Canandaigua Travel Guide: How to Spend a Perfect Weekend in the Finger Lakes

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Plan the perfect Finger Lakes weekend with this Canandaigua travel guide featuring food, wine, and scenic stops.

Some trips ease into your memory with a gentle hum—quiet streets, warm meals, and kind conversations that linger long after you’ve returned home. My getaway to Canandaigua, tucked along the northern edge of its namesake lake in New York’s Finger Lakes, did exactly that. I came expecting great wine and scenic landscapes; I left genuinely moved by the heart, history, and hospitality of this small lakeside town.

A Warm Welcome in the Heart of Town

I arrived on a balmy September afternoon and checked into the Bed & Breakfast at Oliver Phelps, a gracious historic home that immediately wrapped me in comfort. Something is grounding about staying in a centuries-old inn—wooden floors that creak softly, antique touches that whisper stories, and the easy cadence of innkeepers who know their town like family.

After settling into my room, I chatted with innkeeper Karin Koepcke about the history of the home. Boasting lovely Greek revival architecture, it dates to 1813 with an 1830 expansion. I loved the twelve-foot ceilings, wide-plank floors, and blown-glass windows. It was a family home until 1928, when it became part of the Christian Science Church until 1977, when it opened as the first bed and breakfast in Canadaigua.

My room looked out over lovely gardens and a gazebo. I spent a little time catching up on some work, but the smell of baking cookies and the beautiful September skies beckoned me. I headed downstairs to ask Karin for recommendations on what to do for the rest of the afternoon.

Karin asked me about my breakfast preferences the next morning, showed me how to get in if the door was latched when I returned, gave me referrals for dinner spots, and I set out to explore downtown Canandaigua. It was what you hope for when visiting a lake town: leafy streets lined with beautifully preserved old homes, boutiques with thoughtfully curated displays, and locals greeting each other with familiarity.

Wandering Canandaigua

I wandered without an agenda, letting the town reveal itself slowly—porches overflowing with late-summer flowers, bits of Victorian architecture peeking out from behind trees, and storefronts filled with handmade goods begging to be admired. I stopped to read a plaque that announced that Alexis de Tocqueville had visited as a 25-year-old during his 1831 tour of America, while promoting his book, Democracy in America.

By dinner, my appetite matched my curiosity, so I headed to the restaurant Karin recommended and grabbed a table at Simply Crêpes. The café feels charming and unfussy, the kind of place where comfort food meets simple elegance.

I ordered a Bellini to ease into the evening, followed by a Chicken Cordon Bleu Crêpe—warm, savory, a little indulgent, and precisely what I needed after a day of travel.

But dessert stole the show: a Strawberry-Nutella crêpe that reminded me why life is better when you say yes to sweetness.

A Morning with Local Flavor

The next morning began with breakfast at Oliver Phelps—house-made, nourishing, and proof that B&B owners know how to start your day right. I loved that Karin began each morning with a shot of locally made kombucha. She served up Komorebi Kombucha from nearby Naples. I had Tumeric Ginger and it was a great start to my day. After a full, home-cooked breakfast, I enjoyed conversations with fellow guests over a second delicious cup of hot coffee before setting out for the first stop on my itinerary: New York Kitchen. There, I met up with another food, wine, and travel writer, and we prepared for a weekend of fun exploring the area.

Perched proudly on the lakefront, New York Kitchen is a celebration of all things grown, raised, brewed, and crafted in the state. My tour began with a wander through their state-of-the-art culinary facility. Stainless steel, warm wood, and a flurry of delicious smells set the mood. I wish I could return for a class, but I loved learning how the space hosts chefs, educators, and curious food lovers year-round.

I really loved the Junior Chef Initiative, which engages local youth in a “safe, hands-on learning environment” designed to promote teamwork and creativity through the culinary arts. To have a chance to experience the love of food at such a fantastic facility would have been a dream when I was a kid—who am I kidding, it would be a dream to take classes there now!

From there, we stepped into the tasting room—all New York, all the time. At any given time, they feature more than 60 New York wines, along with a rotating selection of seasonal New York craft beers and ciders. They also serve locally made distilled spirits and non-alcoholic beverages.

I was there for a wine tasting, so I started with the 2018 Little Clover Riesling Extra Brut Sparkling from Seneca Lake, its crisp profile cutting through the late-morning humidity. Lovely acidity. Clean bubbles. A reminder that New York does sparkling wines extremely well. Then came a classic: the Dr. Konstantin Frank 2023 Grüner Veltliner. Fresh, elegant, and beautifully balanced, the wine offered the kind of citrus-driven brightness that makes Grüner such a natural fit for the Finger Lakes. My Finger Lakes wine tasting was off to a delicious start.

A Taste of Naples: Roots Café and Inspire Moore Winery

By late morning, we made the drive to Naples, a small community known for its farm-to-table food and easygoing charm. Lunch at Roots Café felt like stumbling into a local secret.

I ordered the Apricot Chicken Sandwich: wine-poached chicken breast layered with melted brie and topped with a house-made apricot-thyme chutney, all tucked between toasted West Hollow sourdough. Sweet, savory, herbaceous—it was a perfect midday treat. I also enjoyed yet another Komorebi Kombucha. I think it’s evident that this part of the Finger Lakes really loves showcasing its own products.

Right next door sits Inspire Moore Winery, where the philosophy is simple: thoughtful wines with a soulful backstory. The gals pouring wine welcomed us with a relaxed, open-door warmth that immediately made the tasting feel more like a conversation than a formal experience.

We grabbed seats outside on the covered patio, looking out at the vineyards, and settled in to sample some unique wines.

I started with the sparklings—2024 Unsupervised, a Cayuga Pétillant Naturel with a playful energy, and the 2021 Pinot Noir Brut Cuvée, a traditional-method blanc de noir aged 18 months in tirage. The latter opened with notes of white fruit and light florals, clean and expressive.

From there, the tasting became a parade of personality. GRACE, a rosé of St. Laurent, offered watermelon and strawberry on the nose with a bubblegum finish that felt cheeky and fun. LUST, a Pinot Noir, brought earthiness—forest mushrooms, red fruit, and a softness that lingered. And LEVITY, a rosé of Pinot Noir Petillant Naturel, added a touch of spice to its bright berry notes. This was unlike the pinot noirs of the Pacific Northwest I’m used to, but I enjoyed the Finger Lakes terroir evident in this Pet Nat.

Before leaving, we stopped at one of the scenic overlooks in Ontario County—an open sweep of lake and rolling hills that reminded me why the Finger Lakes region captures so many hearts. I soaked it up and felt disappointed that I didn’t have more time to enjoy the area.

Vines, Views, and a Dance of Flavors at Heron Hill

Our next stop was Heron Hill’s tasting room on Canandaigua Lake, where we wandered directly into the vineyards for a firsthand look at the fruit behind the bottles. There’s something grounding about touching the vines, hearing winemakers speak about the land, and looking across a landscape that shapes every sip. After wandering through the vines and hearing the story of owners John and Josephine Ingle, we were ready to step back inside for a tasting.

We began with the 2021 Unoaked Chardonnay from Ingle Vineyard—bright, crisp, with lemongrass and green apple leading the way. Next came the 2021 Riesling from the same vineyard, a delightful blend of apple, lemon, melon, and spring blossoms. Dancing Bear White Pinot Noir and the Bubbly Blaufränkisch Rosé followed—playful, expressive, and well-suited to the breezy afternoon. I enjoyed the Dancing Bear wines, a new line that is “all about having fun and breaking the rules.” These wines are designed to entice a younger generation, and I found them playful and different. A bottle of the Dancing Bear White Pinot Noir made its way home with me.

The reds rounded out the tasting: the 2020 Cabernet Franc from Ingle Vineyard and the 2020 Reserve Red, both offering depth, structure, and a welcome contrast to the lighter wines that preceded them. These were both classic wines that also made their way home with me. I ended up enjoying the 2020 Cabernet Franc for my anniversary with a lovely prime rib dinner.

A Lakeside Stay to Remember

Late afternoon, we gathered at the Lake House on Canandaigua, a property that embodies everything a lakeside retreat should be—light-filled spaces, warm wood, modern touches, and a sense of calm that settles over you the moment you walk in.

Our pre-dinner tour of the property revealed a space designed with intention: rooms that bring the outside in, gathering areas that encourage conversation, and an effortless connection to the lake. It’s one of those hotels where you instantly think, I could stay here for days.

Although I didn’t stay at the property on this visit, I recommend it if you prefer a resort to an inn. While my B&B was so welcoming, Lake House is a different experience. I was intrigued by the spa treatment rooms, and the lakefront vistas are breathtaking.

We watched an afternoon storm roll in as we wandered the grounds and while we ate dinner, and it was an experience to remember.

Dinner followed at Rose Tavern—a serene evening filled with good food and stunning water views. We ate out on the covered patio, which gave us unobstructed views of the water. Rolling clouds and a summer downpour replaced the streaks of evening sunlight as we talked about wine, travel, and the region’s charm.

And because no perfect travel day should end early, we wandered to Pintxo Wine & Tapas after dinner. With its intimate atmosphere and smart wine list, it was the ideal nightcap. Conversation flowed easily over shared bites, and I felt that rare travel-writer satisfaction: a day well spent, stories already forming, and the quiet joy of feeling connected to a place.

Morning Reflections and a Fond Farewell

Saturday morning brought one final breakfast at Oliver Phelps—another comforting meal, another moment to appreciate Karin’s thoughtfulness, and the relaxed pace that Canandaigua seems to inspire.

As I packed to leave, I realized the trip had covered all the things I love most: meaningful food experiences, conversations with winemakers who care deeply about their craft, the slow rhythm of small towns, and the steady pull of a beautiful lake at every turn.

Canandaigua is more than a waypoint on the map of the Finger Lakes. It’s a destination with its own identity—historic, flavorful, and endlessly welcoming. It’s the kind of place that invites you to wander, savor, and come back when you need a reminder of how rejuvenating travel can be.

And yes—I’ll be back.

Looking for more great wine destinations? Check out Wander With Wonder for more of our favorite wineries and more places to explore if you travel to New York.

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