11 Darling Small Towns in New York
Even though the Big Apple often steals all the hype, New York is home to 933 small towns, villages, islands, 62 counties, and various attractions. These destinations carry enthralling histories that keep visitors engaged alongside an array of indoor and outdoor activities that cater to tourists with varying tastes. From the coastal town of Greenport, surrounded by pristine beaches, to Lewiston, which sits along the Niagara River, and Rhinebeck, the home of the first flying museum. Each of these small towns is darling in its own right and definitely ought to be considered on your next visit to the infamous Empire State.
Seneca Falls
American Women's Rights history enthusiasts will love this small town. Nestled between Seneca and Cayuga Lakes is Seneca Falls, a town recognized as the birthplace of the American women’s rights movement.
Start your journey at Women’s Rights National Historical Park, where adventurers can learn more about the movement. Visit the Wesleyan Chapel that held the first Women's Rights Convention in 1848. On-site, check out the homes of leading women and supporters of the movement. The visitor’s center has exhibits and an introductory film on the history of this renowned movement. Stop by the National Women’s Hall of Fame to learn and honor some influential women and their achievements. For more outdoor activities, see Cayuga Lake State Park, where you can camp, picnic, hike scenic trails, swim, and go boating.
Greenport
This scenic coastal town of Greenport offers tourists an array of engaging activities. Start your trip with a tour of the East End Seaport Museum, where visitors learn about Greenport's rich maritime heritage through exhibits, tours, events, and maritime festivals.
Explore Greenport’s coastal beauty through its seaside and surrounding beaches. Go sunbathing, swim, and have a picnic in Sandy Beach, or hike the scenic forest of Orient Beach. Wander through Main Street and check out the charming stores where you can get memorabilia to remind you of your time there. You can also drop by Greenport Harbor Brewing Company to enjoy beer tastings, a guided tour, and good live music in a relaxed atmosphere.
Lewiston
Lewiston is situated along the Niagara River on the Canadian border. Hikers of varied abilities will get to see the picturesque views the Niagara Gorge boasts. You will find it at the Devil’s Hole and Niagara Gorge Rim trails for a slightly challenging hike with beautiful scenery. The Niagara Power Vista Visitors Center features remarkable exhibits and interactive displays that are both entertaining and educational. Tourists can learn about how the technology behind hydroelectric power generation and engage in activities like walking through a turbine and building a dam, among other things. Finish off your day by savoring a meal while overlooking the scenic Niagara River at The Silo.
Sleepy Hollow
Sleepy Hollow offers tourists a unique blend of mystery, history, and natural beauty. This village, formerly known as Tarrytown, adopted its current name in 1996 from the 1820 Legend of Sleepy Hollow and its infamous phantom, the Headless Horseman, by Washington Irving, who resided in Tarrytown at the time.
Sunnyside, the well-preserved home of the famous author Washington Irving, appeals to literature lovers and those interested in his work. Take guided tours as you step back in time to learn about his life. Philipsburg Manor is a living museum that preserves the town's colonial history and allows adventurers to experience life as it was for the enslaved individuals who worked on the property in the 17th century. When you stop by the legendary Sleepy Hollow Cemetery, you can check out the final resting place of Washington Irving, Walter Chrysler, and Andrew Carnegie, among other notable figures. Go on a scenic hike of the Rockefeller State Park Reserve and an alluring overlook of the Hudson River.
Sag Harbor
Visit Sag Harbor for a truly darling and relaxing experience. The Sag Harbor Whaling & Historical Museum houses historic artifacts and objects that reflect the town’s whaling heritage. It also combines contemporary exhibits that display the city’s thriving culture.
Drop by Foster Memorial Beach for a nice walk along the shore, paddleboard, or kayak the calm and pristine waters. Havens Beach is also a fun spot if you want to relax on a picnic with friends and families while watching boats pass by. Elizabeth A. Morton Wildlife Refuge appeals to wildlife enthusiasts and nature lovers alike. Enjoy guided walks in this 187-acre refuge, home to various land and aquatic species, including white-tailed deer, painted turtles, osprey, white-winged scoter, plovers, and terns. Browse beautiful houses, quaint and historic shops, and local stores to shop for unique items when you tour the endearing Main Street Sag Harbor.
Shelter Island
Are you seeking a relaxing getaway from all the hustle and bustle of the big cities? Shelter Island is the perfect destination for you. Surrounded by pristine beaches and a vast ecosystem, this island offers fun activities for everyone.
Start your trip with a hike along Mashomack Preserve, where you get to observe wildlife in this 2,000-acre coastal nature preserve. It is home to various species of birds, mammals, reptiles, amphibians, and insects, and it is lined with tidal creeks, wetlands, and woodlands.
Tourists can enjoy guided tours when kayaking or paddleboarding in Coecles Harbor or West Neck Harbor. They can also stop by Wades Beach for a relaxing swim, a picnic, or a walk on the beach. Their next stop should be the Shelter Island Historical Society, the perfect place to explore the island’s unique history through seasonal exhibitions or a wide collection of historical artifacts and items dating as far back as the 17th century.
Cold Spring
Cold Spring is a village in the Hudson Highlands region. Hikers can enjoy scenic views and a stunning landscape when they tackle Breakneck Ridge, a challenging trail with steep climbs.
West Point Foundry Preserve is an outdoor museum that offers views of the village’s industrial past through ironworks. Go on hikes in Bull Hill, Little Stony Point, and Mount Beacon. Art lovers should see the Magazzino Italian Art Museum, which houses post-war and contemporary artworks with unique features and also has a research library. Dockside Park is another popular spot for relaxing, with scenic views of the Hudson River, a paved square, benches, and a Cannon memorial that honors the town’s history with West Point Foundry. Continue your adventure at Bannerman Castle for guided tours and a glance into its history, or the Boscobel House and Gardens for a tour of this historic mansion and picturesque garden. Stop by Moo Moo’s Creamery for homemade ice cream.
Rhinebeck
Situated in Dutchess County on the east side of the Hudson River is the city of Rhinebeck, which features many well-preserved buildings dating as far back as the 18th century.
Begin with a tour of Wilderstein Historic Site, a well-preserved Queen Anne-style building dating back to the late 1800s that still contains original furnishings, beautiful art, and old family relics. The Old Rhinebeck Aerodrome is the world’s first flying museum, home to a vast collection of flying aircraft from the Pioneer, World War I, and the Golden Ages of Aviation. It also hosts air shows and also has a vintage gift shop. Ferncliff Forest is a great destination with scenic trails for hikers and outdoor lovers. Dine farm-to-table meals at Terrapin Restaurant, which also has vegan options. Shop for a wide collection of books that appeal to all readers at Oblong Books.
Woodstock
The town of Woodstock appeals to nature lovers, art connoisseurs, and music enthusiasts alike. Explore numerous galleries, such as Clouds Gallery, Woodstock Byrdcliffe Guild, Woodstock School of Art, and J Bliss Studios (a jewelry gallery), that showcase unique artworks by both local and international artists and represent Woodstock's thriving art scene.
Take a scenic hike along the Overlook Mountain trail, which offers picturesque views of the Hudson Valley, ruins of an old hotel, and a historic fire tower. Hike the wooded Sloan Gorge Preserve, which is home to various species of birds and plants. Other hikes include the Comeau Property and the Thorn Preserve. Enjoy a taste of Italian cuisine in a restored farmhouse when you stop by Cucina. Call it a day at The Woodstock Inn on the Millstream, a bed and breakfast that provides different lodging options to guests.
Fire Island
Fire Island is welcoming to those seeking outdoor adventures. The absence of cars makes it a perfect getaway destination for adventurers who love biking and hiking.
Explore the Sunken Forest, a globally recognized rare ecological community dating back about 300 years. This Forest can be accessed through boardwalk trails that overlook picturesque views of various plants and are perfect for birdwatching. Surfers of all skill levels will love the pristine waters and great waves of Point O’ Woods, Atlantique Beach, Fair Harbor, Ocean Beach Jetties, and Cupsogue, amongst a variety of other spots. Traverse various communities on Fire Island, such as Cherry Grove, which has beautiful art scenes and lovely restaurants; Fire Island Pines, an upscale resort community, Saltaire with its family-friendly atmosphere; and the boaters’ community of Davis Park, to mention a few.
Skaneateles
Skaneateles is often referred to as the Jewel of Finger Lake. This small town blends history and modernity, attracting both residents and tourists. Walk or cycle the Skaneateles Lake Watershed Trail, taking in the scenic views of Skaneateles Lake.
Travel back in time to the Skaneateles Historical Society, which holds a collection of artifacts reflecting the town’s rich heritage in transportation, local agriculture, and other cultural heritage. Visitors can also take walking tours to see historic buildings and architecture, like the Thayer House. Relish a glass of estate-crafted wine or spirits from Angela’s Vineyard, a local vineyard. Right in the middle of downtown Skaneateles is Clift Park, a fancy park with stone benches, a gazebo, and a pristine lake with beautiful boats. It is perfect for relaxing. From the skies, you will get to see Skaneateles and surrounding areas while enjoying a hot air balloon ride from either Finger Lakes Ballooning or Balloon Rides Over Syracuse. Rest for the day at The Sherwood Inn, a historic inn built in the 1800s that reflects the town’s historic architecture. It also has dining options for guests.
What a ride! These beautiful towns and villages are the perfect weekend or week-long getaway destinations. Prepare to explore the countryside of New York, surrounded by lakes, preserves, beautiful mountains, and picturesque landscapes. Whether you choose Seneca Falls for its Women’s Rights activism, Sag Habor for its rare aquatic species, or Woodstock for its plenteous galleries, you are sure to have a great time in these darling small towns!
