Canandaigua literally means "the chosen spot," and this charming Finger Lakes town, just 24 miles south of Rochester on the northern shores of Canandaigua Lake, is the right choice for an active but relaxing getaway. Unlike many vacation spots, it favors neither summer nor winter, but instead always has a great variety of things to see and do any time of year, including beloved annual events like the Fire & Ice Winter Festival,  Christkindl Market on the grounds of the Granger Homestead, and the Canandaigua Art & Music Festival.

Originally published 01/10/2017 | Updated 1/20/2026

FRIDAY

4 pm: Lodging with Storybook Charm

Chalet of Canandaigua Bed & Breakfast - Photo Courtesy of Chalet of Canandaigua Bed & Breakfast

Choose from over a dozen charming inns and B+B's, like the Inn on the Main or Chalet of Canandaigua (pictured). Or opt for a more full-service resort like The Lake House on Canandaigua, which even offers an on-site spa and daily wellness activities. Some accommodations offer additional special packages that add amenities like chocolate-covered strawberries, in-house massages, flowers, dining certificates, and wine tours.

6 pm: Wine & Dine with Top Chefs

New York Wine & Culinary Center Class - Photo Courtesy of New York Wine & Culinary Center

There are meals, tastings, shopping, demos, and classes to be enjoyed at New York Kitchen. On a typical Friday night, you might join the Chef's Table to help make a seasonal dish paired with one of New York State's finest wines, or hear live acoustical music served with dinner in the lakefront restaurant.

8 pm: See What’s on Tap

Twisted Rail Brewing Company - Photo Courtesy of Twisted Rail Brewing Company

Choose from up to 20 unique craft brews on tap at Twisted Rail, including a Blood Orange Kölsch, 50 Shades of Red Ale, Vanilla Cream Porter, and a Barrel Aged Vokzal Stout.

8 pm: (Seasonal) Waterfront on the Finger Lakes

The Canandaigua Lady, a replica of a 19th-century double-decker paddlewheel boat, on the lake at sunset surrounded by fall foliage

Credit: @tkystudio on Instagram

When the season and weather is accommodating, take an evening stroll along the lake, either in Kershaw Park or along Canandaigua City Pier, or embark on a scenic cruise aboard the Canandaigua Lady.

SATURDAY

10 am: Shred the Slopes & Tackle the Treetops

A family of four skis down Bristol Mountain

Get an early start to enjoy all the adventures at Bristol Mountain: 

In winter, enjoy skiing and snowboarding along with a midmorning snack of slope-side waffles and locally-crafted maple syrup at the Morning Star Cafe. For full-service snowshoeing and cross-country skiing, the Nordic Center offers snowmaking and grooming on 1.2 km of gentle, rolling hills, along with equipment and lessons.

Bristol Mountain Aerial Park - Photo Courtesy of Bristol Mountain Aerial Adventures

The mountain's Aerial Adventures are available seasonally, May-November and you can embark on the Zipline Canopy Tour, featuring seven zip lines, four bridges, and a final leap of faith. The Aerial Adventure Park adds a tightrope walk and rope ladders on seven courses with varying degrees of difficulty, including for kids as young as four years old. 

In the fall, catch spectacular views of beautiful autumn colors on a Fall Sky Ride aboard the Comet Express chairlift to the mountain’s summit.

A person wearing a white helmet while riding a wakeboard at Roseland Wake Park

To beat the summer heat, the mountain's Roseland Waterpark is the largest in the Finger Lakes with 56 acres of aquatic adventure. You can also water ski and board at the first full-sized cable wakeboarding park in the northeast.

4 pm: Explore the Canandaigua Lake Wine Trail

Snow-covered vineyard with bare vines in the foreground, a serene lake in the middle, and a large hill blanketed in snow under a clear blue sky.

Sip and savor world-class wines while soaking in beautiful vistas and rustic charm at Heron Hill Winery or pop into Acquilano Wine Cellars on Canandaigua's Main Street to sample local pours. 

6:30 pm: Local Eats & Craft Drinks

A smiling server in traditional attire holds plates of hearty food, including roast meat and mashed potatoes, in a cozy, warmly lit restaurant.

Grab a dinner back in downtown Canandaigua. Perhaps surf & turf at Nolan's; the best wurst in town at Rheinblick German Restaurant (pictured); Italian at Casa de Pasta; Authentic Mexican cuisine at Rio Tomatlan; Or hearty and casual American at Eric's Office Restaurant. In summer, consider a sunset dinner cruise aboard the Canandaigua Lady.

SUNDAY 

9:30 am: Crêpe Heaven

Crepe on a plate

Have a sinfully sweet or savory (or both) breakfast made from scratch at Simply Crepes. Beyond crepes, the menu features omelettes, French toast, breakfast sandwiches, and more. The venue even offers occasional cooking classes!

11 am: Main Street Hidden Gems

Canandaigua main street with parked cars, storefronts, trees, and colorful flowers in the foreground.

Get your shopping fix browsing the locally-owned boutiques of Main Street, from the homemade chocolates at Sweet Expressions, to the artisan oils and vinegar on tap at F. Olivers, to toys for all ages at Unique Toy Shop, to over 110 loose leaf teas along with teaware at Good Life Tea.

1 pm: Book a Spa Service

Two people relax on wooden lounge chairs inside a cozy sauna with snow visible outside. A wooden bucket and glasses sit on a bench, creating a serene ambiance.

Credit: @lakehousecdga on Instagram

Treat yourself to a massage, facial, mani/pedi, or body treatment at the Willowbrook Spa, nestled on the serene shores of Canandaigua Lake. In addition to your service, you’ll have access to the sunroom and relaxation area, heated pool and hot tub, sauna, snacks and a complimentary glass of sparkling wine. And that’s not the only spa in town! You may be interested in a wine wrap, a bamboo fusion, or a fire & ice massage with heated and cooled shells at Park West Hair Design & Spa. Or try a Vitamin C facial at Michelle's Salon & Spa at Five Seasons.

1 pm: (Seasonal) Historic Mansions & Gardens

Sonnenberg

From May through October, explore the beautiful 50-acre estate of historic Sonnenberg Mansion & Gardens (pictured). Travel back in time with a tour at the nearby Granger Homestead and Carriage Museum, featuring Victorian gardens, the largest horse-drawn carriage collection in Western NY, and five outbuildings set on a 12-acre beautifully-maintained property.

GETTING THERE

By plane: Frederick Douglass–Greater Rochester International Airport, with frequent 1 hour, 30 minute non-stop flights from NYC. Rent a car or catch a cab for the 40-minute drive to Canandaigua.

By train: Take Amtrak to the Rochester Station, then rent a car or catch a cab for the 45-minute drive to Canandaigua.

By bus: Greyhound service to Geneva Station and then a 30-minute cab to Canandaigua, or Trailways service to Rochester Bus Terminal and then a 45-minute cab.

By car:
From Albany: 3 hours
From Binghamton: 2 hours, 30 minutes
From Buffalo: 1 hour, 30 minutes
From Montreal: 5 hours
From NYC: 5 hours
From Scranton: 3 hours
From Syracuse: 1 hour, 30 minutes
From Toronto: 4 hours

Don't forget to post photos of your New York adventures on Instagram and X with #ILoveNY and #iSpyNY and tag us on Facebook!