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A 4-Day Road Trip in New York's Finger Lakes Region

Winery-hop by boat and work up an appetite on waterfall-dotted trails

Upstate New York road trip map

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Your first day on this four-day adventure includes about 4 1/2 hours of driving northwest from New York City, but you'll take it slow — and the rest of your trip will focus on a smallish area of the beautiful Finger Lakes region, a haven for wine and nature lovers. That means that if you'd rather not jump to different accommodations each day, as this itinerary suggests, you could just as easily spend the first two nights in Watkins Glen and the next two in Ithaca ("Ithaca is Gorges,” as its motto boasts), before spending your last day in Aurora on Cayuga Lake. And consider this trip for fall, when you'll find particularly stunning scenery in this region.

COVID-19 update

The unpredictability of the coronavirus outbreak means travel restrictions are constantly evolving. Be sure to check New York's official website for updates before visiting from out of state, and follow Centers for Disease Control and Prevention guidelines for safe travel.

Hammondsport, NY country road

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Hammondsport

Day 1: New York City to Hammondsport (283 miles)

The drive upstate via Interstate 80 westbound, Interstate 81 north and Interstate 86 west transports travelers from urban jungle to bucolic landscapes. From I-86, take exit 46 and stretch your legs in the town of Corning, home to the world's largest glass collection. The Corning Museum of Glass is a must-visit (advance tickets currently required due to the pandemic), with 50,000 objects representing 3,500 years of glass history. Browse the boutique shops, art galleries and studios of Corning's Gaffer District, then lunch at the restaurant at Bully Hill Vineyards. If you're a meat lover, you won't want to miss the barbecue, slow-smoked for up to 16 hours over locally sourced applewood.

Hop back on I-86 and continue on to Hammondsport. Situated at the foot of Y-shaped Keuka Lake, this village of about 650 residents has been touted by the website Budget Travel as the “Coolest Small Town in America.” It's also home to some of the Finger Lakes’ top wineries. The Dr. Konstantin Frank Winery pays tribute to the man who introduced European vinifera wine grapes to upstate New York. The new, indoor-outdoor progressive tasting experience must be prebooked and is limited to groups of six or fewer.

Where to stay: The complimentary breakfast is reason enough to book one of the four Victorian-inspired rooms at the chef-owned Pleasant Valley Inn, just outside Hammondsport. Savor LaColombe coffee, cheddar-and-bacon scones and French-style scrambled eggs from a spacious patio overlooking vineyards.

Fall grape vineyards on Seneca Lake in the Finger Lakes region of New York state

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Seneca Lake

Day 2: Hammondsport to Watkins Glen (20 miles)

After an indulgent breakfast at the Pleasant Valley Inn, you'll want to walk off your food coma. Head north on Route 54 and then east on County Roads 87, 114 and 23 to reach Watkins Glen State Park. The popular Gorge Trail follows Glen Creek 1.5 miles through a 400-foot-deep gorge, passing through caves and 19 photo-worthy waterfalls. The trail itself climbs gradually, but a basic fitness level is recommended (and sturdy sneakers) as you'll walk up more than 800 stone steps. Park officials request that visitors wear masks.

The Finger Lakes region is known for its wine, but it's also home to some excellent craft breweries. Grist Iron Brewing, less than 10 minutes away in Burdett, one of the innovators, experiments with barrel-aged and sour brews. Order a growler to go or pair suds with pub food such as buffalo chicken pizza and beer cheese tater tots (socially distanced indoor and outdoor seating and contactless checkout are part of new safety procedures). Save room for a scoop (or two) from a family-run ice cream parlor, the Great Escape, in Watkins Glen. Classic and inventive flavors (Teaberry, Holy Cannoli) are all made in house, and you can place your order at a new walk-up window.

Where to stay: The 104-room Watkins Glen Harbor Hotel has an unbeatable location on Seneca Lake, walking distance to the state park. Certain services, such as turndown, have been suspended due to COVID-19; others, like alfresco lakeside dining, have been beefed up.


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Cascadilla creek gorge waterfall trail, Ithaca, NY,

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Cascadilla Gorge Trail

Day 3: Watkins Glen to Ithaca (25 miles)

Drive along Route 79 east to Ithaca. Pick up a picnic lunch of creative sandwiches, such as the Empire Combo (pastrami and corned beef served club-style) or the Viva Chelsea! (fresh mozzarella, tomato and basil), at local institution Empire Bakery, then hit the trails. Taughannock Falls State Park is the flattest in the area for hiking. The park's namesake waterfall — the tallest single-drop waterfall east of the Rockies — dramatically plunges 215 feet down rocky cliffs and can be easily accessed via the 1.5-mile round-trip Gorge Trail. From downtown, you can hop on the iconic Cascadilla Gorge Trail (face masks required) and connect with the Cornell University campus. Stone trails and staircases originally constructed in the 1920s ascend over 400 feet, taking hikers 1.3 miles out and back through the gorge and past tiered waterfalls. Dinner at famed natural foods restaurant Moosewood is a bucket-list experience for foodies. Bon Appétit magazine named this pioneer of vegetarian cooking one of the 13 most influential restaurants of the 20th century. Even carnivores will appreciate dishes such as Thai cashew veggie curry and Campari and citrus olive oil cake. (Due to COVID-19, the restaurant currently offers only takeout and delivery.)

Where to stay: La Tourelle, a 54-room hotel nestled on 70 acres in Ithaca, has an excellent spa and a locavore-centric bistro (request a terrace seat for garden views). Firelight Camps, the hotel's on-site glamping experience, delivers a taste of nature without your having to rough it. Each of the 19 elevated, safari-style tents comes furnished with a bed and Moroccan carpets, with hot showers and flush toilets a short walk away in the bathhouse.

 Adirondack chairs for relaxing along the shoreline of Cayuga Lake, Aurora, New York

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Cayuga Lake

Day 4: Ithaca to Aurora (27 miles)

If it's a Saturday or Sunday, grab breakfast at the Ithaca Farmers Market, which directly accesses the Cayuga Waterfront Trail, a lovely stroll along the Cayuga inlet. On a weekday, stop by the Coal Yard Café for a grab-and-go bite (bagel and coffee) or a more substantive meal (cheddar grits bowl topped with a fried egg). To reach Aurora, drive north on NY-34B. Call ahead to winery hop on the water with Bianconi Tours. The 27-foot pontoon boat departs Aurora four times daily and currently accommodates six passengers to meet social distance guidelines. The 4 1/2-hour Wineries by Water tour cruises Cayuga Lake's western shore, stopping at three wineries, including the Thirsty Owl (try the Riesling). Due to COVID-19 safety measures, some wineries, such as Hosmer Estate, conduct tastings on the boat. For dinner, reserve a table on the lakefront patio of 1833 Kitchen & Bar for serious food in a casual setting. Dishes such as braised endive with pea puree and pickled asparagus and pan-roasted chicken with succotash showcase local purveyors, and the wine list highlights the best regional producers.

Where to stay: Pleasant Rowland, creator of the American Girl brand, owns the Inns of Aurora, a collection of five intimate inns (Zabriskie House is the newest and largest, with 11 rooms) set on the village's elm-lined Main Street. Group activities are currently suspended, but you can book private experiences such as cooking lessons and yoga sessions.

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