The Grape Pie Capital of the World

Naples holds a title that no other town on the planet can claim: Grape Pie Capital of the World. This is not marketing hyperbole. The town and surrounding hillsides grow Concord and other native grape varieties in sufficient quantity that local bakers — primarily Monica’s Pies and Cindy’s Pies, both institutions — produce thousands of grape pies annually, shipping them across the country. The grape pie is made from whole grapes, sugar, and a thickener in a double crust, and the flavor is intense, sweet-tart, and entirely distinct from anything made with grape jelly or juice. If you have not had one, you have not had one — there is no substitute or approximation.

The tradition peaks each September at the Naples Grape Festival, a two-day event that draws over 60,000 visitors to a town of about 1,000 residents. The festival fills the village streets with pie vendors, grape stomping, craft booths, live music, and a parade. It is the single largest food festival in the Finger Lakes and has been running since 1961.

Bristol Mountain

Bristol Mountain sits on the hills east of Naples and is the premier downhill ski area in the Finger Lakes region. The mountain has a vertical drop of 1,200 feet — the highest between the Adirondacks and the Rockies along this latitude — served by 38 trails across 138 acres of skiable terrain. Two quad chairlifts and a surface lift move skiers up the mountain. The base lodge offers equipment rentals, lessons, and a cafeteria. Night skiing runs on select evenings through the season, typically December through late March.

In summer, Bristol Mountain operates as an aerial adventure park and also hosts the Bristol Mountain Aerial Adventures course — ziplines, rope bridges, and climbing elements through the forest canopy. Bristol Mountain Music in the Mountains summer concert series has featured national touring acts in the past, though schedules vary by year.

Grimes Glen

Grimes Glen is a box canyon on the southern edge of the village that contains two waterfalls, each approximately 60 feet tall, in a narrow gorge cut through Devonian-era shale and sandstone. The hike to the falls is short — about three-quarters of a mile each way — but it requires walking directly in the creek bed for much of the route. There is no dry path. Waterproof footwear is essential (old sneakers at minimum; water shoes or waterproof hiking boots are better). The creek is usually ankle- to calf-deep in summer, with some deeper pools to navigate.

The reward justifies the wet feet. The first waterfall drops into a wide pool surrounded by towering rock walls. The second, a short scramble beyond, is even more enclosed. Grimes Glen is also significant to paleontologists — fossil trees from one of the Earth’s oldest forests (approximately 370 million years old) were discovered here, making this one of the most important paleobotanical sites in the world. The gorge is open and free to access from the trailhead on Vine Street, though there are no facilities or rangers on-site.

The Village

Naples’ village center is a single main street — Route 21 — with a small commercial district. The Redwood Restaurant is a year-round local gathering place serving American comfort food. Bob & Ruth’s Vineyard Restaurant offers casual dining with a menu that leans into the grape harvest theme. The Brew & Brats at Arbor Hill operates at a winery complex north of the village where you can sample wines and grape-based specialty products, including grape mustard and wine jellies.

The village sits at the very southern tip of Canandaigua Lake, where the steep hillsides close in on both sides. The drive into Naples from the north on Route 21 — descending into the valley with the lake narrowing behind you and the Bristol hills rising ahead — is one of the more scenic approaches to any Finger Lakes town, particularly during fall foliage in late September and early October.

What to Do

• Grape pie pilgrimage: Monica’s Pies (on Route 21 north of the village) and Cindy’s Pies (on Main Street) are the two essential stops. Both ship nationwide, but buying a pie warm and eating it in the car is the proper first experience.
• Grimes Glen: Free. Trailhead on Vine Street. Allow one to two hours round trip. Wear waterproof shoes. Best visited June through September when water levels are lower.
• Bristol Mountain: Skiing December through March. Summer activities June through September. Check the website for current rates and hours.
• Hi Tor Wildlife Management Area: A 6,100-acre preserve on the hills west of Naples with trails for hiking and cross-country skiing. The overlooks offer panoramic views of the Canandaigua Lake valley.
• Fall foliage drive: The Bristol hills around Naples consistently produce some of the best fall color in western New York. Peak is typically the first two weeks of October. Drive any road south or west of the village for maximum effect.

Practical Details

Naples is located on Route 21 at the southern end of Canandaigua Lake, approximately 30 miles south of Canandaigua and 50 miles south of Rochester. Parking is free in the village. Lodging is limited in Naples itself — most visitors stay in Canandaigua or the surrounding area, though several vacation rentals and bed-and-breakfasts operate nearby. During the Grape Festival (late September), plan for traffic and park in the designated lots — the village streets close to vehicles.

Locals Know

The best grape pie is a matter of fierce local debate — Monica’s partisans and Cindy’s loyalists do not easily cross lines. The real answer is to buy one of each and conduct your own tasting. Also: Grimes Glen is at its most dramatic in spring (April-May) when the water volume is highest and both falls are thundering, but the creek is also deeper and colder. Summer is the easier, more comfortable visit. And for fall color, locals skip the main roads and drive Italy Hill Road south of Naples — the views across the vineyard-covered slopes are the best-kept visual secret in the western Finger Lakes.