The 10 Most Picturesque Towns in New York State

Ithaca is arguably the best foodie escape in New York State. The long cited (possibly-correct, but as of yet unproven) stat is that Ithaca has more restaurants per capita than New York City. Some of Ithaca’s best restaurants are on the commons—try Just a Taste for tapas at a cozy wine bar. Outside the commons, you must head to Maxie’s Supper Club & Oyster Bar for cajun fare and seafood. For a landlocked town, their oysters are incredible, as is their gumbo. Ithaca is, of course, within the Finger Lakes wine region, but is only home to one winery: Six Mile Creek Vineyard. In addition to their wines—the Cab Franc and the Vignoles being particular favorites—they are distilling innovative grape-based spirits that are worth a try.

Where to stay: Argos Inn, the stately mansion off the commons that has been converted to a boutique hotel and cocktail bar.

On the North Fork of Long Island, Greenport is picturesque, right on the water, and, best of all, less of a scene than Montauk. The town is quite historic—the 1840 Schoolhouse Museum is always a fun stop for history buffs, and it is home to 12 beautiful art galleries that are worth exploring while poking around the local boutiques. The North Fork wine scene is well-established; book a tasting at Kontokosta Winery, a family-owned operation sitting right on the Long Island Sound. For dinner, reserve at The Frisky Oyster—their menu highlights seasonal ingredients, and changes daily.

Where to stay: The Menhaden, a relatively new boutique hotel with “North Fork’s only hotel roofdeck.”

Yes, Catskill is a town in its own right, rather than just the name of the surrounding mountainous region. There’s lovely shopping on Main Street (cute New York State towns really favor “Main Street” as an apt name for their central street). Village Common Mercantile sells all-natural apothecary wares made on the property, and Crossroads Brewing Company took over what was once the Daily Mail printing facility in 2017 to open their Catskill Taproom. History buffs can traverse the Hudson River Skywalk, which connects two key landmarks: Thomas Cole National Historic Site and Olana State Historic Site.

Where to stay: The Long Neck Inn, a sustainable inn on 200 acres in the Catskill Mountains.

Ellicottville exudes 19th-century charm largely thanks to the extraordinarily well-preserved homes and buildings, the majority of which are over 100 years old. To give you a sense of the picture-perfect streets of Ellicottville, we’ll say this: a Hallmark Christmas movie was legitimately filmed in this town. Ellicottville has also become a ski (and après-ski, for that matter) destination in the northeast, with two mountain resorts: Holiday Valley and Holimont. Even with a population of only 2,000, the downtown area is remarkably lively, with inviting shops, restaurants, and bars lining the main village drag.

Where to stay: The Jefferson Inn, a Victorian property from the 1800s.

The village of Aurora dates back to 1789 and sits right along Cayuga Lake. Strolling along Main Street—that’s right, Main Street again—in Aurora feels transporting in that it’s relative calm and quiet, scenic, and has good antique shopping. The culinary scene revolves primarily around the Inns of Aurora’s impressive food and wine programming. They have a new demonstration kitchen, Aurora Cooks!, where visitors can take workshops. Beyond that, the Village Market in Aurora sells delicious take-away meals made by the Inns of Aurora chefs. 

Where to stay: Inns of Aurora, on the shores of Cayuga Lake, and home to 1833 Kitchen & Bar.

Adirondack luxury awaits in Lake Placid, with high-end resorts and exceptional mountain views no matter the season. Leaf-peepers flock to Lake Placid in the fall, followed by the ski and snowboard crowd heading to the Whiteface Lodge in the winter. And in the summer, city dwellers come for a bed and breakfast weekend by the lake. Some of the best New York State hiking is in and around Lake Placid. Hike to Whiteface Landing or High Falls Gorge when the weather permits.

Where to stay: Whiteface Lodge—if the mountain views don’t sell you, the warm cookies and in-suite fireplaces will.

In the Hudson Valley, Rhinebeck has a darling town center with boutique shopping and a strong baked good presence at Bread Alone. For the local shopping, be sure to stop by Paper Trail and Rhinebeck Antique Emporium. For a town of fewer than 8,000 people, they host a remarkable number of festivities that visitors will enjoy, like the holiday Sinterklaas festival. Thanks to the Catskills backdrop, Rhinebeck feels like a European escape, despite being only two hours from NYC. The area is home to a number of historical sites, including Beekman Arms & Delmater Inn, the oldest inn in America, and the Home of Franklin D. Roosevelt in Hyde Park.

Where to stay: Mirbeau Inn & Spa, a boutique hotel that just opened this fall.

Livingston Manor is a charming Catskills town—so charming, in fact, that it inspired a bar in Downtown Brooklyn. Visitors can spend a full day just touring Livingston Manor’s breweries and distilleries—Prohibition Distillery USA, Roscoe Beer Company, and the Catskill Brewery. Between the mountains, the shops, and most importantly, the covered bridges, the town is a lovely sight to see.

Where to stay: The Arnold House on 80 acres of forest surrounding Shandelee Mountain.

About five hours north of New York in the Adirondacks, Saranac Lake is an outdoor recreation capital. A surprisingly small village with just 5,000 people, Saranac Lake is a town of water and mountain views with a growing food scene. They host a first night celebration to ring in the New Year and Saranac Lake Winter Carnival that runs for nearly two weeks, starting at the end of January. For an upscale dinner, try Red Fox Restaurant & Bar or rustic French fare at Left Bank Cafe.

Where to stay: Hotel Saranac, a recently renovated inn in the heart of the town.

Sag Harbor is somehow part of both Southampton and East Hampton, yet has retained a lot of its local charm rather than skewing commercial. The colonial-esque beach homes give off classic Americana flavor. Oh, and the town is famous for the reference Melville makes to Sag Harbor in Moby Dick. A town since 1846, set on the South Fork of Long Island, preservation is top-of-mind in Sag Harbor—many Sag Harbor landmarks make the National Register of Historic Places. Locals and visitors love to grab a table at Dock House on the water—their chowder is legendary—or buy lobsters and fish from the restaurant to grill, boil, or fry up at home. 

Where to stay: The American Hotel, built in 1846, the year Sag Harbor was founded.