9 Most Picturesque Small Towns In New York
The camera loves New York. Not only does each borough of the namesake city offer something stimulating, but once you clear the Big Apple, it becomes evident how much wilderness actually awaits. Some may find it surprising that The Empire State has one of the highest percentages of forest coverage in the United States. Add in the Adirondack, Catskill, and Appalachian Mountains, the Finger Lakes region, the Hudson Valley, and Long Island's coastlines, and New York easily becomes one of the most picturesque parts of the county. But another appealing aspect of this multitudinous state that should not be overlooked is its cache of attractive small towns. These nine gems build on New York's natural beauty with their colorful and creative personalities.
Lake Placid
This energetic village in the Adirondack Mountains is not only a two-time host of the Winter Olympics and an all-around sports mecca but is downright gorgeous from all angles. Lake Placid is ideally situated on the southern shores of the eponymous lake and also surrounds the much smaller Mirror Lake. Bountiful green forests border the bold, blue bodies and stretch off as far as the eye can see into the rolling landscape of both the 36,200-acre McKenzie Mountain Wilderness and the 23,000-acre Sentinel Range Wilderness. With that said, there's no need to flee the village to embrace nature.
There is a network of peninsula trails that begins on the north side of town and several other wooded hikes that kick off mere minutes to the west. But you may not even make it that far, for once you lay eyes on Lake Placid's infectious Main Street, an afternoon of window shopping and trying to settle on a scenic restaurant could easily slip away (in a good way).
Sleepy Hollow
Sleepy Hollow is another New York village with a split personality. It is most commonly known as the setting of Washington Irving's short story, The Legend of Sleepy Hollow, but don't let the gripping tale of the headless horseman overshadow how picturesque and inviting this place really is. Sleepy Hollow rests on the eastern shore of the Hudson River, just north of the impressive Governor Mario M Cuomo Bridge. Cruise the Scenic Hudson Riverwalk, beginning in Pierson Park, until you reach the cute, rustic lighthouse from the 1880s and adjacent community mural.
Then, head inland to see the various stately churches, Kyuit (the 40-room Rockefeller estate, gardens, and art collection), and the expansive Rockefeller State Park Preserve. Sleepy Hollow's aesthetic transforms throughout the seasons, making it a true year-round getaway for anyone in the Big Apple (only 40 minutes by train from Grand Central).
Watkins Glen
Watkins Glen is not only one of the most picturesque small towns in the state of New York, but it is one of the most overlooked towns in the Northern United States. This Schuyler County village sits at the southern end of Seneca Lake – one of the many slender and scenic bodies of water in the famous Finger Lakes region. Start with a boardwalk stroll out to the photogenic, red-shingled pier house. Next, clear some space on your phone/camera for the plethora of waterfalls in the immediate vicinity.
The Gorge Trail in Watkin Glens State Park (a serene extension of the town's western half) passes by no less than 19 of them while navigating the rocky, moss-covered cliffs. For a panoramic view of the area, hike to the old fire tower lookout in Sugar Hill State Forest (also just west of Watkins Glen), or delve deeper into the tranquil woods by exploring Finger Lakes National Forest (to the east).
New Paltz
Plunked beside the Wallkill River (a few miles west of the Hudson) and sheltered beneath the jaw-dropping Shawangunk Ridge, this Ulster County town is painted with many different colors. For starters, New Paltz was settled by French Huguenots in the early 18th century. Seven original stone houses (and one church that was faithfully reconstructed to its 1717 state) can be seen along Historic Huguenot Street – a National Historic Landmark District.
Keep the old-fashioned flavor going with a trip into Mohonk Preserve (just west of town), where 70 miles of carriage roads and hiking/biking/horseback riding trails cover the northern Sawangunk Ridge. And for a truly breathtaking sight, continue west into Minnewaska State Park Preserve to marvel at the Mohonk Mountain House – a world-famous resort at the northern tip of the small but dramatic Mohonk Lake.
Kingston
Let's continue following the Hudson River northbound, this time to the underrated small city of Kingston. This seat of Ulster County was once the capital of New York. Nowadays, it is the history and scenery that makes Kingston shine. The Stockade District (i.e. historic district) is composed of eight blocks of 17th-century structures that are designated National Historic Places and Landmarks, as well as quirky local businesses, such as Sissy's Cafe and Rough Draft Bar & Books.
Over on the waterfront, Kingston sports the Hudson River Maritime Museum (complete with a rotating exhibit of antique ships anchored in the river), a sandy public beach, and the Rondout Lighthouse, which can be seen atop its lonely island platform from Kingston Point Park.
Saugerties
Another twelve miles or so up the west bank of the Hudson, the quiet town of Saugerties emerges. Like Kingston, one of the most photographed features of this riverside community is its lighthouse. Established in 1869 at the intersection with Esopus Creek, this weathered, red-brick creation now operates as a two-room, high-end Bed & Breakfast. But whether or not you choose to shell out for a night (the going rate is $550 for up to four people), the charming facade and short surrounding trails of Ruth Reynolds Glunt Nature Preserve are well worth the meander out of downtown.
Saugerties is blessed with a quintessential small-town commercial district, which sprawls across the highly walkable Main and Partition Streets.
Woodstock
Occupying the western apex of the geographical triangle with Kingston and Saugerties is the ever-colourful and invigorating town of Woodstock. This hippie haven preserves the spirit of the Juggernaut 1969 festival, promotes local artists and small businesses, and is a gateway to endless adventures in the Catskill Mountains. Follow the three main arteries, Tinker Street, Rock City Road, and Mill Hill Road, for a snapshot of the eclectic community.
First-time visitors will be delighted by the numerous performing arts centers, galleries, and museums. Woodstock is also replete with vintage clothing shops, crafty boutiques, and health-conscious eateries. Basically, if it is inspiring for the body, mind, and/or soul, then you'll probably find it here. Heck, Woodstock even has a Tibetan Buddhist monastery and the world's largest kaleidoscope.
Montauk
New Yorkers love to retreat up the Hudson, but they also flock out to Long Island to appreciate the splendor of the Atlantic and Long Island/Block Island Sound. Montauk, the easternmost community, is known for its many romantic beaches and pristine coastal parks (of which there are 5,000 combined acres), boating, paddling, and fishing opportunities, luxury accommodations, and fine dining. At the risk of overselling New York's lighthouses, I can't help but point out the Montauk Point Lighthouse. Erected in 1796, this 111-foot icon is the oldest such beacon in the state and fourth-oldest in the country.
From this easternmost extent of the island's south fork, one has a clear view of the choppy ocean waters and the coast of Connecticut, as well as access to the adjacent museum.
Skaneateles
Skipping back to Finger Lakes, the hamlet of Skaneateles is one of the prettiest in the region. Perched at the top of the dazzling-blue, 16-mile-long Skaneateles Lake (which, by the way, is the cleanest of all its peers and one of the cleanest in the country), this Onondaga County community is always ready to welcome tourists. The tranquil Clift Park waterfront transitions into the lengthy Skaneateles Pier, which affords excellent views of the lake and the inviting village that awaits on the east side of the creek.
Genesee Street (in conjunction with Jordan Street and the Old Stone Mill) marks the Skaneateles Historic District, which has been listed on the National Register of Historic Places due to its wealth of well-preserved 19th-century buildings. Modern-day visitors will appreciate the timeless atmosphere and the lively retail and restaurant scene that it now supports.
These nine small towns show off the many sides of New York's beauty. The Empire State harbors lakes great and small, multiple tree-covered mountain ranges, ostentatious river valleys, and a tease of the Atlantic coastline. However, these cool communities also show off the cultural side of New York: its early colonial and maritime history, its flair for the arts, and its independent spirit that promotes towns with individual characters. So don't just beeline for the Big Apple; check out some of what Upstate New York or Long Island offers. Your inner photographer will thank you.
