Experience Keuka in Full Fall Splendor

Penny Carlton • September 12, 2025

Celebrating Roots, Community, and Fall


Autumn brings a whole new adventure to Keuka and its surrounding communities. The nip in the air is like a gentle tap on the shoulder, reminding you to pause and notice the season turning. It slips in quietly, carrying that mix of crispness and comfort. There’s a freshness to it, almost like the world is taking a deep breath after the heat of summer. You catch the scent of drying leaves, maybe a hint of woodsmoke curling from a neighbor’s chimney, and it feels like the season is wrapping the town in a quilt of coziness. That little bite in the breeze isn’t harsh—it’s an invitation to linger over a mug of cider, to take a walk under the trees, to savor the slowing rhythm of autumn.


Take a drive on the knolls just above Keuka and you’ll find yourself surrounded by the very essence of fall. The air is sweet and full, carrying the mouthwatering aroma of grapes ripening in the vineyards and apples hanging heavy in the orchards, waiting for careful hands to gather them in. Windows rolled down, you can almost taste the season in each breath. Along the roadside, the trees have begun their annual performance, slipping into their autumn gowns of crimson, amber, and gold. Their leaves rustle and sway with the gentle breeze, as if whispering that change is here, but in the most beautiful way.  


At the heart of fall, the festivals arrive like a celebration written in color and scent. The streets come alive with rows of local artisans, their tables spread with handcrafted treasures—woven baskets, pottery still smelling faintly of clay, candles poured with care, and autumn soaps that will lather with the whisper of timeless tales. Everything seems to  tell stories of home. Everywhere you look, pumpkins crowd together, some round and plump, others tall and lopsided, each one with its own character waiting to be chosen. Mums line the walkways in bursts of amber, burgundy, and gold, their petals glowing like tiny suns against the crisp air. And then there are the harvest stands, heavy with the season’s bounty—apples that shine like jewels, jars of honey catching the light, and vegetables stacked in abundance. Laughter drifts through the crowd, and the air itself seems stitched with warmth, even as the breeze carries that familiar autumn nip. A fall festival isn’t just an event—it’s a gathering of season, spirit, and community, woven together under the glow of changing leaves.


Numerous fall festivals are coming up over the next couple months in the communities around Keuka. I’ve provided a list of a few September Festivals below (and apologies to any event I missed!) Note to vendors: Some of the Festivals listed below are still taking vendor applications, so check out their FB page.


With a pumpkin latte in hand, I invite you to mark your September calendars, gather up some family and friends and fall in love with Keuka this fall! (And watch for the October list of events coming at the end of September!


Glenn H Curtiss Museum’s Wings and Wheels Seaplane and Car Show

September 13th Starts at 9:00 AM

Depot Park, Hammondsport, NY


Heron Hill Winery Fall Festival

September 13th 1:00 – 4:00 PM

9301 County Route 76, Hammondsport, NY


Hammondsport Heritage Day Presented by Fred & Harriett Taylor Memorial Library

Sept 20th from 11:00 AM to 1:00 PM

21 William St, Hammondsport, NY


Fall Car Show at The Windmill

September 20th 8:00 AM – 3:00 PM

3900 New York 14A, Penn Yan, NY


Fall Festival at LWL Gift Shop

September 27th 10:00 AM – 4:00 PM

161 County Route 23, 14815-9724


·The Greater Hammondsport Chamber of Commerce Octoberfest

 September 27th 1:00 PM – 5:00 PM

Hammondsport Fireman’s Pavillion, Hammpndsport, NY




 

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“When gratitude turns into giving, a community shines brighter.” As I was scrolling through Facebook last night, I came across a post from Lauren McQuaid, owner of Simplicity on Main , that truly touched my heart. Her words carried such warmth, gratitude, and purpose that I felt compelled to share them — not only to help her spread the word, but to celebrate the kindness that makes our community so special. There’s a quiet kind of beauty in kindness — the kind that radiates from people who use what they have to make the world just a little bit better. Here in Penn Yan, that beauty shines brightly through Lauren McQuaid, owner of Simplicity on Main, a women’s clothing boutique that has become more than just a place to shop. It’s a space where confidence, connection, and community come together — and this season, Lauren is weaving those values into something even more meaningful. A Giving Spirit Lauren believes in gratitude in action. As she says so simply, “ When you’ve been blessed with a large platform, you need to do as much good with it as possible.” With the holidays fast approaching — a time of joy, reflection, and often, struggle — Lauren wanted to find a way to lift up those in need right here in Penn Yan. Over the next several weeks, Simplicity on Main will be collecting unexpired pantry goods for a local charity that serves families in our own community. Anyone wishing to donate can drop items off during the boutique’s regular business hours. And, as a sweet token of appreciation, the first 25 people who contribute will receive a small thank-you gift from Lauren and her team — a gesture that reflects the generosity and heart that define her shop. Style with Purpose Since opening her doors, Lauren has created more than a boutique — she’s created a gathering place. A place where women come not only to find beautiful clothes, but to feel seen, celebrated, and encouraged. Her belief that “nobody should ever go without” extends far beyond fashion; it’s woven into the very fabric of her business. Whether it’s through a smile, a compliment, or this latest community project, Lauren continues to remind us that style isn’t just about what we wear — it’s about how we show up for one another. The Heart of Penn Yan Penn Yan’s charm comes from its people — the small business owners, volunteers, and everyday neighbors who quietly make a difference. Lauren’s giving initiative is one more reason our visitors often say, “You can feel something special here.” It’s true — in our little village, kindness isn’t rare. It’s part of who we are. So as you stroll down Main Street this season, stop into Simplicity on Main. Browse the racks, say hello, and if you can, drop off a donation. Because when we come together — one can, one act of kindness, one heart at a time — we make Penn Yan shine just a little brighter. ❤️ Thank you, Lauren, for reminding us what it means to lead with grace, gratitude, and community spirit. 🛍️ Visit Simplicity on Main Let’s do what we do best, Penn Yan! ❤️ Weekly Hours: Monday: 9 AM – 3 PM Tuesday: Closed Wednesday: 9 AM – 3 PM Thursday: 9 AM – 3 PM Friday: 9 AM – 5 PM Saturday: 10 AM – 3 PM Sunday: Closed Address: 📍 1 E Main Street, Penn Yan, NY (The old bookstore on the corner of Main and Water St!) Join Lauren and Simplicity on Main on FB
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