[itinerary | lodging] The daily grind can wear you down. Where is the motivation to keep up the hustle day in and day out? Why even bother? When every day presents the same path as before, it’s easy to forget the sandbox you live in now. But the path won’t point you in the right direction on its own. Like Alice in Wonderland — or Link in the Lost Woods — “it depends a good deal on where you want to get to.”

You kept missing it before. From a birds’-eye view, it’s easy to see how you could have. For the most part, the Finger Lakes touch a common northern shelf along the basin of the Erie Canal and US Route 20. Keuka Lake, on the other hand, is a bit of a southern mystery. Closer to Corning than to Rochester, it occupies an interesting borderland between the Southern Tier and the rest of the Finger Lakes region. What’s more than that, you might find yourself wandering around the upper outlet of the same lake twice. It’s not déjà vu — it’s just Keuka Lake’s unique Y shape. Starting from Hammondsport, the Lake flows northward until it splits into two branches that straddle northern Steuben and southern Yates Counties.

Is “branch” of a finger a mixed metaphor?

Pulteney Square

You start where the Lake begins, in a quaint but bustling village called Hammondsport. You were not prepared for the street festival that greets you, so you decide to walk around the village square. On the gazebo a brass band belts familiar holiday songs, and you catch yourself humming along like a kid on Christmas vacation. Local artisans sip hot chocolate among their wares, shooting the breeze with old friends and neighbors under tents adorned with string lights. There is a faint smell of roasted nuts and funnel cake in the air. As you stroll to the other side of the square, the village’s commercial center begins to take shape: a stately inn, a hand-packed ice cream shop, a village tavern, and even an Asian street food bistro pack Hammondsport’s downtown. You are reminded of Grass Market in Edinburgh — a tiny patch of Scotland here on the southern tip of Keuka Lake.

Scenes from Hammondsport, NY

Daylight is not a luxury at this time of year, so it’s time to continue along the path of Keuka Lake’s southern branch. You head north along the western bank, observing micro-hamlets every few miles of West Lake Road. Urbana seems aptly named. Here, a looming abandoned factory shoulders up to the edge of the road, like a Rust Belt glacier slowly decaying in the light of a new age. Flashbacks of other post-industrial cities interrupt the flow of your journey. Thankfully, Keuka Lake’s dense forests surround you and remind you of the path you chose.

Keuka Lake State Park

You find yourself at the top of the western branch, but the view of the Y’s gaping maw — a mountain splitting the Lake’s northern half in two — calls to you, its voice echoing across Keuka’s great valleys. You must navigate the full perimeter of the Lake before the sun sets. So you bypass Branchport, the village on the west branch, full speed ahead toward Keuka Lake State Park. Skeletal trees shroud your view of the water and creep fearfully toward West Bluff Drive, your only access to the very center of Keuka’s Y.

Keuka Lake’s haunting forests and steep bluffs

West Bluff Drive

West Bluff Drive is not too dissimilar from your own lakeside road. It winds between cozy cottages and mountain cabins, mobile trailers and mansions alike. But the road narrows the farther you go. Why did you go this way? You fear you’ve once again trapped yourself on a path to nowhere. The road muddies and turns uphill, climbing away from the water toward the summit of the Y. Finally, you find yourself at a crossroads: West Bluff meets East Bluff. The triumvirate of Keuka Lake’s three branches culminates in a massive seaway vista. You try to catch your breath at the top of the summit. A clear view helps you to see the different paths you could have taken.

At the crux of the Y of Keuka Lake

There’s just one problem: East Bluff Drive is blocked by a jersey barrier and a ROAD CLOSED sign. The eastern branch of Keuka will have to wait. Too dangerous to reverse down the steep and narrow path you came, you look upward and inward, where a mountain road warns of its seasonal use — no maintenance. You take a chance on the path less traveled. Despite some slush and snow, you make it to the top of the mountain and are relieved to see signs of civilization in the form of a few farmhouses and a paved road heading due north. The adrenaline rush has triggered your appetite, so you set your sights on the next village Keuka has to offer, the Yates County seat of Penn Yan.

Main Deck

Main Deck perches on the edge of the Lake in the southern outskirts of Penn Yan. A former boat hangar, the waterfront restaurant boasts fine New American cuisine in a posh but welcoming atmosphere. The host greets you warmly yet officially and leads you past a walled cabinet of wine bottles to a window-side table. Woven basket-style lanterns and wooden planks — evocative of the namesake boats of Penn Yan — are suspended from the ceiling to add to that cozy, below-deck feel.

The host immediately pours water while your server introduces herself and the specials. You are pleased to learn Main Deck stocks absinthe, so you order the New York Sazerac. While you wait for drinks, you observe the calm but electric dining room — the host brings a suspicious black suitcase over to a party of six enjoying artisan cheese trays and beer flights; on the other end, a group of middle-aged women take photos of their college-aged children using the biggest phones you have ever seen. Across the way, two professional-looking couples commiserate at the center bar. Your Sazerac arrives garnished with lemon and a nib of licorice. Your first sip is warm and fuzzy and peppery. The drink tastes the way you imagine it feels to dive into Keuka Lake on a late summer evening.

New York Sazerac and a wall of wine

You are hungry, and the menu reads like a dream. But you prefer not to commit to one path just yet. You order the NY Strip Steak as an appetizer to start — after a taste, you’ll have a better perspective on what to order next. It is at this point that the host returns, carrying the black suitcase like before. You scoff: an obvious MacGuffin, like in Pulp Fiction, right? He opens the case, and instead of an orange glowing light that would make Vincent Vega exclaim, “Yeah, we happy,” it’s an array of steak knives. Not just plain silver knives, but knives of varying lengths, shapes, and handles. “Choose wisely,” the host says.

You select a knife with a ridged, birchwood handle.

“Excellent choice,” he grins. It’s the first time he has smiled all night. The steak arrives and you take your chosen knife for a test drive.

The meat is succulent, crisply charred, and flavored richly. You couldn’t be happier with your choice. The accompanying broccolini is sweet and buttery, while the mashed parsnip adds an extra layer of texture to every bite. The tangy in-house steak sauce gives A-1 a run for its money.

You stand at another turning point, a fork stuck in the road. On one hand, the Double Smashburger prepared by a gourmet chef makes you feel like a character in that movie, The Menu. On the other hand, you couldn’t pass up the opportunity for a full Lobster Tail. Which path do you take? Like Keuka Lake, you break both ways. The Smashburger is packed tightly into a lightly toasted, seeded bun, its gooey cheese and homemade burger sauce binding the sandwich together. The fry seasoning packs a nice kick. But the path of the Lobster Tail leads you to the real treasure: buttery soft lobster meat and hearty green pea rice get cozy with each other on a bed of nantua sauce for a flavor explosion on your tongue.

Lobster Tail Rice; NY Strip with Broccolini; Double Smashburger with Fries

Main Deck gives you the inspiration you need to walk the path another day. Satisfied with your meal and your experience, you step out into the cold darkness of January’s long night. There is only one path you want to take at the moment, and that’s the quickest way home to bed.

Why Keuka Lake? Because its shape and location transcend upstate New York’s sub-regions. The Lake is a tuning fork being struck against the Southern Tier, its mysterious tones resonating northward toward big sisters Canandaigua and Seneca and outward toward Central and Western New York. And if you listen to the Lake — and choose the path wisely — you just might find where you wanted to get to.

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