Ten years after opening The Pines, Jeremy Bernstein said the business has become what he hoped it would be: a place where people gather for food, music, and the kind of familiarity that makes a night out feel like dinner at a friend’s house. Bernstein, 52, grew up in Woodstock and came to hospitality after years as a touring musician and woodworker. He bought the longtime former home of Tiso’s Trattoria, restored it, and built a business that has endured in a tough industry and away from a main-street location. As The Pines enters its second decade, Bernstein spoke with The Overlook about the restaurant’s evolution, the loyal local crowd that keeps it going, and why social media has become one of its most effective tools.
How did The Pines begin?
I kind of came to a place in my life where I wanted to focus and be in the same place every day and build on something, as opposed to running around the country or working on people’s homes. I wanted to do something for myself.
This place really just happened out of nowhere and kind of by chance. The building had been occupied for 55 years by one family, the Tisos, and they had Tiso’s Trattoria in it. It was a family-run Italian restaurant from 1964 to 2015. As I toured the building and looked at it, all the light bulbs and sparks went off. I love entertaining, I love food, I love wine and tequilas, and I knew that I could do lodging, I could do music, I could do food. There’s a beautiful big yard. We can host events. It seemed like, in that moment, a once-in-a-lifetime opportunity.
What did you want the business to be when you started it, and how has that vision held up?
What I’m probably most touched by and feel the accomplishment of is that everything I set out to do happened, which rarely happens in life, where you have an idea and a vision and all the parts come together.
When I was thinking of this place, I was thinking of it as my living room: come over, see a show, have some food, hang out. And it’s really become a community hub. I’ve watched several relationships grow and flourish and bloom and just happen out of never meeting someone. It kind of seems like there’s some vortex here where I’ll see people go, “Oh my God, is that you?” and they’ll bump into someone they haven’t seen in 10 years.
The music was always at the forefront for me, and luckily it happened and we’re still here. Most restaurants fail in a couple of years.
Why do you think The Pines has lasted?
I think it’s being true to the vision and the vibe, as well as dedication and hard work. I have a lot of people say to me, “I’ve never been to an establishment like yours where we see the owner every time we come.”
I think that dedication to being this kind of community gathering space, as well as the music venue, is important. We do fun things. A good friend of mine is a bingo caller. We do bingo every couple of months. Another friend runs a really fun trivia game night. I think just the fact that it’s not just a restaurant is why it survives.
The food is good. People love it. But that’s not the only reason people come here.
Social media seems to be a big part of The Pines’ identity. How important has it been?
It plays a huge part. We’ve never spent money on advertising, not once. So social media, mostly Instagram, has been huge.
I see direct results from it from time to time. I do these fun videos where I’ll eat a new dish or do those things, and it’s like, “Oh wow, that item is not really moving as much as we thought it was. I’ll do a video to show it.” And all of a sudden 12 people come in that night and buy that thing.
So yes, I see social media, for whatever it’s worth, as our biggest tool besides word of mouth.
What does your staff look like these days?
We have a very small, loyal staff. We have two cooks in the kitchen. We have a dishwasher. In the slow months, I run food and host, and in the busier months, I’ll hire someone to run food. On the floor we have a bartender and two servers. So, a very small team.
We’re like a little family. My bartender, Rachel, has been with me since the very beginning. My chef, Aiden, is now coming up on six years. Our dishwasher is coming up on five years. One of the servers has been here on and off for years and the other now three years. Everybody stays, which is really nice.
And it’s really nice for the customer base. They get to come back and see the same server and they’re like, “Oh my God, it’s Nikki, how are you?” I’m very thankful for that.
You came to this as a musician, not a restaurateur. How did music shape the way you run the place?
Being in a band is like being in a relationship of some sort. I had many years where I was a band leader, so I was the songwriter, the singer, the rhythm guitar player. I would always surround myself, luckily, with great musicians and friends.
Being a band leader is very much like being a manager. You have all these personalities to deal with and bring together. Then you have logistics. Especially when you’re on that level, there’s no tour manager. You have the skills of making phone calls, booking shows, talking to the promoters. When you get to the bar, you’ve got to deal with whoever’s managing and the sound guy. So I think there was a lot of skill gained from that, for sure.
What should people watch for this spring and summer at The Pines?
Keep an eye on our website calendar. I always love to plug our little outside bar called the Dog House. We serve beer, wine, highballs, we do hot dogs, we’ve got a bunch of toppings and different stuff. That’s a big outdoor vibe. That’s noon to 4 p.m. Saturdays and Sundays.
And then we also tend to have a lot of food pop-ups, like Oyster Party. Different people will come in with whatever’s complementary to what we’re doing. Then there’ll probably be four big barbecues a year, with live music in the field. We have a big stage in the back. Keep an eye on our events calendar for when those dates pop up.
Photos by Michael Sofronski for The Overlook.
Noah Eckstein is the editor-in-chief of The Overlook. Send correspondence to noah@theoverlooknews.com.