Nestled In New York's Finger Lakes Is A Postcard-Worthy Town With A Charming Downtown And Wine Trail

Tucked in the north of New York state, near the Canadian border, lies a series of eleven lakes in a region of about 9,000 square miles known as the Finger Lakes. These long, slender lakes were created by glaciers and are a popular tourist destination for lake adventures, elegant resorts, historic towns, and fine wines. In fact, the Finger Lakes district is New York's highest-producing wine region. One of the most incredible Finger Lakes towns is Canandaigua, which means "The Chosen Spot" in the Seneca language.

Settled in the late 18th century on the northern shore of the large Lake Canandaigua, this quaint city brims with Victorian-era architecture and stunning views. Today, visitors explore the city's Main Street, with important sights such as the Sonnenberg Gardens and Mansion State Historic Park and Ontario County Courthouse. and stay at the luxurious Lake House, which commands an impressive lakefront position. The lake's fertile hillsides are lined with vineyards, and the Canandaigua Lake Wine Trail weaves through the region's best wineries.   

Canandaigua's classic charms may feel like entering a bygone era, however the city is easy to access. It is a 40-minute drive from Frederick Douglass Greater Rochester International Airport, one of the best small airports in America, which receives direct flights from many major U.S. cities. Canandaigua is also a 5.5-hour drive north of New York City and about an hour east of Syracuse. The best time to visit Canandaigua is between May and October. The summer is ideal for lake excursions, while the region's spectacular fall foliage and harvest activities make it one of the most charming destinations on the East Coast for a fall vacation.

From rich history to lake adventures to fine wines, Canandaigua is the ideal weekend getaway. One of the top attractions is a visit to Sonnenberg Gardens & Mansion State Historic Park. Tucked right off Main Street, this grand estate was built in the late 19th century and is surrounded by a series of beautiful gardens. Visitors can tour the elegant period rooms and roam the gardens, such as impressive Italianate terraces, a Japanese garden and teahouse, and a rose garden with 2,500 plants. History buffs should walk a few blocks away to the Granger Homestead, a 19th-century mansion and carriage museum. Strolling down Main Street toward the lake, you will also bypass the Ontario County Courthouse, where Susan B. Anthony's suffrage trial took place in 1873, and the Ontario County Historical Society.

At the lakefront, visit Kershaw Park, a grassy lawn and beach for an idyllic lake day, and for more active lake pursuits, head to Seager Marine, which offers boat, kayak, and paddleboard rentals. To see more of the Finger Lakes region from the water, take a cruise on the classic Canandaigua Lady Steamship replica, which offers multiple tour options. 

Back on shore, the Canandaigua Lake Wine Trail beckons, with stops at some of the area's best wineries. For the best value, purchase the $60 wine tasting passport that includes tastings at eight of the wineries on the trail. Don't miss the charming Arbor Hill Grapery & Winery, which is known for its signature Classic Traminette wine., Later, stop by the Hazlitt Red Cat Cellars in Naples, a small town that's home to the storied winery and a historic downtown. The winery is famous for its Red Cat wine.

Canandaigua's most luxurious lodging is the Lake House, a chic resort right on the lake's shores and walking distance from town. Opened in 2020, the Lake House boats 124 rooms and suites, all designed in a breezy, neutral color palette, and many offering panoramic lakefront views. The resort's restaurants – such as the Rose Tavern, known for its innovative and locally-sourced cuisine, and the dockside Sand Bar — are cozy and convivial watering holes for hotel guests and locals alike. 

Leisure lovers can relax at the Lake House's outdoor swimming pool or get a treatment at the pampering Willowbrook Spa, while active travelers can rent boats for water sports to head out on the lake. Families, couples, and groups of friends will delight at the Lake House's endless calendar of activities and convenient location to all the charms of town. "The hotel is modern, spotless and well maintained," raved a Tripadvisor reviewer. "The spa is top notch and so are the restaurants on site."

For a delicious meal off property, visit Nolan's on Canandaigua Lake, one of the area's best restaurants. Start with their famous meatballs or seafood chowder before pub fare like burgers or lobster rolls, or one of the signature steaks. Another classic eatery right on Canandaigua's Main Street is Rheinblick, known for authentic German specialties and German draft beer in a Bavarian-style atmosphere.