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Rambles with Rachel

September 22, 2023

The Best Things to Do in Naples, NY

“Did nobody ever tell you grapes are better in September?“

-James Marriott

Are you looking for the best things to do in Naples, NY? You’re in for a treat…and not just the grape pies for which the town is known.

Naples is a quaint little town in New York’s Finger Lakes region. It’s a beautiful area full of wineries, rolling hills, and long stretches of lakeshore. My partner is from the Finger Lakes, and it’s a place I’ve grown rather fond of visiting over the past few years. Naples is located near the southern end of Canandaigua Lake.

For being a small town, there are lots of things to do in Naples, NY, especially if you like spending time outdoors. Whether you are passing through or making it your base camp, Naples is a great place to spend a day or two as you explore the Finger Lakes.

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Rachel leans against a wooden post, standing at the edge of a vineyard with green, leafy grape vines, in Naples, NY.

Getting There

The closest transportation hubs near Naples are the cities of Rochester and Syracuse, NY. From there, the drive to Naples is about an hour or an hour and a half, respectively.

  • By plane: Fly into Frederick Douglass Greater Rochester International Airport or Syracuse Hancock International Airport.
  • By train: There are Amtrak train stations in both Rochester (Louise M. Slaughter Rochester Station) and Syracuse (Regional Transportation Center).
  • By bus: Both Rochester and Syracuse have Greyhound Bus terminals.

Getting Around

The best way to get around Naples, NY is by car. It is a pretty rural area, so having a car makes it easier to reach things like trailheads and wineries.

However, once you are in Naples, you can walk to many places within the town.

Where to Stay in Naples, NY

  • During my first visit to Naples I stayed at the Maxfield Inn, a lovingly restored historic mansion.
  • The Naples Hotel has been recently renovated and offers an on-site restaurant and bar with outdoor seating.
An alley in downtown Naples, NY is strung with lights over tables and chairs set for outdoor dining.

Things to Do in Naples, NY

Take a Hike

One of the best things to do in Naples, NY, is go for a hike. Trails around Naples vary from easy to difficult. Its location in a valley offers fun hikes that include views and waterfalls! My two favorite hikes are:

Grimes Glen

Rachel stands looking at a softly cascading waterfall on a hike to Grimes Glen, one of the best things to do in Naples, NY.

The 1.1 mile hike through Grimes Glen is easy enough- as long as you’re wearing waterproof shoes. You’ll be walking along the stream bed, and some of the stepping stones will be a few inches underwater (depending on the season).

It’s worth it, though! The Grimes Glen hike features three cascading waterfalls. The third waterfall is a bit tricky to get to and requires some strenuous rope climbing.

If you enjoy waterfall hikes, check out these other trails to waterfalls in the Finger Lakes.

Conklin Gully

A valley covered in trees, looking out over Conklin Gully in Naples, NY on a summer day.

Another area that’s great for hiking in Naples, NY, is Conklin Gully. The trailhead is located just five minutes from downtown, but you’ll feel like you’re in the middle of nowhere (in a good way).

There are several trails to take around Conklin Gully. Most of them start with a steep climb but reward you with awesome views of the gorge. I enjoyed this 2.1-mile loop from All Trails, which is rated as “moderate” and took about an hour to complete.

Eat at a Local Cafe

Naples knows how to start the day off right! Most of the best places to eat in Naples, NY serve excellent breakfasts, brunches, and lunches. There are several cute cafes in town, and the food at each of them is so good.

A wooden sign for Old School Cafe, with its red school building in the background.
A table and several chairs sit outside Caruso's Cafe in downtown Naples, NY.
Old School Cafe

One of my favorite things to do in Naples is eat at Old School Cafe. They have everything from fresh pastries to chicken and waffles. With delicious coffee and a friendly staff, Old School is a great place to fuel up for the day’s adventures.

The building actually was a primary schoolhouse in the 1800s. You can either sit inside, where the decor includes things like the periodic table of elements, or outside at picnic tables. You might even get to enjoy live music!

Caruso’s Cafe

For a retro feeling (not quite as old school as Old School), step into Caruso’s Cafe on Main Street. This neighborhood spot is popular amongst tourists and locals alike. Enjoy a bagel sandwich or a smoothie as you sit in a colorful, friendly atmosphere.

Wander Downtown

A simple, but pleasant, thing to do in Naples is just to walk along the stretch of downtown. There are shops, cafes, bars, and restaurants to explore. It’s about a mile to walk from end to end of the main drag.

Celebrate Grapes

A large sign in the shape of a bunch of grapes advertises grape pies at an establishment in Naples, NY.

One of the most popular things to do in Naples is to attend the Naples Grape Festival. This annual festival occurs each September and, as the name suggests, celebrates grapes!

The Finger Lakes area is known for its fertile land that is perfect for vineyards. At the Naples Grape Festival, you can enjoy tasting wines and beverages from the region, along with live music.

The main event of the Naples Grape Festival is the Grape Pie Contest. This delicious baked good is specific to the Finger Lakes area and uses purple grapes. Similar to blueberry pie, a grape pie is both sweet and tart.

Even if you can’t make the festival, when you go to Naples, you should try a grape pie. You can purchase them from Cindy’s Pies or Monica’s Pies in town.

Visit a Local Winery

Flowers and an "open" flag outside the entrance to Hazlitt's Red Cat Cellars, one of the local wineries in Naples, NY.

If you prefer your grapes crushed, rather than baked, you should visit a local winery. Finger Lakes grapes are commonly used to make Riesling, Chardonnay, and Pinot Noir.

One of the most convenient wineries in Naples, NY is Hazlitt Red Cat Cellars, since they’re right in town! Enjoy a flight of wine samplings with a bowl of fresh popcorn in a chalet-inspired building.

The Hazlitt family (now in its seventh generation of wine-makers) has been growing grapes since 1852. They make red, white, and rosé wines right in Naples. They’re probably most known for their Red Cat Wines, which you can purchase throughout New York State.

Hazlitt also makes one of my favorite ciders, Cider Tree!

Other nearby wineries in Naples include Inspire Moore Winery and Arbor Hill Winery.

Try Some Craft Brews

Of course, you don’t only have to drink wine if you visit Naples. There are several local breweries as well!

Naples Brewing Company

Naples Brewing Company is located right on Main Street and offers small batch craft beers with local ingredients. Try the Grape Pie Sour in honor of the town’s specialty!

Engine 14 Brewing

Located on the Hazlitt property is Engine 14, named for the its fire house theme. (Founder Greg opened up the brewery after retiring from the Rochester Fire Department in 2019.) Try the oatmeal stout or the apricot wheat ale!

See a Show at Bristol Valley Theater

An old, brick building that was once a church is now a local theater in Naples, NY.

I’d be remiss if I didn’t mention Bristol Valley Theater as one of the best things to do in Naples! The theater was what first brought my partner and me to Naples, since he was performing in a play there.

Bristol Valley Theater is Ontario County’s only professional theater! Each summer they produce plays, musicals, and new works of theater. Actors come from all over the country to perform in Naples, bringing all kinds of talent with them.

(The theater itself was previously a church, and the theater seats are still cushioned pews.)

The staff at Bristol Valley Theater is warm and welcoming. Once you see a show there, you’ll want to return!

Shop Farmers’ Markets

Sunflowers grow in front of an open air market in Naples, NY.
Bunches of fresh peaches for sale on a farmer's market stand in Naples, NY.

With so many farms around, it’s no wonder that Naples, NY has some fantastic open-air markets that offer fresh produce and homemade goods. (Seriously, I could eat my weight in breads, pastries, and fruit jams.)

In Naples you can find Joseph’s Wayside Market, which sells everything from flowers to fresh berries. They also have a local wine section, of course!

By purchasing goods from these kinds of markets, you’ll be supporting local farmers, bakers, and artisans.

Honorable Mentions

If you have several days in Naples, there are more fun things to explore in the area.

  • Canandaigua Lake: Have a lake day! There are beaches and boat rental spots along the lake if you want to get out on the water.
  • Hollerhorn Distilling: If neither wine nor beer is your thing, you’re in luck! You could try a local distillery, instead. Hollerhorn Distilling makes unique spirits using maple syrup, in addition to gin, whiskey, and a fruit brandy.

I hope you are able to enjoy the adorable town of Naples, NY! Naples has all of the best things that come to mind when one thinks of the Finger Lakes: wine and waterfalls. I look forward to visiting every summer; maybe one day you will, too.

Planning a trip to the Finger Lakes? Save this post for later!

Posted In: New York State, Things to Do · Tagged: Day Trips, Finger Lakes, Upstate NY

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Comments

  1. Artizanns says

    September 29, 2023 at 2:36 pm

    You should have stopped in at Artizanns, We support over 200 artists from the Finger Lakes. Everything is one-of-a-kind unless it is a book, food or prints. Next time. We welcome everyone.

    Reply
  2. John Curtiss says

    February 19, 2024 at 5:08 pm

    A nice place to stay is Cedar Ridge Lodge just outside of Naples New York. Look it up on line Cedar Ridge Lodge the Quiet Place. Close to lakes, ski lodges and parks.

    Reply
  3. Keith McCord says

    August 13, 2025 at 2:53 pm

    The other local winery, Inspire Moore, is a wonderful family-owned business. I have been visiting them since they opened, and even joined their wine club, despite being from Long Island and only being able to visit once a year.

    Reply

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Hi there! I'm Rachel, lover of stories, history, and the great outdoors, with a penchant for the fantastical. Raised in the Adirondack Mountains of New York State and grown in New York City, I love sharing the best of both my worlds, while exploring new horizons. Come ramble with me!

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