9 Fairy-Tale Small Towns In New York
New York keeps its storybook towns up in the mountains and out along the water. Lake Placid makes the case first below the state's tallest peak. The Adirondack village has hosted the Winter Olympics twice. The Finger Lakes carry the theme west with vineyards planted above glacial water. Montauk pushes it east to surf breaks and open Atlantic light. The enchantment here rests on real history and real landscape. These nine towns earn the fairy-tale label the honest way.
Lake Placid
Lake Placid may be best known for hosting the 1932 and 1980 Winter Olympics, yet this North Country town also makes for a great escape before the snow starts to fall. Summer and fall are good times to head into the High Peaks Wilderness Area. Hikers can climb New York's highest summit at Mount Marcy, which rises 5,343 feet above sea level. The 275,460-acre preserve holds many more of the Adirondack 46 High Peaks. Nearby McKenzie Mountain Wilderness protects another 36,200 acres and a 3,822-foot summit. Visitors can also fish, paddle, and boat at Lake Placid and Moose Pond. And for a lovely day at the greens, folks can book a tee time at Lake Placid Golf Club and play up to 45 holes of scenic, award-winning golf at the region's only 45-hole golf course complex.
For the ultimate fairy tale-like experience at Lake Placid, it's hard to beat Whiteface Lodge. Inspired by the Gilded Age era hotels and vacation homes that once anchored the region, Whiteface Lodge combines classic elegant touches like handcrafted furniture and cast-iron fireplaces with contemporary amenities like flat-panel TVs and jacuzzi-jetted bathtubs. While here, guests can also indulge in sumptuous dining at their restaurants, and in soothing treatments at their spa.
Sackets Harbor
Out by the eastern edge of Lake Ontario, Sackets Harbor is home to some fascinating wartime history, and it's a present-day destination for peaceful lakeside splendor. In town, Sackets Harbor Battlefield State Historic Site marks the place of two battles during the War of 1812, with the second (in May 1813) resulting in U.S. forces fending off a robust attempt at a British-Canadian land invasion. A few blocks away, Fort Pike Park originally housed a military structure built during the War of 1812 to defend U.S. naval assets, but it's now a go-to spot for scenic walks and hikes by the lake. Westcott Beach State Park sits a short drive south. Its wooded bluffs draw hikers, and the sandy beach below is good for swimming and sunbathing. Boat launches let visitors set off across the water.
Back in town, the Harbor House Inn provides a convenient location near the harbor and the historic battlefield, and it's a comfortable haven to relax with extra plush bedding, fast wifi internet, and DirectTV premium channels.
Skaneateles
Just 20 miles east of Syracuse, Skaneateles opens up to the serene environment of the Finger Lakes region. In the central village, Clift Park has a community dock and a gorgeous swimming beach at shore, along with a lush garden area on dry land. For a wilder day in nature, visitors can head south to Bahar Nature Preserve and explore this 53-acre site with a hardwood and hemlock "hidden forest" and the 90-foot waterfall at Carpenter Falls. On the way back to town, they can also stop at Anyela's Vineyard to try their wide selection of New York-made wines, feast on their tasty pizzas and charcuterie boards, and maybe catch a weekend concert.
To cap off a Skaneateles getaway, it's worth checking into the Mirbeau Inn & Spa Skaneateles. The Forbes four-star resort evokes the elegance of a French chateau, and it features country chic rooms and suites, fine French-American fare at The Bistro & Wine Bar restaurant, and the full-service Spa Mirbeau.
Penn Yan
Travelers who want to try another side of the Finger Lakes will find one worth savoring at Penn Yan, a town at the north end of Keuka Lake. Anyone wanting a convenient one-stop shop for locally-made wines can go to Once Finger Lakes and sample some 40 Finger Lakes wines, 12 craft beers and ciders on tap, and a curated selection of local craft spirits. Meanwhile, more adventurous wineaus can venture out (with a designated driver) to Keuka Spring Vineyards for award-winning Rieslings, Bruscos, and Gewürztraminers, and to Vineyard View Winery for sustainable, handcrafted, boutique wines in a relaxing setting.
Near the heart of town, Trimmer House Bed & Breakfast makes a cozy and heartwarming place to stay. Set in a vintage 1890s Victorian house, the inn offers guest quarters chock full of antique furnishings alongside a full homemade breakfast every morning.
Mount Morris
Just 39 miles southwest of Rochester, Mount Morris sits at the foot of a landmark often called the "Grand Canyon of the East." The 14,350-acre Letchworth State Park protects a gorge carved by the Genesee River. The canyon reaches 600 feet deep in places, and 66 miles of trails run along it. A little way downstream, Indian Fort Nature Preserve is a good spot for hiking, wildlife watching, fishing, and paddling. Then, for a more genteel experience in town, Wendy's Pantry & Country Mouse Tea House has a lovely tea room to sit and enjoy a cup of tea, along with a store fully stocked with locally and regionally sourced specialty foods and gift items.
Staying in town, Allegiance Bed & Breakfast occupies a fully-restored historic (c. 1838) Federalist Revival mansion, and guests can expect accommodations with sweet amenities like Roku-ready flat-screen TVs, USB charging stations, individual air conditioning controls, and Beekman 1802 and Nest bath products.
Salamanca
Perched on the banks of the Allegheny River is Salamanca, the only United States town that's located entirely within Native American territory. Travelers can head to the Onöhsagwë:de' Cultural Center (formerly known as the Seneca-Iroquois National Museum) to learn about the area's indigenous heritage, tour their historic exhibits, and view their vast collection of beadwork, basketry, and antler carving art. For some more fascinating finds, Salamanca Mall Antiques operates one of the nation's largest antique retail spaces with over 1,000 individual vendors inside. Just to the south of town, Allegany State Park extends across 64,800 acres of Allegheny Highlands forest down to the Pennsylvania state line. It draws visitors year-round for hiking, camping, and warm-weather boating.
Returning to town, Seneca Allegany Resort & Casino serves as the region's hotspot for fine hospitality and hot entertainment. The AAA Four Diamond resort has a casino floor fully equipped with slots and table games, along with a regular lineup of live music acts, a wide array of restaurants, a full-service spa and salon, and 413 sleek and stylish rooms and suites.
Woodstock
Woodstock might not seem like a traditional fairy tale-like town, but there's something truly magical about this longtime epicenter of countercultural cool. From here, travelers can drive out to the Bethel Woods Center for the Arts to walk the hallowed grounds of the Woodstock Festival, tour the on-site museum, and even attend some present-day music concerts. Or, folks can stay in town and check out the Colony for intimate live music performances. And at Woodstock Artists Association & Museum, people can see paintings, sculptures, prints, and other visual works by local artists.
Close to Woodstock's main village, The Herwood Inn provides a quirky yet comfy "home away from home." Guests can pick from apartment-style rooms with Casper mattresses, sleeper sofas, kitchenettes, and HEPA air purifiers. The property also includes the Commune + Shop and the Shed Outdoor Oasis.
Cutchogue
Upstate regions like the Finger Lakes may have gained a reputation for great wines, but there's another New York wine country region that's just as worthy of a visit, and the town at the heart of it is only 97 miles east of New York City. Yes, really, Cutchogue sits in the middle of Long Island's North Fork wine country, and Borghese Vineyard & Winery is the "founding vineyard" that began making high-quality wines on Long Island some 27 years ago. In addition, folks can try the sustainably-grown red, white, and rosé wines of the family-run Sannino Vineyard. And at Pellegrini Vineyards, visitors can stop in the tasting room and enjoy their fine Old World-style wines.
For some more North Fork hospitality, guests can check into The Farmhouse Bed and Breakfast, kick back in their plush country home-style suites, and enjoy a hearty farmhouse breakfast made with locally sourced ingredients (including some from their own gardens!) every morning.
Montauk
Out at the easternmost point of Long Island, roughly 123 miles east of New York City, is a spectacular beach town called Montauk that marks "The End" of the Hamptons and the beginning of so many possibilities. Camp Hero State Park stretches across 415 acres of prime coastal woodlands and Atlantic Ocean facing beaches, including the Turtle Cove beach that's a favorite among surfers. Ditch Plains is another great local beach for surfing, and for more casual swimming during the summer season. On the west end of town, Hither Hills State Park covers 1,755 acres and a 189-site campground. The park holds the "walking dunes" of Napeague Harbor and a network of hike and bike trails. A long stretch of beach is open for swimming, paddleboarding, and windsurfing.
Just up the road from Hither Hills, Gurney's Montauk Resort & Seawater Spa marks the Hamptons' only year-round, full-service oceanfront resort, and guests are treated to a 2,000 foot-long beach that's reserved just for their use. Even better, guests can also make good use of Gurney's 30,000 square-foot Seawater Spa & BathHouse complex, multiple delectable restaurants, and seasonal activities like DJ beach parties and outdoor fitness classes.
Make Your Fairy Tales Come True While Visiting These Lovely New York Towns
What links these nine towns is range packed into one state. The Adirondack summits above Lake Placid and the open Atlantic surf at Montauk sit within a day's drive of each other. Sackets Harbor keeps its War of 1812 ground intact, while Salamanca remains the only U.S. town set entirely within Native American territory. The wineries around Penn Yan and Cutchogue reward a slow afternoon, and Woodstock still trades on its 1960s arts scene. A fairy-tale weekend here can mean a mountain trail, a battlefield, a tasting room, or a beach.
