The Best Small Towns in New York to Chill Out In 2024
Ah, New York, New York—but what happens when you want to venture outside the Big Apple? From the valley to Long Island, there’s an idyllic town within the crevices of the beautiful, rural landscape along the winding roads through rolling fields. Walk in the footsteps of the school teacher Ichabod Crane, the Headless Horseman, and the author of the short story himself in Sleepy Hollow through the refreshing Hudson Valley, which wraps around the Hudson River.
Established amid blissful geography in 1682 on the northern tip of Long Island, Greenport offers striking sunsets and the historic Horton Point Lighthouse Nautical Museum, as well as the wondrous Lavender by the Bay, with a rich selection of wineries, to chill with a glass in a fragrant purple bloom. Home to two rivers, a number of beaches, and the significant Croton Dam, visitors can enjoy top views of the town over a lush summertime picnic or cross-country skiing in winter.
Croton-on-Hudson
Drawing scores with many "only here" attractions, the New Croton Dam is historically and structurally significant for this town on the mighty Hudson River. Being the local lifeline as a water supply, the dam also symbolizes a revitalizing escape from the city for tourists, while the Croton River on its right flank multiplies the opportunity for aquababies, including nature trails and beaches like Lake Park and Croton Beach. Visitors can enjoy picnics high above or explore the area on a pair of skis in the winter. Aside from the number one attraction, the placid 1,500-plus-acre Blue Mountain Park tempts hiking enthusiasts with a refreshing breath of the wild, just 10 minutes north, via trails like the Summit Trail or the Reservation Loop, as well as scenic ponds for fishing.
Croton-on-Hudson, an all-around eclectic town in New York, keeps a real chill in the atmosphere. Stop by the 3rd Universe Comic Emporium or aspire to a seaside vibe at the hip Ocean House Oyster Bar & Grill. Beyond a fun downtown area lies rugged backcountry, like Croton Gorge Park, for energetic hiking and biking. After the leaves blaze up the trails in foliage, the Great Jack O’Lantern Blaze invites visitors under illumination from 7,000 hand-carved jack-o’-lanterns. Don't miss Croton Tapsmith to wrap up an ambient evening in good company. From a popular campground to a miniature airport for model plane enthusiasts, the peninsular 508-acre Croton Point Park offers a chance to chill out on a beach or enjoy nature trails and then relax in one of the spacious pavilions over a summertime BBQ.
Greenport
Perched on the northern tip of Long Island, Greenport is one of the most popular and convenient coastal escapes from NYC for all seafaring fans and romantics. From striking sunsets to seaside walks and lovely open-ocean vistas, don’t miss the East End Seaport Museum and the over-a-century-old carousel. Minutes west, the circa-1857 Horton Point Lighthouse Nautical Museum offers views of Long Island Sound and Connecticut, a beach, and a museum behind its long story. Home to some of the softest sandy beaches in the state, explore Pipes Cove in a kayak, lounge oceanfront along the Town Bridge, or enjoy the serenity on a boat ride along the pretty Hashamomuk Pond with a lush western bank; the beach overlooks the scenic Whale Rock. Others seek out the wondrous Lavender by the Bay, with a rich selection of wineries, to chill with a glass in a fragrant purple bloom.
Established amid blissful geography in 1682, the historic town exudes charm and a relaxed atmosphere that is a welcome respite from the city. Browse eclectic galleries between quaint shops and enjoy vineyard tours that pair well with fresh local cuisine. American Beech is a fun spot for lunch or dinner and is also a small but lovely hotel, while Brix & Rye and Greenport Harbor Brewing Company will mix up a perfect cocktail or pour you quality craft beer. Whether you’re in for sailing or antiques from the past, this historic town is an idyllic wine country retreat for every taste. Contrasting the bougie mansions in the nearby Hamptons, Southold Fish Market is a simple "must" for seafood lovers, while couples and adventurers may be interested in chilling out in solid serenity on Shelter Island after a breezy ferry ride.
Hunter
Hunter, a true Greene County mountain gem, offers a cozy atmosphere to relax amid the region’s highest peaks. Notably comprising two villages, Hunter and Tannersville, it is home to some of the Great Northern Catskills' greatest attractions, like Catskill Park, a true adventurer's paradise. In the warmer months, hikers can enjoy a variety of trails suitable for all skill levels, while families visit the kid-friendly resort, Hunter Mountain. Enjoy views from high above via a scenic sky ride to the 3,200-foot summit in any season at one of the Empire State's best skiing destinations, with the chillest vibes along its premier skiing slopes. Visitors can enjoy a long weekend getaway of skiing and snowboarding, from beginner to advanced, interspersed with other cold-weather activities like snow tubing.
Flowing from the mountain tops, the crisp Schoharie Creek runs through the heart of the town. Take a leisurely stroll waterside, with a great après-ski scene, a cozy cinema, and cute cafes. Whether you're drawn to the scenery or the wilderness, don't miss the resort's scenic Rip Van Winkle Stone Carving. With tourism in its blood ever since its settlement in the early 1800s, the Town of Hunter's resplendent geography for adventures and photography has long attracted city escapees to reach for their own alluring heights. Inspired by the outdoors and the freshest air, many artists, poets, writers, and wealthy travelers spread the word, establishing a creative community. Rust Diamonds & More is an antique store, while the antiquated Scribner’s Catskill Lodge, with a dash of 21st-century rustic cool, blends seamlessly into the surrounding high country as a highly sought-after place to rest near the resort.
Lake George
As long as "George" can remember, he has been a favorite NYC summertime escape for watersports, otherwise known as "The Queen of American Lakes." It is still a favorite Adirondacks town for those who enjoy a lively atmosphere—named the sixth-best "Place to Visit in New York State in 2024." From a historic steamboat cruise—a unique way to chase fall foliage—to a plethora of hiking nature trails, the sparkling waters reflect lakeside cabins and resorts. Visitors can capture the saturated summertime nature along the most popular yet arduous Prospect Mountain Hiking Trail for breathtaking vistas from the summit. Enjoy lounging on a beach or in a boat with panoramic views before the reds, oranges, and yellows set the lake on fire, framing it in a picture-perfect shot.
Home to the circa-1755 Fort William Henry, a legendary British fort featured in "The Last of the Mohicans," history buffs can dive into the French and Indian War at the Fort William Henry Museum. Lake George is also a gateway to Fort Ticonderoga just south along the long lake, while families appreciate the region's countless amusement parks. Home to scenic mini-golf courses and Splashwater Kingdom, the largest amusement park in the Empire State, Shepard Park is central, with a beach, playground, and amphitheater for summer concerts. Beyond swimming in the crystal-clear waters at Million Dollar Beach and other aquatic activities like parasailing, whitewater rafting, water skiing, and kayaking, don't miss the fun House of Frankenstein Wax Museum.
Ocean Beach
This glorious seaside village, the unofficial capital of Fire Island, offers a unique pace of life "on island time." Just a half-mile wide, it is easy to explore the treasure-laden 32-mile-long barrier beach island for all ages and interests. Luring travelers with its characterful boutiques, shops, and home-spun galleries, it inspires you to embrace individuality and feel at ease by the ocean. There's also the Seaview Market and a tasteful restaurant for every discerning palate. Combining the allure of a resort, locality, and the vestigial past that many other towns have left behind, Ocean Beach is particularly chill in the fall through spring. Springing into motion during the summer, visitors can enjoy nightlife by the beach, movies, art shows, sports courts, and a popular international film festival. Sailors Haven features a boardwalk to the sands, a marina, picnic facilities, and concessions, while Sunken Forest Preserve nails natural serenity.
Accessible via ferry and water taxi service or a seasonal and transient boat marina, you can enjoy sightseeing and people-watching along the beautiful, safe ocean and bay beaches, cute homes, and most of the island's hotels and B&Bs. Smack in the heart of Fire Island, Ocean Beach offers great access to it all, like the Ho-Hum Beach Marina in the west and, to the east, the historic Fire Island Lighthouse from 1858, with a charming keeper's house, nature trails, and scenic views from the sandy beach. From dockside concert performances to the three s's by the wave-crested Atlantic Ocean to the serene Great South Bay, rent a little red wagon or a bike and enjoy traffic-free summers. Nearby, the Fire Island National Seashore attracts bird-watchers and campers, while Robert Moses State Park at the western edge is a fantastic place to explore, chill, and sunbathe along one of the beautiful beaches, including swimming or surfing.
Sag Harbor
What makes Sag Harbor stand out among the other Hamptons is its seaside ambience coupled with an authentic feel. This humble and historic Main Street-incorporated village is a fun and easy escape back in time from both New York and Boston. Whether you're coming for shopping or to relax, cultural enrichment follows with landmarks, parks, and a side of seafood indulgences. Don't miss the unique Jayson Home and the old-timey cinema, while the Sag Harbor Whaling & Historical Museum dives into the significant whaling port of the 18th and 19th centuries. Visitors can unwind at the waterfront marinas until sunset, catch it from Circle Beach, and cap off the night at Dockside Bar & Grill.
Bay Street Theater is an absolute must-experience, offering concerts, workshops, or one of the regular masterclasses, with entertaining summer camps for kids while the parents relax. For nature lovers and photographers, the 187-acre Elizabeth Alexandra Morton National Wildlife Refuge features wildlife trails with white-tailed deer, turkeys, songbirds, and turtles. The 1.2-mile-long Wild Birds Nature Trail winds through wooded areas and the beach, stretching onto Jessup’s Neck Peninsula. Families enjoy the calm waters lapping up Havens Beach, while the popular Windmill Beach is mere steps from Main Street, and the mile-long Foster Memorial Beach is a serene option for couples.
Sleepy Hollow
Attracting literary fans from all over, this tiny town is the star in Washington Irving’s 1820 tale “The Legend of Sleepy Hollow.” Celebrating its anniversary this September, it invites visitors to join the rollicking block party as part of the yearlong festivities. Incorporated as North Tarrytown a century and a half ago, the charming village of Sleepy Hollow can be a relaxing escape any time of year from NYC into the bucolic charm of the Hudson Valley. Just 20 miles outside of the Big Apple, visitors can follow in the footsteps of the schoolmaster Ichabod Crane through the rich nature and fresh air and the hoofmarks of the infamous Headless Horseman, who notoriously galloped through the valley, full of historic landmarks like the Old Dutch Church, where Ichabod mysteriously vanished.
Sleepy Hollow Cemetery, one of the best places for strolls, is the final resting place of the author, a vestryman, Sunday school teacher, and regular parishioner, as marked by his pew at nearby Tarrytown’s Christ Episcopal Church on a brass plaque. Walk around the tombstones of former local residents who allegedly inspired other main characters, like Katrina Van Tassel, the female protagonist. Just south, the 18-foot-tall Headless Horseman statue offers serene views to digest the atmosphere and information over a picnic, with the church steeple just to the north. The schoolmaster took dates for a walk to the restored 17th-century Philipsburg Manor, a former milling and trading complex where enslaved Africans worked on-site, with upcoming tours in December.
The Empire State is a whole other world of chill-worthy nature and friendly small towns, as close as 20 miles from NYC. Sag Harbor, a significant whaling port in the past and an ambient seaside Hamptons town today, features a number of beaches, wildlife trails, and marina sunsets. From the waterfalls to the beaches and vineyards to award-winning restaurants and world-class wines, New York is a create-your-own adventure state.
So the question stands: how do you want to chill out in 2024? Ocean Beach on Fire Island inspires you to embrace individuality through its characterful boutiques and local galleries. Perhaps hiking in Hunter or Lake George, the king of water sports in the Adirondacks, and then back to the Catskills in winter along Hunter Mountain, a premier skiing destination, with a scenic sky ride to chill at 3,200 feet in any season?
