and her husband Chris got involved. At first it was an investment, but it grew into a labor of love, and when two other partners stepped aside three years ago, Jessica stepped up as operating manager. “It’s been interesting; one thing I didn’t realize was how much I would enjoy the business side of the operation, the bookkeeping and organization,” she says.
“It’s actually fun.” But nothing’s more fun than feeding people, and she enjoys the creative challenge of keeping the menu fresh and unique. “We have old classic favorites, things I love: avocado toast with arugula truffle oil and poached egg, quesadillas with fire roasted poblano peppers, our Catsmo smoked salmon bagel, our grilled Reuben and veggie tempeh Reuben,” she says. “It can be hard to change the menu when you have things people love. I hear, ‘Oh, you’re my favorite restaurant!’ a lot. I so love hearing that. I never want that to change. But I do like to stay current and innovate. Lately I’m loving shakshuka, a dish with eggs poached in tomato, chili peppers, onion, spices like cumin.... It originated in Tunisia, and I just did Ancestry.com and found I have a tiny bit of Tunisian in me,” she says with a smile.
Only the best local ingredients are used in the exquisite preparation of Oriole 9’s dishes, which is another secret to their success. “Eggs, milk, produce, coffee, beer, wine, cider—there are so many wonderful local producers to work with nearby,” Jessica says.
The restaurant’s location—just off the Village Green in Woodstock—plays an important role in keeping the vibe interesting, and keeping the restaurant connected to the community. “It’s perfect, right in the center of things.
I wish we had windows on the street and outdoor seating, but we’re doing fine; it’s a beautiful space in just the right spot. And I love the central Woodstock restaurant community. The restaurants in the center of town are all owned and operated by women, and we’re all friends; if one place runs out of something, they run to another place and borrow some. It’s a genuine, giving community spirit, and I’m really happy to be part of it.”
Both Jessica and the restaurant thrive on the Woodstock crowd. “We get locals, we get people passing through, we get people from the city—families, celebrities, all ages. People see the buzz on social media or hear about us and try us out, and then it’s our job to maintain the consistency and quality that keeps them coming back.”
The newly renovated dining room—with all-new colors, new floors, and a small bar (“People can watch their hand-pulled coffee being made now!”)—will still be decorated with works by local artists.
“Showcasing local art is super important to me. I base it solely on quality and change the show about every other month or so. It’s fluid. I fall in love with stuff and don’t want it to leave. I still have a Lenny Kislin piece up. But it’s great to be able to offer select artists a venue where, on a busy summer week, 1,000 people may see their work.” Equally important to Jessica is her crew. “My staff call me Mama Bear. We’re like a family of friends; a lot of us have been working together for 10 years. We treat one another well and have fun and take good care of the customers. I have such a good crew now that I can step out and do some front-of-the-house work and public relations, which I love—but then, I love cooking too.”
“I’m in this for people. For the community, and the spirit of it all.”
Being an independent entrepreneur is a scramble, especially in the competitive world of food in a busy tourist town. “When I took over, our kids were eighteen months, nine, and fifteen, if you can picture that. Chris is a partner, but he’s got his own contracting business. I’m so lucky to have a solid staff. Winters can be hard, too; you scrape by and work extra hard to make up for it in summer and fall.”
But the joy prevails, and Jessica’s always thinking up a new twist. “A fun thing that we do is Make Your Own Mimosa. We set you up with a bottle of Prosecco and a couple of juices—freshly squeezed OJ, peach puree, blueberry lavender—and you can customize. We have just a beer and wine license, but the beer and wine are top-notch.”
This June, Oriole 9 is celebrating its 12th birthday—something to be proud of, indeed. “We’ll be rolling out our new summer menu—you’ll be able to find that on Facebook and Instagram,” says Jessica.
Whether it’s breakfast, brunch, or a darn good cup of coffee you seek, let Oriole 9 be your launch pad for a day of exploring Woodstock. Or bring the kids for a fun family lunch—they’re always welcome. You can be sure Mama Bear will take good care of you. “I am so grateful, each and every day, for my staff and my customers and supporters,” she says. “I’m in this for people. For the community, and the spirit of it all.”
17 Tinker Street, Woodstock