The moment the first holiday lights begin to twinkle along Main Street, Penn Yan shifts into something almost enchanted. A single wreath catching the glow… a ribbon dancing in the breeze… a window display sparkling just so — and suddenly, the whole village feels wrapped in Christmas charm.
I got it from some of Santa’s little elves, Christmas shopping on Main Street this year promises to be one of the most delightful ones yet. On November 22–23, downtown transforms into a festive walkway filled with warmth, cheer, and that unmistakable small-town magic that makes Penn Yan feel like it stepped straight out of a classic holiday Christmas movie.
Stroll down Main Street and you’ll find shops dressed in their holiday finest — evergreen trails, shining ornaments, flickering candles, and displays that beckon you to wander, linger, and discover something special.
π Three Beloved Holiday Open Houses to Begin Your Journey
β¨ Long’s Cards & Books — Annual Christmas Open House
A Penn Yan tradition that feels like coming home.
Step inside and you’ll be welcomed by the scent of cinnamon, the sound of festive music, and familiar smiles that warm you instantly. Christmas treasures are tucked around every corner — books, ornaments, décor, and nostalgic gifts that light up the heart. Long’s wraps the season in comfort, wonder, and memories waiting to be made.
π The Nest Egg — Holiday Open House
Where cozy charm and small-town magic meet.
Twinkling lights, beautifully curated displays, handmade finds, and home décor fill every nook. The Nest Egg’s Christmas Open House is the kind of place where inspiration flows and holiday cheer lingers long after you leave.
πΆ A little elf just popped in with a last-minute hint…
Dave Boyd’s Music is hosting an Open House this weekend too! And oh, the melodies you’ll hear drifting from his shop and studio! Will it be Jingle Bells
ringing through the air? Maybe the cozy charm of Have
Yourself a Merry Little Christmas, or the lively strum of Rockin’ Around the Christmas Tree? Whatever notes float down Main Street, they’re sure to wrap you in that warm, nostalgic holiday glow.
Together, these three open houses create a holiday kickoff you won’t want to miss.
π
Let Your Christmas Stroll Continue
Find your way to the cheerful corner where
Judd’s Suds and
Simplicity on Main sit side by side, a little crossroads of suds, style, and seasonal sparkle. Their festive windows are full of whimsy and welcome — a perfect next stop as you explore downtown.
From there, let your feet carry you into one of Penn Yan’s beloved antique shops, where the past comes alive in the most magical way. Vintage ornaments, classic sleds, holiday china, old books, and well-loved treasures sit waiting to be rediscovered. Every aisle feels like stepping through time.
Follow the scent of evergreen to
The Flower Cart and Gift Shoppe and
Plants on Main, where Christmas blooms in winter whites, rich reds, holly sprigs, wreaths, pine boughs, and arrangements that look like they were gathered straight from a storybook forest. These shops bring nature’s holiday beauty to life — perfect for decorating, gifting, or simply savoring the season.
Pop into one of the local art shops or galleries, where Penn Yan’s creativity shines in paintings, pottery, photography, jewelry, and handmade pieces crafted by talented local makers. Each work of art tells a story rooted right here in the Finger Lakes.
β€οΈ Give Back While You Shop
ο»Ώ
A little holiday magic goes even further when you choose to support places that uplift our community.
A stop at
Sweet Farm Provisions or
Milly’s Pantry lets your shopping dollars stretch with heart and purpose — supporting local families, kids, programs, and the kind of community-centered work that makes Penn Yan shine year-round.
π
Help Santa Fill Those Stockings
And what’s a Christmas weekend without a visit inspired by the Man in Red himself?
Santa highly recommends swinging by
Keuka Candy Emporium, where jars of colorful confections, nostalgic treats, and chocolates wrapped like tiny gifts fill the shelves. It’s the perfect place to find stocking stuffers that make Christmas morning sparkle.
While you’re there, Santa suggests picking up an extra treat or two to leave out for him and his hardworking elves — a sweet gesture that keeps the Christmas magic alive.
β
Take a Break & Savor the Season
When you’re ready to rest your feet, downtown offers plenty of places to grab a cozy bite — whether you’re craving something quick or hoping to sit and savor a warm meal as the holiday bustle dances outside the window.
π
A Weekend Rooted in Tradition, Community & Christmas Cheer
This is the perfect weekend to begin your holiday shopping, support the local businesses that keep our village thriving, and immerse yourself in the charm of Penn Yan’s beloved Main Street.
Bundle up, bring a friend, follow the sparkle —
and let Penn Yan wrap you in Christmas warmth, one magical stop at a time.
Stay Rooted. Stay Keuka.
It truly is the most wonderful time of the year!
