An Evening of Connection at Silas House and the Magic of Asking

On a soft, cool Catskills evening this late spring, a group of local entrepreneurs, creatives, and community builders gathered for an intimate multi-course dinner in the beautifully reimagined barn at Silas House. Hosted by proprietors Natalie and Aldo, the husband-and-wife team warmly greeted each guest who stepped into the broad, inviting space—equal parts rustic and refined, offering a cozy backdrop for a seasonal feast by celebrated Hudson Valley Chef Deanna D’Angelo.

Guests sipped local wine and caught up on news or made introductions as they played a lazy game of pool or made rounds to the abundant hors d’oeuvres table: French triple cream with fresh blackberries, roasted garlic, Skytop Springs smoked trout with capers and lemon, Hudson Valley duck breast, charcuterie, farm-fresh cheeses, Bramley Mt. Farm meatballs, and antipasti. More introductions were made, and the happy din of chatter grew louder in the room. 

The last of the sun had slipped behind the mountains.  At the long wooden farm table, the first course arrived—a riot of color and flavor: organic spicy greens, roasted shallots, and drunken grapes sweetened with local honey and crowned with edible flowers. Though the gathering was the brainchild of Natalie and Aldo as a way to foster local community, the evening’s format was offered in collaboration with Terry Dagrosa, Editor/Creative Director of INSIDE+OUT, and me, Content Director of INSIDE+OUT and founder of Crescent Hudson Valley, a community well in Gardiner, NY. All of us are similarly driven to deepen the connections and experiences across the Hudson Valley. 

“There is no such thing as a stranger—just someone whose story you haven’t heard yet.” (-Quote unknown.)

Together, we introduced guests to the format: the Ask Me Anything Dinner. Designed to cultivate open-hearted conversation, the experience invites deeper dialogue and a stronger sense of connection, even among strangers. 

The guidelines are simple:

• Questions—focused around a preselected theme (in this case, Spring Renewal in the Valley)—are drawn from a basket. Some are playful, others disarmingly personal.
• One person draws a question out of the basket. They have the option to answer if it sparks a story or pass. 
• The first person can then draw another question, answer or pass again. 
• One person speaks at a time, from the heart. 
• Everyone listens, also from the heart.
• Be mindful of time and speak “lean.”
• All answered shared in the circle stay in the circle.

The “Ask Me Anything” format was inspired by Indigenous communication practices and The Way of Council, a method introduced by Jack Zimmerman and used across cultures, even in conflict resolution. As I told the group, “There is no such thing as a stranger—just someone whose story you haven’t heard yet.” (-Quote unknown.)

A smiling Chef Deanna had her own stories to share about the origin of the menu’s inspiration and ingredients; each course was a love letter to the land and the season. As she and her team plated each course—including Hudson Valley filet mignon with whipped garlic potatoes, asparagus, and red pepper ragout—guests were drawn deeper into the meal and one another’s company. Dessert came in the form of a dreamy San Sebastian cheesecake crowned with drunken cherries. 

Community building is on many people’s minds lately, especially in the Hudson Valley, as a way to counterbalance the isolation, division and digital overwhelm so many are experiencing. Most at the table that night were local entrepreneurs, artists, and change-makers, genuinely invested in their neighbors’ well-being and the vitality of the region. That includes the quality of the water, air, and soil, as well as a healthy future for our children and the creatures with whom we share these beautiful mountains. 

As forks and glasses hovered midair, the room often fell into attentive stillness, only to erupt moments later in knowing laughter or spontaneous applause as we took turns answering questions—about gardening rituals, springtime memories, getting caught in the rain, or our dream dinner guests from history—the room oscillated between laughter and attentive stillness. No phones. No clamor, no world’s bad news. Just the rare delight of presence and commonality in spite of things.

In a small barn in Upstate New York, 15 guests were reminded that we’re not strangers at all. With each round of stories, our inner wilds and memories bloomed a little more. Of barefoot childhoods, family picnics gone awry, missed spring flowers, favorite Catskill activities, and cherished rituals with family and friends. There were also small quips of delight as guests took petit tours of the Inn, reemerging at the table to gush about the fresh decor and delightful details.

In the end, the consensus was clear: Silas House offered extraordinary hospitality. Chef Deanna and her “fleet of pasta-making ancestors” should definitely keep on cooking. And the Ask Me Anything format? It gave people permission to be real. Through deeper sharing, listening, and spontaneity, unexpected friendships formed or deepened thanks to reflections on the pure joy of ramps and morels, dreams realized here in the mountains, and the shared love of soil among lifelong locals and recent transplants alike. 

By the time the last plates were cleared, what had begun as a dinner had become something else entirely. Not a ceremony, exactly. Not performance. But something rooted and alive needed nourishment of a different kind. Recipes were exchanged. So were phone numbers. And there were hugs and promises of more to come.

A special shout-out to the guests…

Sal Fabbella at Catskill Outpost | Instagram

Steve + Marcy at Sticky Petal Farm | Instagram

Caitlin + Will (Owners) Van Dusen’s General Store | Instagram

Matt + Melissa Peters at What The Soap | Instagram

CREDITS

As Me Anything Dinner by Jenny Wonderling at Crescent HV | Gardiner NY |  Instagram 

Pop Up Dinner by Chef Deanna + Owner of Bramble Hill | Bovina NY | Instagram

Flowers by Sticky Petal Farm  | Jefferson NY | Instagram

Photography by Mia Lile | Instagram 

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Follow/Connect with Silas House via Website | Facebook | Instagram | Inside+Out Spotlight

Book a room or event at Silas House.

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Want to host an Ask Me Anything Dinner? 

Contact Jenny Wonderling HERE.

Mark your calendar: The next Ask Me Anything Dinners are scheduled for August 9th + August 23rd, 2025, at Crescent Farm in Gardiner, NY, in collaboration with INSIDE+OUT.

In case you missed it, read more about INSIDE+OUT’s “Ask Me Anything Dinner With Chef Marion Maur.”