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Discover the Magic of the Holiday Season in Naples, NY!

  • Writer: Naples Grapes
    Naples Grapes
  • Nov 20, 2025
  • 3 min read

Updated: Dec 7, 2025


As the holiday season settles over the Finger Lakes, there’s something especially magical about Naples this time of year. Our little town comes alive with twinkling lights, the smell of good food, and the buzz of community. Plus, we have an incredible lineup of local events that make December feel truly special!


Embrace the Joy of Local Shopping


Whether you’re a long-time resident or planning a day trip, Naples offers countless reasons to slow down, wander, and soak in the joy of the season. One of the best parts of the holidays is gift-giving! When you shop locally, those gifts come with something extra: heart. Local shopping doesn’t just give your presents a unique flair; it supports the artisans, makers, business owners, and families who pour themselves into their work all year long. Every purchase truly matters, and in a place like Naples, you can feel that impact!


Exciting Holiday Events Await!


Kicking off the festivities is Lauren Hirsh’s 9th Annual Holiday Pop-Up at the Golf Course. Beginning November 29th, this beloved market is open every Saturday & Sunday from 10 AM–5 PM right up until Christmas. It’s one of those stops you don’t want to rush through! You’ll find 40+ artists and vendors who create handcrafted gifts and seasonal favorites.


But Naples doesn’t stop there! Just across from Bob and Ruth’s, another incredible Holiday Pop-Up Sale brings more festive energy to town. This gathering of local vendors is truly a hidden gem! It offers a wide variety of antiques, handcrafted goods, upcycled clothing, maple syrup, toys and games, unique decor, jewelry, pottery, and so many other things that you won’t find anywhere else. With multiple dates and flexible hours, it’s easy to swing by no matter what your schedule looks like:


  • November 29th & 30th: 10 AM–4 PM

  • December 4th & 5th: 3 PM–7 PM

  • December 6th & 7th: 10 AM–4 PM


And we cannot forget about the event at Barh’s Den, located at 6068 State Rt 53 in Prattsburgh. Their holiday sale has plenty of wood ornaments, wreaths, spices, blends, paintings, and more! Here are the dates:


  • December 5th & 6th: 10 AM–5 PM

  • December 7th: 2 PM–5 PM


Light Up Naples: A Spectacular Celebration


Of course, one of the most anticipated events of the season is Light Up Naples on December 13th from 5 PM–8 PM. Main Street transforms into a glowing celebration, lined with shops, vendors, music, treats, and festive energy everywhere you look! It’s the kind of event that reminds you why small towns feel so special during the holidays. Neighbors greet neighbors, kids laugh, and families bundle up and stroll together under a blanket of lights.


Explore Year-Round Favorites


And that’s just scratching the surface of what Naples has to offer! Make sure to explore our year-round favorites too: Naples Herbs and Art, Artisans, Back to the Earth Rock Shop, FLXMusic, and countless other hidden gems tucked throughout town. Each one brings something unique to the community—art, herbs, beauty, craft, talent, and passion!


Indulge in Local Flavors


While you’re out adventuring, you’ll definitely want to treat yourself to some local flavors. Naples is home to an incredible lineup of restaurants and cafés, including Caruso’s, Hollerhorn, Redwood, Roots Café, Old School Café, The Naples Hotel, and many more! Whether you’re craving a warm meal after shopping or looking to cap off the night with a drink and good company, there’s something for everyone.


A Season to Connect and Celebrate


In a season that often feels rushed, Naples offers the chance to slow down and enjoy moments that matter: connection, creativity, tradition, and community pride. I genuinely encourage you to make the trip, whether you’re coming from across town or across the region. Your support helps our artists and small businesses not just survive, but thrive! And in return, they help create the holiday magic that makes this town unforgettable.


If you’re visiting from out of town, Naples makes the perfect weekend getaway! I personally recommend the Seasons of Life Airbnb. It’s comfortable, welcoming, and the perfect spot to unwind after a full day of exploring everything our town has to offer.


Either way, be sure to come experience Naples, New York this season.


Shop.

Eat.

Explore.

Celebrate!


Let the lights, the people, and the spirit of our community fill your holidays with warmth!


Here is a fun flyer with all of the awesome events in the area!!


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