Small Towns to Explore Near Canandaigua: Why Naples, NY Should Be on Your List

Canandaigua offers plenty to fill a Finger Lakes getaway, but part of the fun of staying in this region is discovering the smaller communities just beyond the city. A short drive can lead to a completely different atmosphere, with quiet Main Streets, local shops, scenic landscapes, and attractions that give visitors a deeper look at the Finger Lakes.

One small town worth adding to your itinerary is Naples, NY. Surrounded by rolling hills and known for its outdoor beauty, arts community, and long connection to grape growing, Naples offers a slower pace that makes it ideal for a relaxed day trip.

Discover the Character of Naples

Naples sits in the southwestern portion of Ontario County and has the kind of personality that makes small-town exploring so rewarding. The community is surrounded by hills, forests, streams, and scenic countryside, yet the village itself offers restaurants, shops, local art, and plenty of places worth stopping.

Instead of arriving with a packed schedule, Naples is a place where it pays to leave some room to wander. Spend time exploring Main Street, stop somewhere that catches your eye, or simply enjoy the drive through the countryside.

For guests staying near Canandaigua, a visit to Naples also adds another perspective to a Finger Lakes trip. It is close enough for an easy outing yet feels distinctly different from the lakefront and downtown experiences farther north.

Take a Walk Through Downtown Naples

Downtown Naples is small enough to explore at a comfortable pace. Local shops and businesses give the village its character, and visitors looking for locally made items can find work from Finger Lakes artists and craftspeople.

One stop is Artizanns, a gallery in a historic home on Main Street showcasing handcrafted work by regional artists. Browsing shops like this is a great way to find something that feels connected to the area rather than a typical souvenir.

A downtown visit can easily be paired with lunch or a sweet treat before continuing on to one of the area’s outdoor attractions.

Explore Grimes Glen

Nature lovers should make time for Grimes Glen Park, located just minutes from downtown Naples. The glen is known for its deep gorge, creek, wooded surroundings, and two impressive waterfalls.

Part of the fun is that visiting Grimes Glen feels like discovering a hidden piece of the Finger Lakes. The trail begins with an easier section, while reaching farther into the glen can involve walking through water and navigating wet or uneven surfaces. Visitors planning to explore beyond the first section should come prepared with sturdy footwear and check current trail conditions before heading out.

It is a beautiful option for travelers who want to mix small-town sightseeing with a little outdoor adventure.

Taste Naples’ Grape-Growing Heritage

Naples and grapes have been connected for generations. Commercial grape growing took hold in the Naples Valley more than 150 years ago, and that history remains an important part of the community today.

Local wineries give visitors an opportunity to experience that tradition firsthand, but there is another Naples specialty that should not be overlooked: grape pie. The sweet, distinctly local dessert has become closely associated with the town and is worth trying when it is available.

Naples celebrates its grape heritage in an especially big way each fall with the annual Naples Grape Festival, but you do not have to visit during festival weekend to appreciate the influence grapes have had on the area’s food, farms, wineries, and identity.

Enjoy the Scenery Along the Way

The trip to Naples is part of the experience. The surrounding Bristol Hills and Finger Lakes countryside make this an ideal area for travelers who enjoy scenic drives and a slower approach to sightseeing.

Rather than treating Naples as one attraction to check off a list, make the journey part of your day. Leave time for an overlook, a roadside stop, or an unexpected detour. That sense of discovery is one of the best reasons to explore the small towns surrounding Canandaigua.

Make 1795 Acorn Inn Your Home Base for Exploring

A Finger Lakes getaway is about more than seeing one destination. At 1795 Acorn Inn Bed & Breakfast, our Bristol Valley location puts you within easy reach of Canandaigua, Naples, scenic drives, waterfalls, wineries, and the small towns that give this region so much character.

After a day of exploring, come back to a peaceful setting with beautifully appointed guest rooms, private baths, fireplaces, a gourmet breakfast, gardens, and an outdoor hot tub. Whether you are planning a quiet weekend or a few days of discovering more of the Finger Lakes, we would love to welcome you.

Call us at (585) 229-2834 or reserve your stay online and make 1795 Acorn Inn part of your next Finger Lakes escape.