Shops, eateries, and baseball-themed attractions line the sidewalk on Main Street in this charming upstate New York town. Image credit Kenneth Sponsler via Shutterstock.

12 of the Most Charming Towns in New York

The first visuals that come to mind whenever one thinks of holidaying in the Mid-Atlantic State of New York in the American Northeast are the incredible internationally acclaimed attractions of New York City. However, if one ventures out of the Big Apple to tour the rest of the State, their heart will surely be captivated by the countless spellbinding small towns that are a sharp contrast to the sparkling bright lights and roaring sounds of “The City That Never Sleeps.” From eccentric settlements at the base of majestic mountains to calm lakeside communities, the Empire State towns are excellent places to de-stress and fathom the region's pristine beauty. So, whenever you make arrangements for your next relaxing holiday in the Empire State, do not forget to add these lovable towns to your travel plans.

Saranac Lake

The beautiful small village of Saranac Lake, New York. Editorial credit: debra millet / Shutterstock.com
The beautiful small village of Saranac Lake, New York. Editorial credit: debra millet / Shutterstock.com

This teeny lakeside town and an all-weather vacation getaway, often called “The Capital of the Adirondacks,” spans the boundary betwixt Franklin and Essex counties within the confines of the Adirondack Park, around 9 miles west of Lake Placid. Saranac Lake, one of the most charming settlements of Upstate New York, boasts infinite cultural treasures and outdoor recreations. During summers, travelers can partake in fishing, canoeing, paddle-boarding, and boating activities at the 300-acre Lake Flower, while in cold seasons, a variety of activities like snowshoeing, snowmobiling, ice skating, cross-country, and downhill skiing are offered at the neighboring ski resorts. In addition, the Saranac Laboratory Museum, Adirondack Carousel, Saranac Lake Community Store, Robert Louis Stevenson Cottage & Museum, the myriad historic properties and art galleries, and musicals held at the different live performance venues attract thousands to Saranac Lake throughout the year.

Cooperstown

Main Street in charming Cooperstown, New York. Editorial credit: Kenneth Sponsler / Shutterstock.com
Main Street in charming Cooperstown, New York. Editorial credit: Kenneth Sponsler / Shutterstock.com

Otsego County’s seat, Cooperstown, sits on Otsego Lake’s southern edge in the Central New York Region, about 60 miles west of Albany and 145 miles northwest of New York City. Much of Cooperstown is encompassed by the 414-acre Cooperstown Historic District, having a total of 232 contributing properties such as the US Post Office-Cooperstown, Doubleday Field, Inn at Cooperstown, Iron Clad Building, Otesaga Resort Hotel, and many more. Annually, hundreds of baseball fanatics congregate at Cooperstown to take note of the huge number of baseball-related artifacts exhibited at the National Baseball Hall of Fame & Museum. Also, stop by the Fenimore Art Museum, Farmers’ Museum, and Clark Sports Center, besides enjoying world-class operas and Broadway musicals performed at the Glimmerglass Festival’s Alice Busch Opera Theater and partaking in recreational activities at the Glimmerglass State Park.

Lake Placid

Water boarder enjoys summer day on Mirror Lake in Lake Placid, New York. Image credit Leonard Zhukovsky via Shutterstock
Water boarder enjoys summer day on Mirror Lake in Lake Placid, New York. Image credit Leonard Zhukovsky via Shutterstock

Lake Placid, a lovely Essex County town, is located near its namesake lake’s southern periphery in the Adirondack Mountains, approximately 50 miles southwest of Plattsburgh. Well-known worldwide for hosting the 1932 and 1980 Olympic Winter Games, the town tempts adventurists with snow-covered mountains, untouched lakes, luxuriant green hills, and ski slopes. The abutting Whiteface Mountain allows Nordic and Alpine winter sports fanatics to participate in downhill skiing, mountain biking, ice climbing, hiking, gondola riding, and speed skating activities. The innumerable local shops, pubs, bakeries, and premier restaurants like Smoke Signals and Dancing Bears Restaurant make the town’s lovely Main Street apt for a winter stroll. Nevertheless, Lake Placid is not just an alpine paradise; the Lake Placid Lodge, Adirondack State Park, and Lake Placid Olympic Museum are some four-season tourist magnets.

Woodstock

The town center of Woodstock, New York. Image credit littlenySTOCK via Shutterstock.
The town center of Woodstock, New York. Image credit littlenySTOCK via Shutterstock.

Situated wholly within the limits of Catskill Park, this Ulster County town is at the foot of the southern Catskill Mountains, exactly 10 miles northwest of Kingston. Woodstock is admired all over the globe for being a year-round refuge and a distinguished artists’ colony that expanded after Ralph Radcliffe Whitehead set up the Byrdcliffe handicraft community north of the town. Sightseers at Woodstock must spend time on Tinker Street and check out the scores of shops, boutiques, local inns, eating establishments, the Tinker Street Cinema, Woodstock Public Library, and Woodstock Artists Association & Museum. Also, visit the Woodstock Playhouse, the Woodstock Festival Grounds in the proximate Bethel, the Bearsville Theater, and the nearby Karma Triyana Dharmachakra Tibetan Buddhist Monastery.

Aurora

The Pettibone House at Wells College campus in Aurora, New York, USA. Editorial credit: PQK / Shutterstock.com
The Pettibone House at Wells College campus in Aurora, New York, USA. Editorial credit: PQK / Shutterstock.com

“Aurora-on-Cayuga,” as the name says, is a stunning college town home to the reputable Wells College in Cayuga County alongside Cayuga Lake’s eastern banks, with only 607 residents per the latest US Census. The Aurora Village-Wells College Historic District encompasses more than 50 contributing buildings of various architectural styles and periods, including the Masonic Lodge, residential houses, commercial properties, barns, churches, and cemeteries. Furthermore, the Howland Stone Store Museum, Rowland House, Treleaven Winery, Fargo Bar & Grill, E.B. Morgan House, 1833 Kitchen & Bar, Village Market, Long Point State Park, and the Cayuga Wine Trail’s Long Point Winery are Aurora’s outstanding places of interest.

Rhinebeck

East Market Street in Rhinebeck, New York, via Ritu Manoj Jethani / Shutterstock.com
East Market Street in Rhinebeck, New York, via Ritu Manoj Jethani / Shutterstock.com

Rhinebeck, an alluring Hudson Valley town in the northwestern portion of Dutchess County, forms a part of both the Poughkeepsie-Newburgh-Middletown Metropolitan Area and the Greater New York Metropolitan Area. A cultural hotspot, Rhinebeck invites vacationers to discover the multiple stately homes, coffee shops, museums, specialty stores, entertainment spaces, and top-class restaurants such as Pizzeria Posto and The Tavern at Beekman Arms. Do not overlook the Old Rhinebeck Aerodrome, the Richard B. Fisher Center at Bard College, the Mirbeau Inn & Spa, and the Wilderstein Historic Site. Revelers must try to attend the Dutchess County Fair held in August at the Dutchess County Fairgrounds and the different activities and performances of children in the one-day Sinterklass Festival.

Greenport

Street view in Greenport, New York
Street view in Greenport, New York

Originally established as a ship-building and whaling mecca, Greenport is an adorable waterfront village on Long Island’s North Fork in Suffolk County. Presently, a preferred summer vacay spot for those holidaying in Long Island, the town enthralls tourists with the Greenport Village Historic District’s vast collection of unsullied 18th and 19th-century buildings. Lining Greenport’s serene streets are several locally-owned shops, ice cream parlors, boutiques, bars, bed & breakfasts, and finest eateries such as Sterlington Deli and Bruce’s Cheese Emporium & Café. When in town, the Railroad Museum of Long Island, Mitchell Park’s Camera Obscura and Antique Carousel, Cindy Pease Roe Artist Studio & Gallery, and Kontokosta Winery are must-visits, apart from attending the Maritime Festival organized by the East End Seaport Museum & Marine Foundation every September.

Saugerties

People walk past a home decor store in downtown Saugerties, New York, via James Kirkikis / Shutterstock.com
People walk past a home decor store in downtown Saugerties, New York, via James Kirkikis / Shutterstock.com

A quintessential Hudson Valley community, Saugerties is located on the Hudson River’s western shores at the mouth of Esopus Creek in the northeastern part of Ulster County. Saugerties’s quaint village center is acclaimed for its mom-and-pop shops, the luxurious Diamond Mills Hotel, antique stores, and eateries like Miss Lucy’s Kitchen, serving classic American comfort food. Hang out at the Opus 40 - a 6.5-acre environmental sculpture park created by American sculptor Harvey Fite, and spare time from your busy schedules to tour the 161-acre Esopus Bend Nature Preserve, Saugerties Lighthouse, Seamon Park, Catskill Animal Sanctuary, and Cantine Memorial Field. Yearly, Saugerties hosts the Farmers’ Market on Main Street, Saugerties Artists Studio Tour, concerts at Opus 40, ProMusica chamber-music series at Saugerties United Methodist Church, Mum Festival in Seamon Park, ShoutOut Saugerties, Hudson Valley Garlic Festival in Cantine Field, and Sawyer Motors Car Show.

Ellicottville

Ellicottville Town Hall in Ellicottville, New York. Image credit: Jimmy Emerson DVM via Flickr.com.
Ellicottville Town Hall in Ellicottville, New York. Image credit: Jimmy Emerson DVM via Flickr.com.

Ellicottville, christened in honor of Joseph Ellicott - an American surveyor, is situated in Cattaraugus County in Western New York’s north-central part. A namesake village in the southwestern portion of the town initially served as the county's administrative center. Although Ellicottville receives vacationers throughout the year, its population especially swells during the ski season, mostly due to its proximity to the Holiday Valley Ski Resort and HoliMont Ski Club. Moreover, travelers can window-shop from an array of shops, boutiques, and small businesses in Ellicottville’s central business district. Located close by at Parkside Drive, the 8-acre Nannen Arboretum & Botanical Garden allows nature lovers to relax in the tranquil settings.

Saratoga Springs

Exterior of a brick building in the historical center in Saratoga Springs, NY. Editorial credit: Enrico Della Pietra / Shutterstock.com
The exterior of a brick building is in the historical center of Saratoga Springs, NY. Editorial credit: Enrico Della Pietra / Shutterstock.com

Saratoga Springs, a scenic Saratoga County town, occupies the Hudson River Valley in the east-central part of New York. The Saratoga Race Course, the Frances Young Tang Teaching Museum & Art Gallery, the National Museum of Racing & Hall of Fame, Yaddo - the 400-acre artists’ community, Saratoga Springs History Museum, the Saratoga Performing Arts Center, and zillions of natural mineral springs scattered all over have made the community the most sought-after tourist retreat for centuries. History buffs must stop by the Saratoga National Historical Park, located 15 miles outside Downtown Saratoga, which, during the Revolutionary War, has been the site of the crucial Battles of Saratoga. Annually, the town hosts the Flurry Festival over the Presidents’ Day weekend, “First Night Saratoga” - New York’s biggest New Year’s Eve celebration outside the Big Apple, and the Saratoga Native American Festival in the fall season.

Watkins Glen

Visitors enjoy a picturesque view from the iconic Pier House at Watkins Glen.
Visitors enjoy a picturesque view from the iconic Pier House at Watkins Glen.

Schuyler County’s administrative center, this 1,829-inhabitant village, sits on the southern edge of Seneca Lake, approximately 20 miles north of Elmira. Primarily named “Jefferson” at the time of its incorporation, the settlement was rechristened in honor of the early promoter Dr. Samuel Watkins. The most noteworthy attraction of Watkins Glen is the 778-acre Watkins Glen State Park - the state’s flagship park featuring a 400-foot-deep limestone gorge cut by Glen Creek, which descends through the gorge, creating several rapids and waterfalls. From mid-May to early November, tourists can access the park’s Southern Rim Trail, Gorge Trail, and Indian Trail to climb or descend the gorge. Additionally, the town is widely known for being home to the 271-acre Watkins Glen Farm Sanctuary, the International Motor Racing Research Center, and the Watkins Glen International race track which has hosted the NASCAR Cup Series, Formula One United States Grand Prix, the IndyCar Series, and the IMSA SportsCar Championship races in the past years.

Skaneateles

Skaneateles, New York. Editorial credit: PQK / Shutterstock.com.
Skaneateles, New York. Editorial credit: PQK / Shutterstock.com.

Skaneateles, an opulent village in Onondaga County, is fittingly named after its placement at the northern limit of Skaneateles Lake on the Finger Lakes region’s eastern point. The village’s most discernible place of interest is the spotless Skaneateles Lake, called “The Roof Garden of the Lakes” due to its comparatively high altitude than other Finger Lakes. Browse the umpteen retail shops, boutiques, galleries, restaurants, real estate offices, and mid-19th to early 20th-century landmark properties lining the Genesse and Jordan Streets - the nucleus of the Skaneateles Historic District. Unwind at the Skaneateles Boutique Hotel and try to be present at any of Skaneateles’s annual events, such as the Skaneateles Antique & Classic Boat Show, Skaneateles Festival of Music, and Dickens Christmas in Skaneateles.

From Saranac Lake - “The Capital of the Adirondacks” to Saratoga Springs - “The Spa City,” these bewitching towns are waiting to be discovered by travelers in the nation's 27th largest and 4th most-populous state. With heavenly sceneries, unique downtown areas, intriguing histories, restaurants serving scrumptious cuisines, cheerful celebrations, and abundant recreations, the towns in the Empire State are a delightful escape away from the merciless pace of urban metropolises.

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