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Join us for our second Upstate Writing & Substack Retreat—a long weekend of storytelling, creativity, and connection, co-taught by Jessica DeFino (Fleshworld, 130K followers) and Molly Rosen (The Cut, Brooklyn Writers Collective). Set against the changing leaves of upstate New York, this immersive retreat blends creative mentorship with practical strategy to help you generate meaningful new work and build a Substack that lasts. We'll gather around fire pits and farm tables to write, read, and reconnect—fueled by good food, crisp autumn air, and the quiet magic of the season.
Each day begins slowly: breakfast, a Tiny Story Hour, and a craft lecture. From there, you'll have long stretches of open writing time—disappearing into a cozy corner to draft, explore, and follow your ideas—along with one-on-one creative ideation sessions with Molly and Jess. Afternoons bring us back together for group workshops around a long table, where we'll give and receive feedback in a space that's warm, rigorous, and alive.
Throughout the weekend, we'll move between generative writing and hands-on Substack strategy. You'll learn how to shape your voice into a compelling newsletter, from crafting irresistible subject lines and openings to designing a clean, readable format and developing a sustainable publishing rhythm. We'll cover content mix, cadence, and growth—without losing what makes your work personal, strange, and true.
The goal: to unplug, put pen to paper, and follow your curiosity until you uncover something honest—then build a platform strong enough to carry it into the world.
In between: woodland walks beneath changing leaves, afternoon naps, wandering into town, shared meals, lingering conversations, and the slow, steady intimacy of a weekend devoted to making something. Hot cider. Good snacks. Firepits. Sweaters. Star-filled autumn skies.
You'll leave with:
Clarity around your Substack strategy and voice
5+ drafted or outlined posts
A realistic, sustainable growth plan
Renewed creative energy and momentum
A community of smart, engaged writers to keep you accountable
Schedule:
November 5: 6:30–9:00 PM
November 6: 9:30 AM–5:00 PM
November 7: 9:30 AM–5:00 PM
November 8: 10:00 AM–1:00 PM
For anyone craving creative ignition, deeper focus, and a community that will push your work forward.
Space is limited.
Suggested spots to stay in town, walking distance.
Bed and Breakfast:
The Woodstock Inn on the Millstream
Hotel:
Woodstock Way (five minute walk)
Hotel Dylan (ten minute drive)
Join us for our second Upstate Writing & Substack Retreat—a long weekend of storytelling, creativity, and connection, co-taught by Jessica DeFino (Fleshworld, 130K followers) and Molly Rosen (The Cut, Brooklyn Writers Collective). Set against the changing leaves of upstate New York, this immersive retreat blends creative mentorship with practical strategy to help you generate meaningful new work and build a Substack that lasts. We'll gather around fire pits and farm tables to write, read, and reconnect—fueled by good food, crisp autumn air, and the quiet magic of the season.
Each day begins slowly: breakfast, a Tiny Story Hour, and a craft lecture. From there, you'll have long stretches of open writing time—disappearing into a cozy corner to draft, explore, and follow your ideas—along with one-on-one creative ideation sessions with Molly and Jess. Afternoons bring us back together for group workshops around a long table, where we'll give and receive feedback in a space that's warm, rigorous, and alive.
Throughout the weekend, we'll move between generative writing and hands-on Substack strategy. You'll learn how to shape your voice into a compelling newsletter, from crafting irresistible subject lines and openings to designing a clean, readable format and developing a sustainable publishing rhythm. We'll cover content mix, cadence, and growth—without losing what makes your work personal, strange, and true.
The goal: to unplug, put pen to paper, and follow your curiosity until you uncover something honest—then build a platform strong enough to carry it into the world.
In between: woodland walks beneath changing leaves, afternoon naps, wandering into town, shared meals, lingering conversations, and the slow, steady intimacy of a weekend devoted to making something. Hot cider. Good snacks. Firepits. Sweaters. Star-filled autumn skies.
You'll leave with:
Clarity around your Substack strategy and voice
5+ drafted or outlined posts
A realistic, sustainable growth plan
Renewed creative energy and momentum
A community of smart, engaged writers to keep you accountable
Schedule:
November 5: 6:30–9:00 PM
November 6: 9:30 AM–5:00 PM
November 7: 9:30 AM–5:00 PM
November 8: 10:00 AM–1:00 PM
For anyone craving creative ignition, deeper focus, and a community that will push your work forward.
Space is limited.
Suggested spots to stay in town, walking distance.
Bed and Breakfast:
The Woodstock Inn on the Millstream
Hotel:
Woodstock Way (five minute walk)
Hotel Dylan (ten minute drive)