Around the table: 4 entertaining insights from entrepreneur Sas Stewart

Ideas on gathering well from the founder of Adventure Dinner

When Sas Stewart was looking to get the word out about her recently launched line of spirits in her new community of Middlebury, Vermont, she knew she’d have her work cut out for her. What she didn’t anticipate was the sheer amount of creative force she’d find in just one place. “I was meeting florists, graphic designers, photographers, chefs and farmers, and thought to myself, ‘What if we created an experience where people could get to know not just one singular entity, but many of them at once?’” she says.

Photo: Adventure Dinner / Daniel Schechner

Thus was born Adventure Dinner, a speakeasy supper series that pops up in unexpected places throughout Vermont with a mission of highlighting the state’s chefs, makers and producers. “We want to tell the stories of both place and people through these experiences,” notes Stewart. The series began in 2014, when guests kicked off an evening with a cocktail cruise across Lake Champlain to a remote rock outcropping. There, they were met by two local chefs who served multiple courses over an open fire as the sun went down.

It was just the beginning. The team has hosted dozens of Adventure Dinners since, each one making its mark on a new space and collection of talent. And while every event is a special one for Stewart—from a Bridgerton-inspired tea and foraging walk to a Point Break-themed beach party— these gatherings always come back to the people. Here, Stewart shares four core insights on new ways we can understand and enjoy the gathering.

“This series really came about as a way of bringing people together for a new kind of gathering—that has been our biggest goal.”


Rethink the why, when and what


Photo: Adventure Dinner / Carey Nershi

Stewart notes that the past year has given us a pause to reflect on an always-central question: why we are choosing to gather in the first place. “We may have previously taken for granted the fact that we could gather, and this is an opportunity for us all to consider when we gather, and the biggest reason behind why we do. Most likely, it’s not going to be that you nailed the cooking temp for your appetizer—it’s going to be the chance to bring together people you care about.” In addition to the “when” and the “why,” Stewart suggests a third “W” regarding celebrations: the what.

“Women often get stuck in the regimen of celebrating only the ‘three Bs’—birthdays, bridal showers and babies—and I think we can really expand on that,” says Stewart, who notes an array of other life events that can be celebrated—not just for women, but for all participants. That includes everything from promotions to times one has overcome challenges, to hyper-specific happenings, such as the joy found in discovering a new exhibit or restaurant that you want to share with others.

“We can really build on our definition of what is worthy of celebrating, and what is worthy of gathering around.”


Join forces


Photo: Ellison Estate Winery

Stewart credits the success of Adventure Dinner to collaboration, and she finds the same to be true for other gatherings, too. “When we host a get-together, too often we feel that we have to be immaculate, we have to do everything, and that it’s on us to achieve perfection—and I think that type of thinking is unrealistic and toxic,” she says. Rather, she suggests teaming up with your guests, not just to remove event stress, but also as a way of inviting guests in for a way of gathering that feels intentional. “I believe that at the core of coming together, everyone wants guidance—we want to understand what our role is at an event or in a space,” she says.

Photo: Adventure Dinner / Chadwick Estey

One of her favorite host formulas? One person brings the flowers, another person the drinks, two people bring courses, another brings table and settings and—here’s a novel one—someone chooses the location. “Maybe it’s not where you typically would host a dinner, but they pick it, and we roll with it,” Stewart notes. “And here’s my guess—it will be one of the most memorable dinner parties you and your group have—not because it’s the right food or the right flowers—but because everyone worked together to create something special.”


“We want to tell the stories of both place and people through these experiences.”


Challenge the ordinary, by putting people first


Photo: Adventure Dinner / Kevin King

When it comes to plans, Stewart has found that there is often more fun—and more opportunity for lasting connection—when certain rules are challenged. “I think you can be formal in informal settings, and informal in formal settings—so long as you know why you’re doing it,” she says, giving the example of unrolling picnic blankets at a wedding.

“A wedding is a time to bring two families together and to celebrate love—and if that’s the filter with which you make all of your decisions, then suddenly whether or not you have the right flowers or place settings doesn’t really matter as much as ensuring everyone in attendance is being honored and included—right down to the families with kids who just want a comfortable seat,” she says.

“We can choose to make people the centerpiece of our gatherings, and to build all of the delight around them.”


Cultivate comfort


Photo: Adventure Dinner / Chadwick Estey

Another benefit to shaking up the standard event protocol, Stewart notes? A nod to the fact that your hangout is tailormade. “You can cue to your guests that this is something special—that your host has curated something just for you.”

Her personal favorites? Going out of your way on greetings, and having something special to toast with. “The act of welcoming someone into the group is a crucial part of gathering. I love to organically introduce new arrivals to whomever is nearby, even if I think they know each other. Arriving can be stressful, and a little laugh over ‘Oh, of course, we’ve met before!” can be all it takes to jumpstart a genuine conversation.”

Beverages, Sas notes, can also be an easy way to engage. “I prep a tray of festive drinks and hand them to friends as they arrive—it’s a little gift they receive as soon as they walk in the door. Big note: make sure that your non-drinkers have a handcrafted selection, too (beyond just a seltzer!) It makes the evening center on conviviality, and it goes a long way in helping everyone to feel comfortable.”

Photo: Adventure Dinner / Carey Nershi

The benefits of personalization can extend far beyond an event’s hours—paving the way for connection during, and long after, a one-off gathering. “When we relax the edges of a formal event, it helps guests to feel comfortable—and comfort so often can actually mean acceptance,” says Stewart, who notes that by being thoughtful about creating an inviting space, we can enjoy the company of our guests (and ourselves) exactly as we are.


“…When we gather, we’re doing more than coming around a table—we’re creating centers of acceptance, in which we can strive to see everyone from every angle.”


This story appears in One Adventures, Berkley One’s digital magazine celebrating creators, experiences and stories. Read the issue here.

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Header Image: Adventure Dinner / Chadwick Estey.