[itinerary | lodging] It’s been a year since you started your newfound Lake Life. From that first breath of fresh Upstate NY air, to solving the existential mysteries of the surrounding Finger Lakes, to celebrating the open highway with your partner in crime— you’ve divided and conquered the region. But Upstate NY has too much to do, and you’ll always return home to the Lake with another case of FOMO.

Downtown Canandaigua NY

So you get back to your (relatively new) roots. Conesus Lake’s big sister to the East — Canandaigua — once again beckons for your attention. Last year at this time, you started taking the prized shot from the top of every lake, including Canandaigua’s sparkling Kershaw Park coast. Now it’s time to dive a little deeper into the cities and towns that cleansed you and raised you from the ashes of a past life.

A classic American Main Street – Canandaigua’s Historic District

Canandaigua Commons

You start in the traditional downtown of Canandaigua, at the split between North and South Main Street, and walk downhill. Canandaigua’s historic district is clean, colorful, and pedestrian friendly. Polished sidewalks and well-manicured landscaping inform you the community cares and the government puts its money where its mouth is. As you walk past a men’s fashion store, an indie toy shop, a homemade jewelry store, and an olive oil shop, the typically American Revivalist buildings open up to the Commons, a quaint city courtyard with a giant beach chair. “I must admit my confusion,” you bellow in your best Paddy Considine accent as you settle into the Canandaiguan throne. “I do not understand why petitions are being heard over settled succession!” A passerby gives you a weird look — clearly not a fan of House of the Dragon. Or American politics.

Sit and rest a spell at Canandaigua Commons

You are pleasantly surprised by the small business offerings of Canandaigua. A new American bistro’s sidewalk patio is bustling with patrons; at the bottom of the hill, a brewery’s giant aluminum kettles catch the light through the windows of an unassuming redbrick building. Even vacant storefronts entice you, beaming with the pride of a prior America still remembered by your grandparents. A solid mix of old and new. You wave your hand over the modern pedestrian alert system, and the cars politely wait for you to cross Main.

Forget it, Jake– it’s Toon Town.

Kershaw Park

Upon returning to your car, you continue down Main Street and cross US-20 toward the “tourist” section of Canandaigua — the pier and Kershaw Park. Lake Shore Drive reminds you of Ocean Drive in Miami Beach, with plenty of shoreside bars, seafood bistros, green trails, and blue water as far as you can see. Lovebirds sit hand-in-hand on one of the many swings overlooking the Lake. Ducks dive and surface with a tasty meal. Aunties surveil the street from their balcony perches. A few pontoon boats anchor near the shore of the park, the passengers dipping their toes in the water. All this is not even thirty minutes from your house.

Canandaigua Days

Depending on who you ask, either Drew Barrymore or a famous linguist once said: of all the endless combinations of words in all of history, “cellar door” is the most beautiful. What’s behind a cellar door can be scary, but it can also be immensely satisfying. You don’t know until you open it. And like Jake Gyllenhaal in Donnie Darko, the liquid force of fate propels you forward. And by liquid, you mean the kind found behind wine cellar doors.

Heron Hill Tasting Room

Thus no trip to Canandaigua would be complete without making a few stops along the Canandaigua Wine Trail. The western branch of the trail originates from the pier district south along Route 21, through incredible vistas of mountains dominating the awesome canyon formed by Canandaigua Lake. It’s late September, with fall foliage about to peak in this region of New York State. You find yourself lost in the forest as you wind your way to your next destination: the Heron Hill Tasting Room.

Heron Hill Tasting Room at Canandaigua Lake

The tasting room seems like a small building at first, but a special event with vendors, live music, and a food truck has given rise to a larger-than-usual crowd. You sneak inside and observe tall ceilings supported by solid wood frames, two large bars and a handful of high-top tables, and barrels and shelves of wine spread around the tasting room. You feel a little like Alice in Wonderland, cramming yourself through a small cellar door only to find a larger world beneath and within. Do you drink the bottle labeled “Drink me”?

You settle into a place at the bar on the left and a server greets you with the selections. Much to your liking, the wines at Heron Hill tend to skew on the dry side. You’re normally a red wine drinker, but today you enjoy the white selections a lot more than usual. An Eclipse White tastes dry and sharp, while the Reserve Grüner Veltliner feels like drinking a fine cheese. You are most definitely not a sommelier, but you learned a few tips from one years ago. You switch to reds and observe the slow tears of the Classic Blaufränkisch and the Reserve Baco Noir — evidence of either a high sugar content or a high alcohol content. Based on the buzz you’re feeling from a mere tasting, you believe it to be the latter. You top it off with a taste of “bubbly red,” which you didn’t know existed. More mysteries from the Finger Lakes? You just can’t call it champagne, of course. Ultimately you decide to buy a couple bottles of the dry white Veltliner to take home, but not before discovering the stairs down to the cellar, where presently a jazz band croons for the other oenophiles. A good place to take a break before venturing on.

It’s red champagne

Hazlitt’s Red Cat Cellars

The next winery on the list lies just beyond the southern tip of Canandaigua Lake, in the Village of Naples — close to Italy Valley, NY. And given the steep mountains, valleys, and sprawling vineyards overlooking pristine blue water, it’s no surprise the original settlers compared this area to the Italian peninsula. As the mountain flattens out into a thin valley with Route 21 as its spine, you spy a large operation hugging the base of the mountain to the north overlooking rows and rows of grapevines. The cool cat on the sign welcomes you to Hazlitt Red Cat Cellars. You know he’s cool because he’s wearing sunglasses. You approach yet another cellar door carved into the side of a Tudor-style tasting room.

Hazlitt Red Cat Cellars in Naples, NY

Hazlitt definitely has more of a Jimmy Buffett feel to it compared to your last stop, and you’re on board for it. You pony up to the tasting bar and ask the server about the selections.

“Are you more dry wine or sweet wine people?”

“Dry,” your companion says, dryly.

The server explains that the microclimate of this region influences the grapes to favor a sweeter wine, which is Hazlitt’s main M.O. She suggests a few semi-dry options, which — though sweet for your taste — go down smooth and hit all the right notes. You sit back and admire the kitschy nautical themes of the tasting room, surrounded by ship wheels and old boat hoists. People love the Lakes here, and you’ve learned to love them, too. You’re feeling more social again, like you’re part of something and not isolated from everything. You’re ready to open the cellar door not to hide away inside, but to step out into the sunshine and rain.

Fall Foliage

Naples NY Grape Festival ’23

When you wander out from Red Cat Cellars, you take in a clearer view of the Valley. Now you notice the tents and crowds and purple banners from this elevated vantage point. Even as the sunshine turns to rain, you are curious about the festival and make your way through Naples. You just stumbled upon the Annual Naples Grape Festival.

Mountain fog over Hazlitt’s

All along both sides of Main Street, tents and booths and even garages open up to a steady stream of festival-goers. Naples is teeming with life and smells and sounds. Artisans peddle their hand-crafted wares, distilleries market grape sours, even local children sell tickets to play a homemade carnival game for the chance to win a prize. Down a side street, food trucks offer Italian sausage subs with freshly grilled peppers and onions while a fried dough stand prepares sweet fluffy elephant ears and funnel cakes. The town hall’s grounds — empty the first time you passed through Naples — transform into a full-on tent village, with blues music on one corner, wine tastings on another, and a church group kitty-corner from a grape-infused cannabis gummy stand. If this isn’t a microcosm of America, you don’t know what is.

Naples Grape Festival in Naples, NY

After scoping out the scene, you settle on the most popular booths: the ones with grape goodies. You’ve heard of grape soda, but never grape ice cream. The cone is sweet, creamy, and delicious– purple and vanilla with hints of grape. You realize it will make a perfect snack while you wait for a grape pie, as the line wraps around the corner from the shop onto Main Street. When you finally approach the friendly baker, you can smell the homemade crust and feel the warmth of the oven when she hands you the box. You can hardly stop yourself from eating it right there in the street.

Grape Ice Cream / Grape Pie

As you continue along Main Street toward the Village’s south end, the festival quiets down a little. You pass by several small churches sporting beautiful façades. Not the church-going type, you still admire the architecture, sanctuary, and community provided by these buildings. A safe quiet zone no matter who you are or what you believe, each one a little different from the one before. The freedom to go wherever or to not go at all.

Stained glass, red doors

The Fish Bowl

A sudden break in the row of buildings leads you to expect another city commons, like in Canandaigua. Instead you’ve walked into the rear of a theater, so to speak. A sliver of grass in downtown Naples features wooden benches and a platform stage. In a way, it reminds you of another church– a place where time and space are defined by those who occupy them. You can’t resist climbing onto the makeshift wooden stage. Are you ready to be the star? “To be or not to be,” you ask. But nobody is clapping. Maybe this wasn’t the right platform for you. You still prefer to retain some privacy in this chronically online world.

Think about your life, Pippin

In the Bier Garten of Eden, Baby

So you get off your soap box and proceed down Main Street. Despite the rain, the sidewalks feel like walking in Manhattan as people shuffle past each other on their way to the next festival stop. Something catches your eye between two houses. “Come out back – live music & cold beer,” scrawled in chalk, and a red carpet rolled out just for you. The Bier Garten invites you once again to descend the stairs into the cellar, into the backroom, into that place you can’t see without taking a risk.

Off the beaten path in Naples

The Bier Garten reveals itself to be a cozy backyard hang-out, with a fire pit, bar stand, and small stage where a drum kit and guitars have been set out. A handful of patrons surround the fire pit or hang out off to the right of the stage, beyond the tall picket fence. Colorful metal bar stools provide ample seating for guests. You scout a wooden counter along the fence, and your companion posts up while you investigate the beer list. With nothing but a row of cans for reference, you ask the bartender — a lively and friendly man in a red shirt — for two cans that say “Hi-Neighbor!”

“Hi-Neighbor beer?” he asks, a little confused.

“Whatever this can is–” you point, and he realizes the brands are displayed inside toward him.

“Two Narragansetts comin’ right up! Five bucks apiece.”

You grab the cans and blush, a little embarrassed for not recognizing the brand. Then again, what’s a Rhode Island beer doing in a backyard beer garden in Naples, New York? It’s no matter. The beer is good, the people are friendly, and the atmosphere is, as the kids say, chef’s kiss.

Scenes from the Bier Garten, Main Street, Naples NY

“Hi neighbor!” As you prepare to head out from the festival, you are stopped by a group of four who have been eyeballing you and your companion since they came in. They read the words Conesus Lake above the House on your shirt. Your cover is blown. You’re exposed to the world.

“We want to get to know you,” says the woman with the sandy curls. “We have a great group on Conesus Lake!”

“So what’s Conesus Lake House?” the man in the Bills cap asks.

Admittedly, you are caught off guard meeting other Conesus Lake people out in the wilds of the Finger Lakes. You acknowledge your identity as the voice behind the T-shirt, the rookie lake explorer, the teller of upstate NY stories. Without giving away too much, you point them to your website. New friends and neighbors can always find you in the church you built to yourself, this WordPress stage.

Liugi’s

In the center of Naples there is, of course, a pizza shop. You’ve worked up an appetite from all the socializing, so you stop into Luigi’s for a slice. The interior seems to have remained the same since 1978– which is typically a good sign when it comes to American pizza shops. From the marquee-style menu to the combination air hockey/arcade room, Luigi’s exists as a chapter in a paperback you forgot in your desk at school long ago. You sit outside and watch the village pass by until a young boy in a mustache brings out the steamy fresh pie. The dough is thick and soft, the tomato sauce sweet, and the cheese gooey. It’s a perfect upstate pizza pie. You scarf it down and prepare to trek home.

Got a quarter?

Bristol Springs Viticulture

The road back home veers off Route 21 just outside the Village, climbing high into the mountain overlooking the great valley of the Canandaigua inlet. Eager to cut into that grape pie, you almost miss a flag waving from the mountain side of the road. “GRAPES” it says, and you realize for all the time you spent at the Grape Festival, you did not once encounter the fruit itself. You cut a sharp left up the gravel driveway to a small white barn. Behind you, rows of Concord grapevines stretch for an acre.

Bristol Springs Viticulture, Bristol Springs Road, Naples NY

You initially assume this is another honor system stand, like so many of the produce stands around the area. But then you hear a faint voice call “Hello.” “Hello?” you answer into the barn. “Hello!” the voice insists again with a chuckle, and you realize it’s coming from behind you, through the grapevines — a friendly little woman in a white sun hat and gloves. She introduces herself as Pidgeon Iuppa, owner and grower of Bristol Springs Viticulture. You say you’re here for the grapes.

“Well, you can buy by the pint, or…” Pidgeon’s voice trails off as she focuses on finding something in the barn. She comes back with a wide box and a grin. “You can pick as many as you want.” You and your companion’s eyes glow. This is the authentic Finger Lakes experience you’ve been craving. She hands you the box and two pairs of pruning shears and says, “I’ll join you!”

She directs you to start all the way in the back of the vineyard, where the grapes should be firmest and sweetest. “Look for the green and pink stems,” she adds. “If you finish before I get back, just give me a holler.”

Pure Finger Lakes Concord Grapes

You heed her advice and make your way to the rear of the vineyard, stopping here and there to pluck a sample. The grapes are plump and juicy and pop in your mouth with a splash of delicious tart juice. Eat your heart out, Gushers. This is candy from the earth. You clip a few bunches with green stems and add them to the box. The grapes are individual works of art in and of themselves, a hue of purple and blue peeking out from shades of green and red. The crisp fall air protects and preserves their tannic skin, forming the perfect grape for world famous grape pies. You start to shift the box back toward the barn every few feet, and realize the weight of the grapes. Maybe it’s a good time to stop. Between the two of you, you and your companion yield what you’ll later Google to learn is a peck’s worth of grapes.

Fresh, hand-picked grapes

Back at the barn, you whisper to your companion. “This is going to be like $50 worth of grapes.” You forget you’ve been conditioned to think in terms of pre-packaged pints on display in the supermarket. “We’ll make our own wine,” she offers. She’s always two steps ahead of you.

You stroll to the edge of the vineyard, looking for Mrs. Iuppa. She is all the way down at the opposite end of a row. You give a “hey” and she acknowledges with a wave. Getting the butcher’s attention at Wegman’s should be this fun, too.

At weigh-in, you are pleasantly surprised to learn your own labor pays off: at 75 cents a pound, the nine and a half pounds you picked adds up to less than any pint you can find at the store. Mrs. Iuppa offers to take a photo of the two of you holding the fruits of your labor, standing in front of an acre of grapes on top of the world in Canandaigua.

At home, you cut a slice of grape pie, pour a glass of Veltliner, and grab a bunch of grapes. You head outside to the fire pit and light up a few logs. The smoke spices the air with a potpourri of cedar, oak, and cherrywood as you watch the sun set over Conesus Lake. A boat passes smoothly and silently across the shore. Crickets trill on all sides. A mourning dove coos from the canopy of the walnut tree. You lift a glass of white wine to the Lake and whisper, “Here’s to another year.”

Ready to explore? Click below for lodging options around the Finger Lakes.