Canandaigua, New York, known as “The Chosen Spot,” carries a rich past and a distinctive character. The name comes from the Seneca word “Ganandogan,” reflecting its importance to the Haudenosaunee Confederacy before European settlement. The city played a key role in early American history, serving as the site of the 1794 Treaty of Canandaigua, which established peace between the U.S. government and the Six Nations. Today, Canandaigua’s population is approximately 10,994, and the city maintains a deep connection to its heritage while offering a mix of modern attractions, historic sites, and lesser-known oddities.
Sonnenberg Gardens and Mansion State Historic Park stands out as one of the few remaining estates from the Gilded Age in the region. This 50-acre property, originally the summer home of banker Frederick Ferris Thompson and his wife Mary Clark Thompson, features a Queen Anne-style mansion surrounded by meticulously curated gardens. Each garden reflects a different international style, from an elegant Italian-style courtyard to a Japanese-inspired landscape with a koi pond. The mansion itself, with its original furnishings, offers a look into the opulence of the early 20th century. The estate’s wine center, housed in the former aviary, showcases the area’s winemaking history.
The Canandaigua Lady, a replica 19th-century paddlewheel steamboat, provides an uncommon way to experience the lake. This double-decked vessel offers cruises that recreate the type of transportation used during the steamboat era of the Finger Lakes. Passengers can enjoy themed excursions, including murder mystery nights and historical narrated tours that highlight the lake’s past, including its rumored ties to prohibition-era smuggling.
A lesser-known attraction in Canandaigua is the Octagon House, a private residence built in the mid-19th century. Octagonal houses were briefly popular due to the belief that their shape provided better natural lighting and ventilation. Though not open to the public, the house remains an architectural curiosity. Another distinctive piece of history lies in Woodlawn Cemetery, where Gideon Granger, the nation’s longest-serving postmaster general, is buried. His influence extended beyond mail service—he helped shape early American infrastructure.
Canandaigua’s supernatural lore adds to its intrigue. The Seneca Point area along the lake is said to be haunted by a “Lady in White,” a spectral figure who allegedly searches for her lost child. Some locals claim to have seen her drifting through the mist on quiet nights. A more tangible yet eerie site is the historic Ontario County Jail, where infamous criminal William Fee was hanged in 1865. Visitors have reported unexplained cold spots and ghostly whispers within the building’s walls.
One of the area’s most anticipated events is the Finger Lakes Plein Air Festival. This gathering brings nationally recognized artists to Canandaigua to paint its landscapes in real time. Visitors can watch artists create their pieces and even purchase fresh works. Another major event is the Fire & Ice Winter Festival, which features professional ice sculpting, fire performances, and horse-drawn carriage rides through downtown. The combination of extreme cold and fiery displays makes for a unique seasonal spectacle.
For a deeper dive into regional cuisine, New York Kitchen provides interactive culinary experiences focused on locally sourced ingredients. Visitors can take cooking classes, sample Finger Lakes wines, and learn about the region’s agricultural bounty. The facility showcases New York’s diverse food culture through chef-led tastings, hands-on workshops, and special dining events.
Canandaigua’s dining scene includes a mix of longstanding favorites and newer culinary ventures. Nolan’s on Canandaigua Lake serves premium steaks and seafood in an upscale setting, offering dishes like bourbon-glazed salmon and prime rib with au jus. Rheinblick German Restaurant brings an authentic taste of Bavaria to the region, featuring dishes such as jägerschnitzel and käsespätzle, paired with imported German beers.
Unique local businesses in Canandaigua include The Unique Toy Shop, which has been a staple of Main Street for decades. Unlike big-box stores, it specializes in handcrafted and educational toys, along with hard-to-find vintage games. Another one-of-a-kind spot is Liberty Cottage, a boutique offering an eclectic mix of home decor, antiques, and artisan goods. The shop is housed in a charming historic building, adding to its character.
For outdoor enthusiasts, Kershaw Park provides public access to Canandaigua Lake with a sandy swimming beach, a boat launch, and picnic areas. The park’s scenic walking trails offer views of the lake and surrounding hills, making it a popular spot for both relaxation and recreation. Meanwhile, Bristol Mountain, located a short drive away, offers year-round activities, including skiing in winter and zip-lining in summer. The mountain’s 1200-foot vertical drop is the highest in the region, drawing winter sports enthusiasts from across the state.
An unusual annual gathering in Canandaigua is the Pageant of Steam, a massive display of antique steam engines, tractors, and industrial equipment. Hosted by the New York Steam Engine Association, this event draws enthusiasts who appreciate the engineering feats of the past. Visitors can see fully operational steam-powered machines in action, from threshers to locomotives, and even take rides on some of the vintage equipment.
Canandaigua’s artistic side is reflected in its collection of galleries and public art installations. The Pat Rini Rohrer Gallery showcases work from regional artists, specializing in landscapes that capture the beauty of the Finger Lakes. Meanwhile, the city’s streets feature a variety of murals and sculptures, including a striking depiction of Canandaigua Lake painted on the side of a downtown building. Public art projects continue to expand, with local artists contributing to the evolving aesthetic of the city’s public spaces.
A lesser-known fact about Canandaigua is its connection to Hollywood legend Humphrey Bogart. The actor spent childhood summers on Canandaigua Lake, where his family owned a cottage near Seneca Point. Though Bogart later became synonymous with classic film noir, his early years were shaped by the calm waters and wooded shores of the Finger Lakes. His family’s presence in the area is a piece of local history that film buffs appreciate.
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