Early morning view of downtown Ocean Beach on Fire Island, New York

12 Unforgettable Small Towns to Visit in New York

The Empire State houses some real gems beyond the NYC scene, nestled among the nation's most renowned natural treasures. From the Finger Lakes Region to the Adirondacks and the Catskills, there are small lakeside towns and hidden gems like Pawling, situated in the scenic Hudson Valley. In the winter, enjoy magical festivals and skiing opportunities, while summer brings the sun-drenched beaches of Montauk and the Hamptons, and the serene Ocean Beach on Fire Island.

Skaneateles, with its picturesque lakefront, offers an idyllic spot for a summertime picnic at Skaneateles Lake Park. Meanwhile, Geneseo serves as the gateway to Letchworth State Park, the "Grand Canyon of the East," featuring a Victorian downtown set against snow-covered cliffs in winter. These towns are just a few examples of the family-friendly attractions, memorable meals, eclectic shopping scenes, and vibrant art environments found throughout the state.


Small town of Camillus , NY, in upstate New York , early morning after a rain shower
The small town of Camillus in upstate New York , early morning after a rain shower

Nestled near the Forest Unique Area, the small town of Camillus, with a population of roughly 1,250, is an unforgettable destination for outdoor enthusiasts. Ranging from 400 to 710 feet in elevation, this area offers year-round recreational opportunities such as swimming, fishing, camping, hiking, biking, and, during winters with adequate snowfall, skiing and ice skating on the Erie Canal towpath.

The town, just west of Syracuse, enjoys a peaceful atmosphere along the quaint Erie Canal, complete with Federal-style homes ideal for all-season strolls. Unique local spots like Freedom of Espresso and Foster's offer delightful dining and shopping experiences. While not directly on Lake Ontario, Camillus is only about 35 miles from its eastern shore, offering additional opportunities for waterside relaxation and woodland paths in nearby areas like the Three Rivers Wildlife Management Area, which offers cross-country skiing trails in winter and lush hikes in other seasons.


Chittenango Falls in Chittenango, New York.
Chittenango Falls in Chittenango, New York.

Chittenango, the birthplace of L. Frank Baum, author of "The Wizard of Oz," is a magical destination along the Erie Canal. The town embraces its fairytale connection with actual yellow brick sidewalks and numerous photo opportunities. The main museum, All Things Oz, showcases memorabilia from the Oz series, and the annual Oz-Stravaganza in June celebrates the movie's history. The Yellow Brick Road Casino and the Canal Boat Landing Museum further highlight the town's unique character and historical significance. Additionally, Chittenango offers access to the Haunted History Trail of New York, featuring local lore and tragic stories. For a change of pace, the beautiful Chittenango Falls State Park, located just south of the town, offers a scenic waterfall and nature trails to explore.


Historic downtown street of Geneseo, New York
Historic downtown street of Geneseo, New York. Image credit JWCohen via Shutterstock.com

Geneseo impresses with its Victorian architecture, embodying small-town charm in a downtown area that is entirely listed on the National Register of Historic Places. Visitors can explore exhibits at the Wadsworth Library, housed in the former home of James Wadsworth. The town, receiving about 51 inches of annual snow, offers excellent opportunities for cross-country skiing and ice skating along the lake. During the holiday season, don't miss the Dickens Christmas festivities! Enjoy a stroll along Main Street, where Java's Café and unique shops await. The town, serving as the gateway to Letchworth State Park, the "Grand Canyon of the East," offers stunning views of snow-covered cliffs and nearby waterfalls. Conesus Lake, just minutes away, is perfect for exploration and waterside recreation. For a historic stay, consider the 1886 Wadsworth Homestead Inn or unwind at the Diederich Inn.


Downtown view of Geneva, New York.
Downtown view of Geneva, New York. Image credit PQK via Shutterstock.

Located in the heart of New York’s scenic Finger Lakes region, Geneva sits on the northern shore of Seneca Lake, the second-longest and deepest of the Finger Lakes. The town, designated as an All-America City in 2015, is known for its historic charm and picturesque scenery, with flat, rural roads ideal for cyclists and golfers. In summer, the lake is perfect for fishing, boating, and swimming. Geneva's renowned wine and beer trail offers a delightful experience for visitors, featuring award-winning wines and a vibrant history. The town's strong agricultural roots contribute to a thriving local food scene, where restaurants feature an abundance of locally-sourced ingredients. On weekend nights, the "uniquely urban" Linden Street often becomes a pedestrian zone, boasting a variety of culinary options including farm-to-table restaurants, wineries, and craft breweries. Geneva's history dates back to the late 18th century, when it was first settled by European-Americans. It was named either after Geneva in Switzerland, reflecting the lakeside setting, or possibly has origins in Native American language.


Shops on main street Montauk, New York
Shops on main street Montauk, New York

Montauk, a well-known hamlet at the easternmost point of Long Island, is a prime travel destination offering an unbeatable seaside getaway. Situated at the east end of the Hamptons region, Montauk is perfect for leisurely exploration, whether by bike to the historic Montauk Point Lighthouse in Montauk Point State Park or on foot along its scenic streets. Nestled between the Atlantic Ocean and Block Island Sound, Montauk's pristine beaches are ideal for oceanfront stays, fishing, surfing, paddling, and enjoying fresh seafood. Locally known as "The End," Montauk is a vibrant starting point for exploring the state's famed Hamptons. The town boasts family-friendly beaches like Ditch Plains and nature trails, with the Montauk Chamber of Commerce Visitor Information Center on Main Street providing valuable local insights. Montauk's lively atmosphere is perfect for hosting weddings, festivals, and art events. Gurney's Montauk Resort & Seawater Spa adds to the allure with its private beach club and ocean-themed spa.

Ocean Beach

View of Ocean Beach Village coastline on Fire Island
View of Ocean Beach Village coastline on Fire Island, via Marlon Trottmann / iStock.com

Ocean Beach, uniquely situated on Fire Island, offers a distinctive, car-free environment where bicycles and wagons are the primary modes of transportation. This charming oceanside town welcomes visitors with public amenities like basketball courts and ping-pong tables, along with bicycle rentals for exploring its scenic trails. A bike tour or a ride along the beach trails is the perfect way to discover the area, including neighboring Seaview and Ocean Bay Park, and even the gated community of Point O'Woods. The Sunken Forest provides a fantastic hiking experience, and while Heckscher State Park, located off Fire Island, offers wildlife spotting and BBQ facilities. Fire Island Parasail provides thrilling parasailing adventures and private boat tours. Ocean Beach's vibrant commercial district features shops, pubs, and restaurants, where children often sell painted seashells. Peaceful tree-lined walks lead from the bustling commercial district to the tranquil Atlantic Ocean shores, passing envy-inducing homes along the way. The community center, a modern facility on the bay, hosts theater performances and movies, and houses the Ocean Beach Historical Society, further enriching the town's cultural offerings.


Downtown Pawling in New York,
Downtown Pawling in New York, File:Downtown Pawling.JPG - Wikimedia Commons

Located just 1.5 hours from NYC, Pawling is a gateway to the serene and stunning landscapes of upstate New York, blending history with modernity. This town, situated in the Hudson Valley, offers a peaceful retreat from the city, boasting attractions like the vast Appalachian Trail, nearby mountains, and natural preserves. With its country vistas, unique homes, and a quaint village center, Pawling provides a mix of exploration and relaxation. The area features four lakes for summertime recreation and boasts the distinction of having one of the oldest municipality-owned golf courses in the nation. With over 440 acres of parkland, visitors can enjoy the Great Swamp, Nuclear Lake, and the Empire Rail Trail. The Nature Conservancy and the expansive Appalachian Trail offer additional outdoor adventures. Historical tours, including Washington's headquarters, and a helpful Chamber of Commerce Visitors Center, are available to guide tourists through this remarkable area.

Saratoga Springs

Downtown Saratoga Springs in New York
Downtown Saratoga Springs in New York, via Brian Logan / iStock.com

Saratoga Springs, known for its picturesque main street, Broadway, is a town rich in history and charm. Lined with historic buildings, Broadway is a hub of activity, offering hotels, restaurants, bars, shops, and art galleries for endless exploration. The town's main attraction, Saratoga Spa State Park, a 2,400-acre National Historic Landmark just outside downtown, features the Roosevelt Baths & Spa and the Saratoga Performing Arts Center, known for its summer concerts and ballet performances. The Saratoga Automobile Museum and miles of trails, suitable for hiking and cross-country skiing, cater to families and outdoor enthusiasts alike. Saratoga Springs has long been celebrated for its mineral springs, dating back to the late 18th century, and became a prominent resort town in the mid-19th century with the famed Grand Union Hotel. Today, the town offers a lively social scene near the Adirondack Mountains, including speakeasies, music clubs, and the Saratoga Casino Hotel. Visitors can enjoy the famous racetrack and easily access nature from the charming downtown area. For those seeking a spa experience, the Roosevelt Inn and Spa provides a comprehensive hydrotherapy experience with 42 treatment rooms.


Genesee Street in Skaneateles, New York
Genesee Street in Skaneateles, New York, via DebraMillet / iStock.com

This renowned town along the eastern side of Skaneateles Lake is both classic and unforgettable. Often referred to as the "Eastern Gateway to the Finger Lakes," Skaneateles dazzles with stunning nature and magnificent Victorian architecture at its heart, making it an unforgettable getaway for any group and taste! With stately houses along tree-lined avenues, Skaneateles is picture-perfect from every angle, like its lakefront Clift Park with a charming gazebo for a summertime picnic. Its vibrant arts scene enhances everything here, making it a real treat to stroll through the boutiques and art galleries and to enjoy innovative farm-to-table dining.

Effortlessly and without the overcrowded tourist scene, you can enjoy an upscale getaway in the state with a stroll to the lakefront from the historic town, wine tasting at surrounding wineries, and a romantic sunset at the nearby Skaneateles Pier. With 90 inches of snow in the winter, the festive streets and storefronts are covered in a soft blanket, while the lake is ideal for skating against a backdrop of snow-dusted hills in the countryside, perfect for sleigh rides. The downtown restaurants will warm you up and recharge you for another day of wonders, while the Sherwood Inn offers spacious suites to cozy up by the fire!

Sleepy Hollow

A couple crosses at the intersection in downtown Sleepy Hollow in New York state
Shoreline in the village of Sleepy Hollow in New York state. Image credit Andrew F. Kazmierski via Shutterstock

Straight from Washington Irving’s 1820 short story about the wandering schoolteacher Ichabod Crane, Sleepy Hollow is an enchanting little village full of legends and timeless charm. Nestled in a spacious cove among other indents on the eastern shore of the Hudson and only 40 minutes from Manhattan, it is as easy to imagine the encounter with the Headless Horseman here as it is to visit Irving’s final resting place at Sleepy Hollow Cemetery!

Both the old church and the nearby Headless Horseman Bridge are from his story, while the "Galloping Hessian of the Hollow" is a more modern addition on the other side of the bridge. You can take a scenic stroll to the old Sleepy Hollow Lighthouse on the river and take a historically architectural tour of Kykuit, the John D. Rockefeller Estate and his family's residence. The Great Jack O'Lantern Blaze draws people from around the globe for a family-friendly Halloween celebration, among other exhilarating events throughout the year!


Aerial view of Speculator, New York.
Aerial view of Speculator, New York.

Speculator, NY, known as the "all-season vacationland," is a premier destination along the beautiful Lake Pleasant in the southern Adirondacks. Offering a sense of discovery through its vast and pristine surrounding wilderness, the highlights of a weekend trip here include mountain biking and exploring the mysterious Kunjamuk Cave via a well-maintained bike trail. Activities such as hiking, paddling, golfing, boating, and fishing abound, allowing visitors to expand their getaway with great access to backcountry trekking or to the nearby towns of Lake Pleasant, Piseco, and Arietta for day trips.

The business district features an array of shops, including the unique Charlie John's Grocery Store, stocked with camping gear, topographical maps, and other essentials for outdoor adventures. The locally owned Speculator Department Store offers high-quality brand-name products and Adirondack souvenirs. Meanwhile, a variety of cafes and eateries along the roadway provide opportunities to recharge with a quick snack or a hearty, mountaineer-inspired meal. In winter, visitors can enjoy the nearby 750 miles of groomed snowmobile trails and the family-friendly terrain of Oak Mountain Ski Center. In summer, there's excellent swimming and waterside recreation along the picturesque Lake Pleasant.


Trumansburg, New York Main Street
Trumansburg, New York Main Street

Located just outside Ithaca, Trumansburg is a memorable town, boasting one of the Finger Lakes Region’s most impressive natural features, Taughannock Falls. With its charming atmosphere, grand natural scenery, and small-town attractions, Trumansburg even features a chocolate factory! The great outdoors is showcased in Taughannock Falls State Park, which offers spectacular views of Cayuga Lake and other natural vistas, adapting beautifully to every season. The park is perfect for fishing, swimming, and hiking, with trails that transform into snowshoeing and cross-country skiing paths in winter. It also offers summertime camping with tent and trailer sites, including pet-friendly options. Visitors can hike around the gorge and witness the 215-foot-tall waterfall cascading over vertical cliffs. The park is equipped with amenities like showers, grills, picnic tables, and dumping stations, making it family-friendly with opportunities for sledding and staying in cabins.

Nearby, the Inn at Taughannock is a luxurious Victorian-style hotel overlooking Cayuga Lake, featuring a world-class restaurant ideal for brunch or dinner, situated right on the Finger Lakes Wine Trail. Trumansburg is home to beautiful Gothic and Greek Revival architecture and the sapphire-blue Cayuga Lake, offering a visually appealing and winding Main Street with a hip local vibe. The town boasts farm-to-table cafes, vintage shops, bed-and-breakfasts, and pubs. The annual Grassroots Festival in July is a highlight, featuring over 75 bands and performers, along with family-friendly activities such as morning yoga sessions, drum circles, dance workshops, and Sunday's Happiness Parade. Additionally, visitors can enjoy cider at Black Diamond Farm, house-brewed ale at Garrett's in town, and more hiking, biking, and horseback riding in the Finger Lakes National Forest, which offers additional gorges and ravines to explore.

Offering unforgettable adventures and family attractions in every season, the natural surroundings of small towns in New York State present a stark contrast to the Big Apple scene. Each town, like Andes with just over 1,000 locals, dresses up for every season, boasting incomparable leaf-peeping opportunities during the fall. While some towns are nestled amidst the mountains and offer wintertime skiing, others are set along serene lakeshores, perfect for summertime water fun.

Each town, tucked away in a natural crevice, boasts its own unique identity, complete with a wealth of historic sites, legends, and other timeless charms waiting to be discovered. Visitors can explore Washington Irving's gravesite in Sleepy Hollow, also home to Kykuit, the John D. Rockefeller Estate. Alternatively, they can enjoy a gorgeous waterfall just south of the Oz-themed Chittenango, in Chittenango Falls State Park.

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