Things to Do in Naples, New York
Need a peaceful Finger Lakes escape filled with wine, waterfalls, and pie? Head to Naples, NY! Nestled in the hills at the southern end of Canandaigua Lake, Naples is known for its vineyards, purple grapes, artsy flair, and natural beauty. When I went to college for four years in Upstate NY, I couldn't get enough of the nature and other attractions in Naples. One of the best places to visit in October for fall foliage weekends when I moved to NYC was Naples.
Whether you’re sipping local vintages, hiking scenic gorges, or tasting world-famous grape pie, this small town packs big Finger Lakes charm. I think that Naples is one of the absolute best day trips in Upstate NY. I love it and I think you will too.
Naples, NY Highlights (if you only have one day):
- Visit Grimes Glen Park: I always feel like I’ve stepped into a secret world when I hike here. You’ll walk along a gentle creek, and if you don’t mind getting your feet wet, you can wade to two gorgeous waterfalls tucked away in the gorge. You’ll thank me later—this one’s magical.
- Explore the scenic Naples Valley: I usually drive with the windows down through these hills, but hiking or biking gives you a closer look. You’ll wind past farms, forests, and views that will stop you in your tracks. I’ve been all over—and this valley is still one of my favorite hidden gems.
- Even if you are like me and don't drink much, stop at one of the local wineries to soak up the local history. I love how wineries in Naples preserve the past.
Best Time to Visit Naples, NY
If you ask me, late summer through fall (August to October) is when Naples shines. I love how the air smells like grapes and woodsmoke, and the hills look like a painter’s palette. You’ll hit peak grape harvest and fall color. But if you visit in spring or early summer? You’ll still find blooming trails and perfect weather for being outside. I’ve been in all seasons, and there’s no bad time—just different flavors of wonderful.
How to Get to Naples, NY
- If you are traveling by car: I usually come in along NY Route 21—it’s a peaceful drive, especially if you’re heading down from Canandaigua (just 45 minutes away). If you're coming from Rochester or Syracuse, plan on about 1.5 hours. You'll enjoy the scenery either way.
- By Air: I fly into Greater Rochester International Airport (ROC) when I’m not driving. Then I rent a car and enjoy the slow roll through Finger Lakes country. You’ll feel your stress melt away about 20 minutes into the drive.
- By Bus: There’s no direct line into Naples, but you can take buses to Canandaigua or Geneva and then grab a rideshare or taxi. It takes a little extra planning, but you’ll get there—and it’s worth it.
Where to Stay in Naples, NY
- Naples Hotel – I’ve stayed here for the history and charm alone. You’ll find updated rooms, a great restaurant downstairs, and the feeling that you’re part of the town’s story. It's right downtown, so you can walk to almost everything.
Best Things to Do in Naples, NY
1. Grimes Glen
Just when I thought the Finger Lakes couldn’t get any more enchanting, I wandered into Grimes Glen, and it quickly became one of the most magical highlights of the trip!
The trail began as a gentle walk along a bubbling creek, but before long I was stepping right into the stream itself, following the water upstream as it wound its way between mossy cliffs and over smooth stones.
When I finally reached the 60-foot tall waterfalls (framed by 200-foot high shale bluffs), it felt like stumbling upon a hidden world. The sheer wild beauty of the gorge is why I think Grimes Glen is one of the best things to do in Naples. It was equal parts exhilarating and serene, a natural wonder tucked quietly away in the heart of Naples.
My highlight was seeing Naples Devonian Tree, the oldest fossilized tree in New York discovered in 1882. While there are several glens in the area, Grimes Glen is the easier to access.
2. Cumming Nature Center
Next I set out along the trails at Cumming Nature Center, and it quickly became one of the most tranquil parts of my trip.
The paths meandered through tall stands of pine, across open fields, and over wooden walkways that skimmed the edge of quiet wetlands. Each section felt like its own little world: shaded forest corridors, sunlit clearings, and marshes alive with the hum of insects.
I found out that the 900-acre Cumming Nature Center is owned and operated by the Rochester Museum & Science Center. It offers a range of educational programs, learning opportunities and features over six miles of trails.
The highlight for me here was the Beaver Trail which leads to an observation tower that overlooks a 35-acre beaver pond. The Helen Gordon Trail is also worth exploring because it includes an outdoor art gallery featuring local birds and other animals.
The Haudenosaunee Trail showcases paintings by artist Ernest Smith, who is known for his presentations of the culture and tradition of the Haudenosaunee. The Pioneer Trail passes by a historic 18th-century homestead and offers interpretive signs about the lives of early settlers. The Conservation Trail features signs about the forest conservation and management practices of the Center.
I think that Cumming Nature Center is one of the best things to do in Naples, NY. Why? I love that all trails are used for skiing and snowshoeing in the winter, making this a four season getaway.
3. Ontario County Park at Gannett Hill
For me, the Ontario County Park at Gannett Hill overlook completely stole the show which makes sense since its one of the highest points in Ontario County.
If you want the best views on your trip to Naples, this is where to go. The park includes dense forests, open lands, playgrounds, tent sites, RV pads, cabins, basketball court, soccer and Frisbee fields, pavilions and picnic sites with benches, tables and grills. There are 13 miles of hiking and biking trails, including a portion of the Finger Lakes Trail system. There is also a popular fishing pond.
It was one of those places that reminded me how vast and beautiful this region really is, a hilltop escape where time seemed to slow down with every breath of fresh mountain air, definitely my highlight.
4. Parish Glen - Conklin Gully
While not as well known as Grimes Glen probably because it has less water, Parish Glen - Conklin Gully was nevertheless a fantastic stop. Parish Glen - Conklin Gully is part of the High Tor Wildlife Management area and requires a bit of climbing but it is worth it for the views it affords.
The entrance to the gully is located on Parish Hill Road, and the main "trail" is actually the creek bed so be prepared to get your feet wet, unless you are visiting during summer months when the creek is dry. There is a nice waterfall but to see it requires some rope climbing. There are also a few smaller falls.
My favorites were the twisting waterfalls of Conklin Gully, each one hidden like a secret, with sculpted rock walls rising up around them. They felt like natural cathedrals carved by time, and walking through them was like wandering into another world.
5. Bristol Valley Theater
If you want less outdoorsy type things to do in Naples, there are some good options, like seeing a play, wine tasting, visiting a maple farm and much more.
First things first...one of the things I loved most about Bristol Valley Theater was how it felt like the creative heart of Naples—an intimate space where the arts came alive right in the middle of the Finger Lakes.
My favorites were the summer productions, where professional actors from New York City shared the spotlight with local talent. There was something magical about seeing Broadway-caliber performances tucked into this small town—it made every show feel like a hidden gem you’d stumbled across.
6. Inspire Moore Winery & Vineyard
One of the things I loved most about Inspire Moore Winery & Vineyard is its history. Inspire Moore Winery & Vineyard is located in what was once the area the Seneca Indians called Nundawao, where Naples was later founded. The building that houses the winery was at different times a tavern, a stagecoach stop and a carriage house. You'll be taking a walk through history here, that's why it was such a highlight for me personally. During its transformation into a winery, many original elements were used such as old timbers.
Today, Inspire Moore is a boutique winery that produces a few thousand cases of Finger Lakes appellation wines , with focus is on aromatic varietal whites, varietal reds, ice wine and small lots of blends.
My favorites were the wines named after ideals—“Love,” “Wisdom,” “Joy,” and “Peace.” It made the whole tasting feel like an invitation to celebrate life’s deeper layers.
7. Arbor Hill Grapery & Winery
Arbor Hill Grapery & Winery won me over with its little surprises that went far beyond wine. It had that rare mix of tradition and playfulness that made exploring it an experience in itself.
My favorites were the grape-inspired specialties—from their signature wines to jams, mustards, and sauces, all crafted with the vineyard’s own Concord and other heritage grapes. Tasting through them felt like discovering just how versatile the grape could be, each product telling a slightly different story.
I also loved the historic setting, with the rustic old buildings and the cozy tasting room that seemed to whisper of past generations. It felt less like a commercial winery and more like being welcomed into a living tradition of winemaking in the Finger Lakes.
8. Hunt Hollow Ski and Snowboarding Resort
Returning to outdoor activities which this area is known for, Hunt Hollow is a private ski and snowboarding resort near Naples, New York. One of the things I loved most about Hunt Hollow was how it felt like a hidden world tucked into the hills. Unlike the sprawling commercial resorts, this private ski club had an intimacy that made every run feel like it belonged just to you.
My absolute favorite thing was the view from the top on a clear day.
9. Wesley Hill Nature Preserve
One of the things I loved most about Wesley Hill Nature Preserve was how it felt like stepping into a living painting—towering old-growth trees, winding trails, and sudden overlooks that opened into wide, breathtaking views of the hills and valleys below. It was both wild and welcoming, the kind of place where you could lose yourself and find yourself at the same time.
My favorites were the massive hemlocks and hardwoods that stood like sentinels along the paths. Some were centuries old, their roots knotted deep into the earth, and walking among them felt like entering a cathedral of green.
But my absolute favorite thing at Wesley Hill Nature Preserve was reaching the scenic overlooks, where the world seemed to drop away into the rolling Bristol Hills.
Standing there, the wind in your face, the silence broken only by birdsong or rustling leaves, you couldn’t help but feel the immensity of the landscape—and your small, grateful place within it.
10. Brew And Brats At Arbor Hill
One of the things I loved most about Brew And Brats At Arbor Hill was how it combined the easygoing feel of a neighborhood gathering spot with the richness of Finger Lakes flavor. It was a place to linger, laugh, and feel like you were part of something local and genuine.
My favorites were the signature sausages, made with Arbor Hill’s own recipes. Each brat had its own personality—smoky, spicy, or infused with wine—and paired perfectly with their craft brews. It turned a simple meal into an experience where you could taste the creativity that went into every bite.
11. Hollerhorn Distilling
Hollerhorn Distilling was equal parts gathering place, concert hall, and creative stage. Tucked into the hills above Naples, it carried the rustic charm of the Finger Lakes but layered it with a bold, artistic energy.
12. Wohlschlegel’s Naples Maple Farm
My favorites were the maple tastings at Wohlschlegel’s Naples Maple Farm. Light amber, rich dark, and even infused varieties each told their own story of the trees and the season. Tasting them side by side made me appreciate just how much craft and patience lives in every drop.
I also loved the farm tours, wandering through the sugarbush and hearing the gentle history of how this tradition has been passed down. The woods themselves felt alive with it, as if the trees were quietly proud of what they gave.
But my absolute favorite thing was the unexpected maple creations, from maple cream and candies to barbecue sauces and glazes.
13. Hazlitt Red Cat Cellars
One of the things I loved most about Hazlitt Red Cat Cellars was how it managed to be both historic and playful at the same time. Set on the grounds of a former monastery, the place carried an air of heritage and craftsmanship—but with a wink and a smile that made it anything but stuffy.
Conclusion
Here you have it, these are the best things to do I discovered in Naples so far. Naples, New York is a place where nature, art, food, and community come together in the most authentic way. From waterfalls and trails to wineries, theaters, and farms, every experience feels welcoming and genuine, a small town with a big heart that leaves a lasting impression.
Booking Checklist
1. Book Your Flight - I use Expedia because I like their mobile app with my itinerary. They've helped me re-book flights on many occasions. Once you reach their Gold tier, support is especially good.
2. Book Your Hotel - I use Booking.com or Expedia, depending on my destination.
3. Book Your Rental Car - I use Expedia.
4. Book your tours on Viator or Get Your Guide.
