8 Playfully Peculiar Towns In New York
Synonymous with dominance, business, and glam, New York is unapologetically charming and exciting beyond when you break out from the swelter and herd mentality into the unexpected. From French heritage to castles, and doomingly, "The End," it is time to discover another side of the enigmatic Empire.
New York is an all-around alluring destination. Over 60% of the state is forested, and Adirondack Park is larger than any national park in the contiguous US. Between several beach towns and a few Halloween destinations, you are set to soak in every ounce of summertime sunshine or dive into foliage in these playfully peculiar towns in New York.
Cape Vincent
Once settled by the French in the 1,000 Islands region, Cape Vincent boasts colorful heritage and marine life. In the early 1800s, the lesser-famous Bonaparte brother, Joseph, established residence here for his infamous sibling, Napoleon. Never mind his efforts—the latter never committed to settling in Cape Vincent, seeking refuge elsewhere post-havoc in Europe. Lo and behold, the town celebrates its proud French roots during the French Festival around Bastille Day in France, a feverish weekend of French-themed fun on the second Saturday in July.
Visitors enjoy exploring local flora and fauna outdoors and indoors at the Cape Vincent Fisheries Station and Aquarium, bursting with underwater life. Cape Vincent Historical Museum delves into the War of 1812, rebuilt gloriously to match the deeds of local soldiers within an elegant stone building near a restored gristmill. To keep the excitement going, an auto ferry departs from Cape Vincent across the St. Lawrence River to the picturesque archipelago's largest Wolfe Island. The second leg is an unforgettable journey to Kingston, Canada.
Croton-on-Hudson
Under 50 miles from NYC, Croton-on-Hudson has magnetic charm at the confluence of the Croton and the Hudson rivers. Could it be the Croton Dam, hailed as the second-largest hand-hewn masonry? Croton Gorge Park is a 97-acre site at the base for fishing, hiking, and relaxation, with impressive views of the dam and spillway. The 508-acre Croton Point Park sprawls the riverfront with breathtaking views across the village, a boat launch, a campground, fishing, picnic areas, and a swimming area on the Croton River.
Settled by the Dutch, some residents have ties back to 1677. Amongst them, artists and musicians carried the legacy of their politically active predecessors into the progressive present. Boasting rare natural beauty, the peaceful river sounds and frequent breezes are heavenly on a hot summer day. Residents enjoy swimming and boating on the river, as it flows through beautiful hills and turning trees everywhere during fall. The Great Jack O’Lantern Blaze is a museum and site of thousands of intricately carved pumpkins lit up by night.
Hammond
Home to under 2,000, the Town of Hammond encompasses hamlets like Chippewa Bay along the St. Lawrence River across from Canada. It is both a jet-setter to Thousand Islands and fascinating to explore the secluded lifestyle on foot or kayak out from Schermerhorn Harbor. The Macsherry Trail buzzes with wildlife, while the Kring Point State Park juts into the bay on a peninsula with a beach, fishing docks, and scenic campsites. George Boldt explored the area in 1896, leaving his mark down offshore—the massive stone Boldt Castle.
Dark Island draws worldwide travelers with its imposing views of Singer Castle. Built from tons of granite quarried from nearby Oak Island, this 120-year-old, 28-room chateau features artifacts, beautiful furnishings, and puzzling passages on a tour. Away from the imposing Oak Island views, untouched trails traverse the aptly named Lonesome Bay State Forest, backed by Black Lake, and local restaurants for every taste. Meanwhile, the Iva Smith Memorial Gallery of Fine Art is a quirky museum, aka "The Yellow Barn."
Massapequa
Just 16 miles west of Islip, this village in the town of Oyster Bay is a true traveler's respite on the South Shore of Long Island. Dip your toes in the natural beauty of the bay along the hidden Philip B. Healey Beach at Florence Avenue, a kid-friendly playscape with a beloved ice cream truck. In addition to the nearby pier and Nickerson Beach Park, many enjoy the six-mile sand frontage at Jones Beach State Park plus its infamous outdoor theater arena. The neighboring Massapequa Park is renowned for food, drink, and entertainment.
The original Lenape tribe named the town, which translates as the “Great Waterland,” from the Algonquin language. Native American street names decorate Nassau County today, while Massapequa took a playful spin, naming streets after trees and places, including Jerusalem, Toronto, and New Hampshire avenues. The Nassau-Suffolk Greenbelt Trail starts between the thoroughfare and Massapequa Lake within the preserve. Taking the Bethpage Bikeway through the Massapequa Preserve, you can bike or run the 13-mile bikeway.
Montauk
There is no other place in the world like the playful Montauk, precariously dubbed as "The End." Tipping off the eastern edge of Long Island, this popular surfing destination is sometimes misjudged as kitsch or bougie. Ringed by pristine beaches, its reputation holds up as one of the state's best beach towns. The serene Ditch Plains Beach is ideal for swimming and surfing with unobscured views proximate to restaurants and lodgings. Visitors return time and time again for the captivating scenery that never gets boring.
The state's oldest lighthouse tips off the "island" within a dedicated state park with access to the top for breathtaking views. The 1796 Montauk Point Lighthouse Museum was authorized under President George Washington. In addition to the museum, the adjacent park is great for eyeing the landmark from the picnic area, surf fishing, and nature trails against the stunning Atlantic at sunset. In lieu of hotels and expensive Airbnbs, Hither Hills State Park offers a recreation area along the dunes with a large campground.
Roscoe
Just within the boundary of Catskill Park, Roscoe is known for its unique nature, trout infatuation, and the local “Catskill Style Dry Fly” technique. Though named after a former state senator, “Trout Town USA” is near five of the nation's top trout streams at the Beaverkill River and Willowemoc Creek crossroads. The quirky Junction Pool is a "loitering area" for the fish trying to decide which stream to swim up, where Theodore Gordon, a writer, fished and wrote about. Meanwhile, Roscoe Campsite Park offers cool sleeper wagons and alpacas on site.
Wildlife trails traverse forested landscapes and sites along the way, including the neo-Gothic Dundas Castle, also called Craig-e-Clair. Surrounded by lakes and reservoirs, Roscoe boasts ideal geography for anglers, kayaking, and plain nature enthusiasts on a refreshing hike to Russell Brook Falls, and tasty fish waiting for them in the town's restaurants. Get this: while others reel for brook, brown, and rainbow trout, you can taste your own "grand slam." In fact, Roscoe celebrates the trout season opening over "Two-Headed Trout Dinner."
Sleepy Hollow
How did a sweet name become central to one of America's horror tales? Settled by the Dutch in 1640 as part of North Tarrytown, Sleepy Hollow was named and emerged as an independent village only in 1996. Known officially from the 1820 short story by Washington Irving about Ichabod Crane's encounter with the Headless Horseman, the literary giant lived in Tarrytown and based his story on the local area. Sleepy Hollow brings the story alive through iconic sites, like the Sleepy Hollow Cemetery and the nearby Pocantico River.
The Croton Aqueduct Trailway leads past a stone 17th-century Old Dutch Church, gorgeous in its simplicity. The great author was buried at the cemetery behind, among the area's earliest Dutchmen, whose gravestones date back to the 1600s. The riverfront greenway is a beautiful place year-round to see the iconic 1883 lighthouse and cross the new bridge, which replaced the old Tappan Zee Bridge. Catch the moody Hudson River views across the 3.6-mile shared pedestrian and cyclist path, plus art displays, when you visit during Halloween events every weekend in October.
Ticonderoga
This beautiful town at the head of the long Lake George, across Lake Champlain from Vermont, draws nature lovers, history fanatics, and sci-fi fans. The Falls of the La Chute spill right in downtown Bicentennial Park on the La Chute River, which flows into the lake. It is refreshing on a hot summer day, ideal for pictures, shore fishing, and a covered bridge along a nature path with placards on the fall-powered mills. From downtown, take a hike or drive up Defiance Mountain to savor the historical landscape alongside a picnic pavilion a short, steep walk away.
At the focal point, the internationally known 18th-century Fort Ticonderoga was active during two wars. The strategic location played a pivotal role during the Revolutionary War, with a unique star-shaped design and attractions that bridge history. Today, the 2,000-acre area offers interactive exhibits, engaging demonstrations, gardens, and a weapons collection. King's Garden is beautifully maintained to reflect various historical periods. Meanwhile, the town's Star Trek Original Series Set Tour reveals authentic sets from the iconic 1966 to 1968 television series.
Home to playful and downright peculiar towns, the Empire is a playscape of curiosities and adventures. Whatever business brings you to New York, it transforms you in the whispers along the forest trails, the swooshing foliage, and the chirping birds.
From epic pumpkin displays and cemeteries to trout dinners and sci-fi, these eight let their playfulness out to varying degrees of peculiarity. Find yourself amidst peaceful river sounds and frequent breezes along the Hudson in your backyard. Hereon, no getaway shall be anything less than extraordinary.
