Spontaneous Saturday in Canandaigua NY

[jump to itinerary] Upstate New York in May can be absolutely gorgeous. It’s been a long winter, but summers here are worth the wait. The sun moves you to get up on a Saturday and hit the road. No plan. No specific destination. Just driving east from one Lake to the next. You and your travel companion live to be spontaneous. In the paradise that is New York’s Finger Lakes, you can’t go wrong no matter which direction you take.

Life has pulled you in multiple directions, too. One door closes and another opens. Memories of a past life in a rusty industrial city begin to fade; visions of a green, glowing future grow brighter. And your new little companion grows bigger. You can see her in your dreams. You can feel her tiny fists, urging to join in on the adventure. You re-frame your travels now: what new places will you explore with a little one in tow? What new activities will you get into? What new friends will you make?

Canandaigua has always been a good friend to you. Within the first week of moving to Conesus Lake House, you strolled through Kershaw Park one humid evening, the Lake lights flickering like Manhattan’s night sky. You ventured deep into Canandaigua’s wilds to visit a folk-art commune, and you lost yourself in the mountains along Bristol and Italy Valleys. Canandaigua looms from every vantage point along Routes 21 and 364, stretching like the Bosphorus Strait from sea to sea. An ocean in the middle of a giant farm.


Kershaw Park at the northern tip of Canandaigua Lake, NY

So you stop at Kershaw Park again, teeming with life and sounds and fragrances. Gulls and songbirds call to each other from the trees. Flowers bloom and buzz with the sound of pollinators. The waters calmly lap at Canandaigua’s shore. You walk hand in hand with your companion east through the park, passing the pavilion and the public beach, which — though clean and pristine and ready for swimmers — is not quite open for the season. You stop at a playground and study the various child carriers and strollers, mentally comparing them to the new equipment you’ve acquired recently.

You eventually arrive at a long pier with mooring stations, just outside the patio of the Hotel Canandaigua. A fisherman casts off on one while a family of tourists take in the view from another. You settle down on the last dock, and your companion kicks off her shoes. The water is clear enough to see the rolling lake sand beneath, but looks can be deceiving: the docks are quite far above the water, making it somewhat difficult to dip her toes. Canandaigua is such a tease.


Flirting with the lake, are we?

Further east, you spy an old-fashioned paddle-wheel boat mooring on an exclusive pier. It’s the famed Canandaigua Lady, a cruise boat you’ve heard about from your adventures in social media. You imagine the ride to be similar to a ferry you used to ride back and forth in New York’s harbor, the lifeline between Staten and Manhattan islands. Another memory eroding like a fossil in the sandstone of time. And like fossils buried underground, a new layer of earth must be laid down. You will make new memories with a different boat, this time with your new little companion there to elevate the experience.


Whoa whoa whoa, she’s a lady!

You take a moment to look around the shore and deeper into the Lake itself. It might be the first time you’ve gotten this intimate with the water’s edge since moving to the Finger Lakes. You are mesmerized by the Lake’s floor and how closely it resembles the ocean’s sands. Occasional seaweed, tiny pebbles, shells, and– a car?


Hot Wheels sleeps with the fishes.

If the analogies to New York’s harbor are any indication, it’s no surprise someone wanted to dispose of unwanted baggage in the Lake. Toy car or not, the message is clear as Canandaigua’s water. Staring down at your reflection, you take time to reflect on your life as well. Time to dump the complicated memories of the past deep beneath the surface, where no one can ever find them again. But even Tony Soprano couldn’t shake the image of his dear friend Salvatore “Big Pussy” Bonpensiero after that fateful day on the boat. “Anyway,” his fishy friend says in a dream, “four dollars a pound.”

Still, the Lake helps you to forget and to move on. You have too much on your plate to get bogged down by the details of your past. It’s time to pick yourself up, brush yourself off, and become the man your daughter needs you to be. So while there’s still time, you decide to have another round at the conveniently located Twisted Rail Brewing Company, right across from the docks.


And she’s buying a stairway to heaven — at Twisted Rail Brewing Company, Canandaigua, NY

With an open door and a sunny patio, Twisted Rail invites you to come on in and have a beer. Several parties have camped out on the patio, and there’s a line of what appears to be a bachelorette party when you get in. You’ve learned from your adventures that lines are good indicators, so you wait it out while your companion looks for the perfect table to set up shop. Immediately upon entering Twisted Rail, there is a small but cozy wooden bar where a gentleman presently sips a tall draft. When it’s finally your turn to order, you request a light beer in a pint glass. The beer is liquid gold in your hands as you meander outside to the back patio, where your companion appears to have the place to herself.


A private back patio for you and your companion

Twisted Rail’s property abuts the Canandaigua Outlet, a creek that ultimately flows into the Erie Canal. A boisterous willow tree dips its branches into the creek beside your seat while fishers occupy the banks of the outlet, hoping to snag any of the tiny fish making bubbles on the surface of the calm water. You take in the scene and note the small stage and satellite bar out back, quiet at the moment but certainly lively on a Saturday night. You make peace with the fact that your Saturday nights will focus inward and homeward for a while. You’ll have a new mama and a new baby girl to take care of. And while she can’t drink it, this soon-to-be-mom holds up your beer for the camera. Like you, she simply can’t resist getting the perfect shot.


Brewed from New York State grains

You thought a lot about sinking the baggage of the past, but it’s important to remember how far you’ve come and what you’ve accomplished, too. From becoming one and growing together with your travel partner, to finding and creating Conesus Lake House, to preparing for the birth of your first child: if someone had told you 10 years ago that you would be sitting here, in this paradise, with a cold beer, a loyal companion, and a beautiful daughter on the way, you would have laughed them out of the room. Like Marty McFly says in Back to the Future: “If you put your mind to it, you can accomplish anything.”


Brew and a View from Twisted Rail

Feeling like your old self again, you remember your purpose: to explore, to write, and soon, to give life to a little girl named Adelaide. You’ve enjoyed this spontaneous Saturday in Canandaigua and look forward to many more with Addy next to you. Her smile, her shiny eyes, her laughter — these will be your new inspiration, your muse. Everything you do, you’ll do for her.

So you head back through Kershaw Park, reinvigorated and repurposed. Do not dwell on the past, young padawan— but be present in the moment. You catch yourself talking to, well… yourself. You realize you’ve been doing it this entire time. Why is that? Could it be you’re trying to separate the old self from a new self? After all, you’re a Gemini, and your 40th is coming up in a matter of days. Maybe it’s time for the Great Twins to de-couple from each other once and for all.


“Back in the ‘90s…”

Before reaching the car, you pause at a horse statue perched along the path of Kershaw. Some days you feel like Bojack Horseman, the washed up, wannabe serious actor who peaked in the ’90s. Is your second-person persona too pretentious? Did you lean on it too much as a hook, a gimmick? Reflection can lead to growth, moving you to stop dwelling on yesterday and to look instead toward tomorrow. You are entering a new era of life, you and your travel companion. Your travel days might be on hiatus for a little while. How will you write the next chapter? And what will you write about instead?

“Write about Adelaide,” your companion grins.

So I will.


Today’s Travel Itinerary

Road time:

  • First leg: Conesus Lake House to Kershaw Park in Canandaigua, NY || 29 mi.; 38 min.
  • 2nd leg: Kershaw Park to Twisted Rail Brewing Company in Canandaigua, NY || 0.2 mi.; a short walk
  • Last leg: Twisted Rail Brewing Company to Conesus Lake House || 29 mi.; 38 min.
  • Total mileage and drive time: 58 mi.; 1 hour, 17 min.

Special places:

  • The Canandaigua Lady, Canandaigua, NY || The Canandaigua Lady is a 19th century steamboat replica and Mississippi-style paddle wheel boat, the kind Tom Sawyer would have stolen aboard in a Mark Twain novel. Open May through October, the cruise line offers lunch, dinner, and excursion cruises for all ages.

Food and drink:

  • Twisted Rail Brewing Company: 1 craft beer, $6.40

Petrol stops:

  • None needed on this trip.

Total time & money spent:

  • 2 hr., 17 min. and $6.40 plus tips.

Want to experience this trip yourself? Click the button below for booking information.

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