A Town That Looks the Part
Canandaigua’s Main Street runs wide and straight through the center of town, lined with 19th-century commercial buildings that have been maintained rather than merely preserved. This is not a downtown kept alive by nostalgia — it functions. Independent shops, restaurants, a performing arts center, and the Ontario County Courthouse (where Susan B. Anthony stood trial in 1873 for the crime of voting) occupy storefronts and civic buildings that have served the community continuously for over 150 years. With a population of roughly 10,000 in the city proper and more in the surrounding town, Canandaigua is the largest community on any Finger Lake and carries itself with the confidence of a place that has always been the center of something.
The Susan B. Anthony Trial
On June 17, 1873, Susan B. Anthony stood before Judge Ward Hunt in the Ontario County Courthouse on Main Street, charged with “illegally voting” in the 1872 presidential election. She had cast her ballot at a barbershop in Rochester the previous November. The trial was moved to Canandaigua because Anthony’s activism had made impartial jury selection impossible in Rochester. Judge Hunt directed a guilty verdict without allowing the jury to deliberate — a procedural outrage that Anthony used to fuel the suffrage movement for the next three decades. The courthouse still stands at 27 North Main Street, a working judicial building with a second-floor courtroom that looks much as it did in 1873.
Sonnenberg Gardens and Mansion
Sonnenberg Gardens is a 50-acre estate on North Main Street that contains nine formal gardens, each in a different style — Japanese, Italian, Rock Garden, Rose Garden, Pansy Garden, and others — surrounding a 40-room Queen Anne mansion built in 1887. The gardens were created by Mary Clark Thompson between 1902 and 1919 and represent one of the most intact surviving examples of Victorian-era garden design in the United States. The estate is open from May through October. Admission runs around $15 for adults, and a thorough visit takes two to three hours. The Moonlight Stroll events on select summer evenings, when the gardens are lit by luminaries, are among the most atmospheric events in the Finger Lakes.
The Waterfront
Canandaigua Lake stretches 15.5 miles from the city’s northern shore to the village of Naples at its southern end. The lake is the fourth largest of the Finger Lakes and one of the cleanest — the Canandaigua Lake Watershed Council has kept development pressure in check, and the water clarity remains exceptional.
Kershaw Park occupies the city’s lakefront at the foot of Main Street. The park includes a public swimming beach (open Memorial Day through Labor Day, free for residents, small fee for non-residents), a large grassy area, a playground, and a pier that extends into the lake. The Canandaigua Lady, a replica paddlewheel steamboat, departs from the adjacent City Pier for narrated lake cruises from May through October.
Food and Drink
New York Kitchen (formerly the New York Wine and Culinary Center) sits on the lakefront near Kershaw Park. It is part cooking school, part tasting room, part restaurant, and part culinary education center, offering hands-on classes, wine and beer flights from across New York State, and a menu built around local ingredients. The facility was designed as a showcase for New York agriculture and food production, and it delivers on that mission with specificity — tastings are organized by region, and the instructors know the producers personally.
Downtown dining includes Rheinblick German Restaurant (schnitzel, spaetzle, and a German beer list in a converted Main Street storefront), Rio Tomatlan (Mexican cuisine that draws diners from across the region), and Nolan’s on Canandaigua Lake, a waterfront spot with a sprawling deck and lake views. For coffee, Whimsy Bakery and Cafe on Phoenix Street produces pastries and espresso that have earned a loyal local following.
What to Do
- Main Street shopping: Independent boutiques, antique shops, and specialty stores line both sides of the street. The Cheshire Union on Coach Street offers a curated mix of home goods and gifts in a renovated historic building.
- CMAC (Constellation Brands-Marvin Sands Performing Arts Center): A 15,000-capacity outdoor amphitheater on the grounds of Finger Lakes Community College, hosting major touring acts from June through September.
- Granger Homestead and Carriage Museum: A Federal-era home (1816) with a collection of over 70 horse-drawn carriages and sleighs. Open seasonally.
- Lake paddling: Canandaigua Lake is excellent for kayaking and stand-up paddleboarding, with rentals available at the City Pier area during summer months.
- Finger Lakes Gaming and Racetrack: A harness racing facility and gaming floor located just east of the city on Route 332.
FLX Finest Award Winners
The FLX Finest awards are the region’s readers’ choice competition — voted on by the people who actually live here. These are not critic picks or social media darlings; they are the restaurants, bars, and experiences that Finger Lakes residents choose with their own ballots, year after year. These are Canandaigua’s Gold winners.
Nolan’s on Canandaigua Lake
Steakhouse '22–'25Seafood Restaurant '22–'25Fine Dining Restaurant '22–'25There is a short list of Finger Lakes restaurants where the setting alone justifies the price, and Nolan’s is at the top. Sitting directly on Canandaigua Lake about three miles south of downtown, the sprawling deck lets boats pull right up to the dock for dinner in summer. Gold or Silver for Best Steakhouse, Best Seafood, and Best Fine Dining every single year since FLX Finest began in 2022. The steaks are the headliner, the lobster mac and cheese has a cult following, and the west-facing orientation means sunset is not a happy accident — it is the main event.
This replica 19th-century double-decker paddlewheel steamboat has earned Gold for Best Lake Cruise two years running (2024-2025). Departing from the City Pier at the foot of Main Street from May through October, the Canandaigua Lady offers lunch, dinner, and excursion cruises on one of the cleanest Finger Lakes. The two-hour dinner cruise at sunset, gliding past the forested eastern shore while the western hills catch the last light, is the kind of thing you do once and then start recommending to everyone you know.
Dave and Rita’s sits on Route 96A in Romulus, between Seneca and Cayuga Lakes, and from the outside it looks like a small roadside bakery you might drive past if nobody told you to stop. Inside is a different story. Gold for Best Bakery in 2022 and 2023, with consistent recognition for Best Cookies. The cookie case is the main event — thick, buttery, soft-centered, in enough varieties that choosing fewer than four feels like a failure of ambition. Wine trail visitors stumble in once and build it into every subsequent trip.
Simply Crepes started with a family recipe from a dairy farm in rural Quebec — co-founder Pierre Heroux’s grandmother cooked crepes on buttered cast iron with whatever was good that morning. The Canandaigua location on South Main Street won Gold for Best Brunch in 2022 and has held recognition every year since. Savory crepes wrap local goat cheese and roasted vegetables in properly thin, golden-edged packages; sweet crepes lean on real Quebec maple syrup. Arrive early on summer Saturdays or accept the wait.
Chef-owners Kimberly Vakiener (the Ki) and Alexander Bacon (the X) opened in the former Gleason’s space on South Main Street and turned it into something Canandaigua didn’t have before — a restaurant that takes food seriously without taking itself too seriously. Gold for Best Burger and Best Fine Dining, Silver for Best All-Around Restaurant. The rooftop deck is one of the best outdoor dining setups in the region, the creative American menu rotates monthly, and OpenTable recognized them with Diners’ Choice awards in both 2024 and 2025.
Finger Lakes Public House took Gold for Best Bloody Mary in 2025 after climbing from Silver the year before. Crafted with house-made mixes and bold garnishes that turn a standard brunch cocktail into a proper production, the Bloodys here have earned a loyal following among locals who treat Sunday morning as a competitive sport. The hearty pub fare and relaxed atmosphere round out a spot that works equally well for a weeknight pint or a weekend hair-of-the-dog.
Practical Details
Canandaigua sits at the northern end of Canandaigua Lake, approximately 30 miles southeast of Rochester via I-90 and Route 332. Main Street has metered parking (enforced on weekdays) and several free municipal lots on side streets. The city is walkable from the courthouse to the lake — a straight 10-minute walk down Main Street. Peak season is June through October, but Canandaigua maintains year-round activity thanks to its size and the presence of Finger Lakes Community College.
Locals Know
The best view of Canandaigua Lake is not from the waterfront — it is from the top of the hill on Route 21 heading south toward Bristol, where the entire lake opens up below you in a single sweep. And if you are visiting Sonnenberg Gardens, check the schedule for their Garden Concert Series in July and August, when local musicians perform in the gardens on Thursday evenings — it is the most pleasant way to spend a summer night in the Finger Lakes.