Jeromes U-Pick Grapes cover

Explore Naples

Nestled in the hills at the southern end of Canandaigua Lake and one hour south of Rochester, Naples is known for its beautiful natural surroundings, which have inspired many artists and farmers to create and work here. With its strong connection to the grape industry, Naples is home to several wineries and grape-themed events, such as the celebrated Naples Grape Festival.

The drive between Rochester and Naples is breathtaking during fall. To add scenic variety to your trip, consider taking a different route down and back along County Roads 33, 34, 64, 12, or 21.

Best of Rochester - Day Trips Around Rochester book

Day Trips Around Rochester, New York

Best of Rochester Award-Winning Book for Best Published Literary Work of 2023.

Plan Your Day Trip to Naples

Bob and Ruths Vineyard
Bob and Ruth’s
Carusos Cafe
Caruso’s Cafe
Old School Cafe
Old School Cafe


Enjoy a delicious meal at Bob’s & Ruth’s Vineyard Restaurant or the Old School Cafe, a restored 1870 schoolhouse. Stop into Caruso’s Cafe for a breakfast sandwich and a tasty beverage.

Grimes Glen second fall
Grimes Glen second waterfall cave
Grimes Glen first waterfall
Grimes Glen


Grimes Glen is open to the public and free to enjoy. To reach the two 60-foot waterfalls, you will need to walk through the creek. If you visit the glen during a weekday or early in the day, you may have the area to yourself. However, as the day goes on, especially on busy days like holidays or hot August afternoons, the parking lot can fill up, and you may need to park in a public lot on Main Street and walk to the glen.

Small Family Restaurants Roots Cafe Naples
Roots Cafe
Redwood Restaurant
Luigis Diner
Luigis Diner


Try Luigi’s or Naples Wood-Fired Pizza & Smokehouse BBQ for a quick break. Or indulge in comfort food at Redwood Restaurant or a farm-to-table meal at Roots Cafe.

Olde Country Store and More North Cohocton
The Olde Country Store and More – 1849
Hazlitt Red Cat Cellars
Naples Brewing Company
Naples Brewing
Josephs Wayside Market
Joseph’s Wayside Market


After lunch, stop into Artizanns to browse handmade crafts, music, and locally produced food from over 200 Finger Lakes artisans.

Drive 10 minutes south on New York State Route 21 to The Olde Country Store and More – 1849 in North Cohocton. The store is known for its vast selection of old-fashioned candies, local and German products, and the largest variety of 1000 Islands River Rat Cheese in the area. You’ll also find Green Heart of the Finger Lakes merchandise designed by the store’s proprietor.

On returning to Naples, stop at Lynnie Lou’s Homemade Ice Cream—look for their harvest-inspired grape custard in September. Then, head to Joseph’s Wayside Market to browse their selection of local and regional products, including grape pie. You can also purchase a variety of local grapes or pick your own at Jerome’s, just a few minutes south on New York State Route 53.

Experience local wine, beer, and spirits from Hazlitt Red Cat Cellars, Inspire Moore Winery, Arbor Hill Winery, Naples Brewing Company, Hollerhorn Distilling, and Engine 14 Brewery.

Alternatively, go for a hike at Cumming Nature Center, where you’ll find marked trails, including one that passes through a beautiful stand of tall red pines.

If you head out of Naples before dinner, consider stopping into the Cheshire Union south of Canandaigua on New York State Route 21 to explore more local art. Located in an old four-room schoolhouse, it serves as a gift shop, artist studio space, gallery, and classroom for over 120 local artists and vendors. Check out The Company Store on the first floor for dinner on the go.

The Social at The Naples Hotel
Naples Hotel


Enjoy a fine meal at The Social Restaurant & Taproom in the haunted 1895 Naples Hotel. Or dine on the shore of Canandaigua Lake at the seasonal Sawmill Restaurant.

Ontario County Park Gannett Hill Jump Off Trail viewing platform
Jump Off Trail viewing platform in Ontario County Park on Gannett Hill


Look at Bristol Valley Theater’s upcoming shows so your day trip coincides with one of their outstanding live performances. Alternatively, you can watch the sunset from The Jump Off on Gannett Hill, where you may glimpse the Rochester city skyline in the distance.

Signature Events

Bristol Mountain
Autumn lift rides at Bristol Mountain

Bristol Mountain Fall Sky Rides


Enjoy a 20-minute round-trip ride on the Comet Express chairlift on weekend afternoons from mid-September through October. Absorb the rich fall colors while facing Stid Hill on the ride back down. Admission fee. 5662 New York State Route 64

Jeromes Grapes multicolored

Naples Grape Festival

late September

The two-day grape festival celebrates local music, art, and food. The wine-tasting tent is a popular destination featuring the finest regional wines, craft brewers, and distilleries. The World’s Greatest Grape Pie Contest is a must-see event. Unique to the Finger Lakes region, grape pies were created in the 1950s by Naples resident Irene Bouchard. Getting to the Naples Grape Festival can be hectic, as there is only one main thoroughfare in and out of the village. Plan to arrive before 11 a.m. to avoid heavy traffic. Parking is available at Hazlitt Red Cat Cellars, with a free shuttle bus to take attendees directly to the festival grounds at the Memorial Town Hall and Naples High School. 154 N. Main Street

Google Map of Locations

View the map separately here.

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Jeromes U-Pick Grapes cover
Cover Photo: Looking North Toward Naples from Jeromes U-Pick Grapes

Where are your favorite places to visit in Naples?

Your insights and experiences are valuable. Please share them in the comments.

Debi Bower, Day Trips Around Rochester NY

Debi Bower is the founder and creative director of and author of the award-winning book Day Trips Around Rochester, New York.

People often ask me if I get free access to places while exploring. The answer is no unless I’m invited to previews or granted behind-the-scenes access as part of my media role. Generally, I don’t mention my project, Day Trips Around Rochester, NY, because I want the same experience you would have. I create and share content simply because it brings me joy. I would appreciate your support—a cup of coffee or two to help fuel future field trips—if you have found valuable information here that has helped you explore the Rochester area.

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