10 Cutest Small Towns In New York To Visit In 2024 (2024)

10 Cutest Small Towns In New York To Visit In 2024 (1)

Between man-made beauties like The Empire State Building and natural wonders like Niagra Falls, New York is a hot spot for tourists from around the globe. But a trip to the Empire State doesn’t mean you have to go to these highly-visited sites. There is just as much to enjoy (and fewer crowds) in some of New York’s smaller towns. From the waterfalls in Ithaca to the Halloween celebrations in Sleepy Hollow, there is a little something for everyone to enjoy here. So, if New York is on your 2024 travel bucket list, consider checking out one of these ten cute small towns instead.

More in New YorkThese 10 towns in New York have beautiful architecture.


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Welcome to the land of waterfalls. Ithaca, New York, is a gorgeous small town located right at the tip of Cayuga Lake. With over 150 waterfalls in town, it’s no surprise that more than a quarter of a million tourists flock to this area each year. Those who plan to come and admire the town's waterfalls in 2024 will also find a wide range of Ithaca events to attend. For starters, every Saturday between the months of May and October, visitors can enjoy the Farmer’s Market Cruise. Taking off from the beloved Ithaca Farmers Market, the one-hour, narrated cruise sets sail on Cayuga Lake and highlights the lake's rich history. Also the farmers market-Taste of the Finger Lakes 2024 will take place on June 11. The annual food and drink festival is a local staple and raises funds for organizations fighting against food insecurity. But the truth is, no matter when you visit Ithaca, there is always something fun to see and do. Take a stroll through Buttermilk Falls State Park and Robert H. Treman State Park for a day filled with hiking and admiring waterfalls. Those traveling with kids will find fun and educational activities at places like the Ithaca Children's Garden or the Science Center.

Cold Spring

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Nearly 200 miles from Ithaca, along the shores of the Hudson River, travelers will find Cold Spring, New York. Although a rather quiet town with a population hovering around 2,000-Cold, Spring has an abundance of fun activities on offer. Those traveling here in 2024 will want to take advantage of the Summer Series hosted by the Cold Spring Film Society. This annual event takes place at Dockside Park and features free movies under the stars on select summer evenings. Outside of the event, outdoor enthusiasts will enjoy a trip to Hudson Highlands State Park Preserve. The vast 8,000-acre park features over 70 miles of hiking trails, fishing opportunities, and bird-watching areas. Next, head to Storm King Art Center to enjoy a unique and beautiful outdoor art gallery. To wrap up the trip, take in a little local history at The Putnam History Museum.


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Rhinebeck, New York, is another beautiful small town situated on the shores of the famous Hudson River. Located roughly 50 miles from Cold Spring, Rhinebeck is beloved for its thriving local art scene and historic houses. Those traveling here in 2024 will want to plan their trip around the 175th annual Dutchess Fair. Hosted at the Dutchess County Fairgrounds, the fair is notably the second-largest county fair in the state. Here, guests can expect a wide range of entertainment, including food vendors, carnival rides, live music, and livestock shows. After the fair, head to Ferncliff Forest, which features 12 miles of hiking trails, a pond, and an old fire tower that visitors can climb. For a taste of local history, visit places like the Wilderstein Historic Site and the Old Rhinebeck Aerodrome. Finally, dip a toe into the local art scene by paying a visit to the Albert Shahinian Fine Art Gallery.

Lake Placid

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Anyone who loves the Olympics will have a grand time visiting Lake Placid, New York. Known for hosting the Winter Olympic Games in 1932 and 1980, this small town is filled with Olympic charm and natural beauty. In October 2024, Lake Placid is set to host its annual Flaming Leaves Festival at the Olympic Jumping Complex. The festival is designed to highlight the vibrant flame-colored leaves that cover the surrounding Adirondack Mountains. In addition to the stunning views, the Flaming Leaves Festival will also feature a premiere ski-jumping event, food and drink vendors, live music, and crafts. Those who can’t make it in October can enjoy some of the other amenities offered at the Olympic Jumping Complex, including gondola rides and zip line courses. Anyone interested in Olympic history will want to visit the Lake Placid Olympic Museum, which houses the “second-largest Winter Olympic artifact collection” in North America. Finally, top off the trip with more outdoor adventure at The Wild Center. Here, visitors can walk among the treetops on The Wild Walk, go on guided canoe rides, enjoy play areas in the woods, and meet the furry animals who call this place home.


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Oswego, New York, sits on the shores of Lake Ontario, not too far from the Canada/US border. Beloved for its waterfront views, the town offers plenty of fun activities for outdoor enthusiasts. Those looking for 2024 events in Oswego will find a handful of free summer concert series at places like Market Street Square, Veterans Stage, and Breitbeck Park. In July, visitors can enjoy the Oswego Paddlefest, where participants come together to paddle through the New York State Canal System and locks. Outside of those events, visitors can head to Breitbeck Park for an afternoon of lighthouse views, play at the splash pad, and enjoy a round of mini golf. Then don’t forget to take in a race at the Oswego Speedway.


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Montauk, New York, was made for vacations. Situated on the east end of Long Island, this charming small town is home to some of the best beaches and parks in the area. Start a trip to Montauk off right with a visit to the beautiful Shadmoor State Park. The park features a section of Ocean beachfront that stretches for over 2,400 feet. Travelers will also find freshwater wetlands and beautiful bluffs here. As for activities, Shadmoor offers hiking, swimming, saltwater fishing, birdwatching, and picnicking. Next, keep the exploration going at Montauk State Park, where visitors can soak up unbeatable views of the Montauk Point Lighthouse. While here, don’t forget to do a quick browse through the lighthouse museum. Those arriving at Montauk in August of 2024 might be able to catch famous comedian John Mulaney performing at the Montauk Point Lighthouse for a special one-night-only benefit show.

Oyster Bay

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History Buffs, especially those with a fondness for Theodore Roosevelt, will surely have a blast in Oyster Bay, New York. Roosevelt spent many summers here, and today, visitors can explore his old summer home as well as a range of places dedicated to the former president. The summer home, Sagumore Hill, is open for tours and features nature trails and a charming picnic area. After touring the home, head to the Theodore Roosevelt Sanctuary and Audubon Center to enjoy nature trails, educational gardens, and an augmented reality version of Roosevelt himself. Next, check out Theodore Roosevelt Memorial Park, a small beach park offering swimming, rollerblading paths, and courts for a variety of sports. Those arriving at Oyster Bay near the end of June 2024 can sign up for The Oyster Bay Garden Tour. The tour takes guests through four stunning gardens and features an after-tour co*cktail party.

Saratoga Springs

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Anyone looking for a laid-back, relaxing vacation will find the respite they need in Saratoga Springs, New York. The town has long been thought of as a mecca for health and wellness and, as such, has been nicknamed “Queen of the Spas.” Saratoga is home to roughly 21 natural mineral springs-once believed to have healing powers. Today, visitors can admire these springs as they make their way through the city. During a visit here, be sure to check out some of the town's most beautiful nature areas, including The Gardens at Yaddo, Congress Park, and Saratoga Spa State Park. In the state park, visitors will find the famous Saratoga Performing Arts Center. Here, concert lovers will be happy to find a wide range of upcoming 2024 performances, including John Fogerty in June and New Kids On The Block in August.

Fire Island

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Over 200 miles from the healing waters in Saratoga Springs, travelers will find the picturesque barrier island known as Fire Island, New York. The island is home to 17 different communities, a series of protected beaches, and plenty of beautiful areas that are ripe for exploration. Upon arrival, be sure to visit Robert Moses State Park. Here, visitors can enjoy a sunny beach day filled with surfing, boogie boarding, golf, volleyball, and snacking at the concession stand. Next, head to the Sunken Forest, where hiking enthusiasts can wander the boardwalk and admire this “globally rare” area. Anyone who loves lighthouses will also want to take a tour of the Fire Island Lighthouse during their trip. Those visiting Fire Island on July 4, 2024, will be in town for the Fire Island Invasion, where drag queens arrive via boat to perform throughout the island.

Sleepy Hollow

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Anyone who prefers haunted houses and jack-o-lanterns to beaches and waterfalls will find what they’re looking for in Sleepy Hollow, New York. The town is known for the famous tale “The Legend of Sleepy Hollow,” and each year, an estimated 100,000 people flock to this small town, hoping to catch a glimpse of The Headless Horseman. Although busy, October 2024 is easily the best time to visit Sleepy Hollow. During the spooky season, there are a wide range of events to enjoy, including cemetery tours and haunted film festivals. Those who would like a little natural beauty on their trip should also visit Rockefeller State Park Preserve, a gorgeous park just outside of Sleepy Hollow in Tarrytown, New York.

Parting Notes

New York is far more than just New York City. The small towns in this state are chock-full of charm, attractions, and 2024 events. From concerts and comedy performances to drag shows and Olympic jumping events, travelers will never run out of things to do in New York this year.


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Amber Van Wort June 3 2024 in Places

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10 Cutest Small Towns In New York To Visit In 2024 (2024)


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