8 Oldest Founded Small Towns to Visit in New York
New York's history is woven into the fabric of its small towns. These hamlets, some founded as early as the 17th century, offer a unique blend of historical intrigue and modern-day charm. Imagine strolling through streets where Revolutionary War soldiers once marched or exploring vibrant districts that have transformed from bustling trade hubs to artistic enclaves. Each town on this list has its own distinct character, from the maritime legacy of Sag Harbor to the colonial architecture of Kingston.
New Paltz
Set beside the Wallkill River and sheltered beneath the breathtaking Shawangunk Ridge, New Paltz is a gem in Ulster County, renowned for its rich history and natural beauty. This charming town was settled by French Huguenots in the early 18th century, and their legacy can be seen along Historic Huguenot Street, a National Historic Landmark District. Here, visitors can explore seven original stone houses and a reconstructed 1717 church, immersing themselves in the colonial past. Just west of town lies the Mohonk Preserve, offering 70 miles of trails for hiking, biking, and horseback riding. Further west, Minnewaska State Park Preserve features the iconic Mohonk Mountain House, a world-famous resort on the edge of Mohonk Lake.
New Paltz's vibrant Main Street is a hub of quirky attractions and boutique stores, making it a favorite among tourists. The open-air Water Street Market is perfect for those seeking unique souvenirs like sculptures, jewelry, and antiques. History buffs will appreciate the 10-acre Huguenot Street Historic District, home to the 1721 Jean Hasbrouck House and the 1717 Crispell Memorial French Church. For an extraordinary experience, the Victorian-era Mohonk Mountain House offers luxury accommodations, a spa, and exquisite dining amidst 40,000 acres of stunning landscapes.
Southold
Southold, founded in 1640, stands as one of New York's oldest and most captivating small towns. Nestled on Long Island's North Fork, this historic town offers a blend of colonial charm and modern attractions. History enthusiasts will appreciate the Southold Historical Society Museum Complex, featuring restored buildings like the 1750 Thomas Moore House and the 1822 Bay View Schoolhouse. Strolling through these sites transports visitors back to the town's early days.
The town is dotted with boutique shops, art galleries, and exquisite wineries, making it a haven for those who love to explore unique finds and savor local flavors. For nature lovers, the Horton Point Lighthouse and Park offers stunning views of Long Island Sound, perfect for picnics and nature walks. Additionally, Goldsmith Inlet Park provides serene hiking trails and a tranquil beach, ideal for a peaceful retreat. Combining rich history with diverse attractions, Southold offers a memorable and enriching visit.
East Hampton
Located on the South Fork of Long Island and founded in 1648, East Hampton is renowned for its pristine beaches, colonial heritage, and vibrant cultural scene, making it an irresistible destination for visitors. It is one of the earliest English settlements in New York. The town’s Main Street is lined with preserved colonial houses, such as the 1680s Mulford Farm, which offers a glimpse into 17th-century agricultural life. The Home Sweet Home Museum, a 1720 saltbox house, provides further historical insights and is named after the famous song purportedly written there.
In addition to the historic landmarks, The East Hampton Farmers Market is a local favorite, offering fresh produce, artisanal goods, and a taste of the town’s agricultural roots. Additionally, the Pollock-Krasner House, the former home of artists Jackson Pollock and Lee Krasner, showcases the town’s rich artistic legacy. The town is home to some of the most beautiful beaches on the East Coast, such as Main Beach and Georgica Beach, perfect for swimming, sunbathing, and surfing. The scenic Maidstone Park offers tranquil walking trails and picturesque picnic spots, while the LongHouse Reserve features stunning gardens and outdoor art installations, blending nature with creativity.
Southampton
Also located on Long Island's South Fork and founded in the 1640s is Southampton, one of the first English settlements in New York as well. The town’s rich past is preserved in the Southampton Historical Museum, which includes the 1686 Halsey House, one of the oldest English-style houses in the state. The museum offers exhibits that delve into the town’s colonial and Native American history, providing a deep sense of its heritage. Strolling down the historic Main Street, visitors can admire well-preserved colonial architecture, giving a sense of stepping back in time.
Southampton’s commercial scene is vibrant and upscale, catering to a variety of tastes. The town boasts high-end boutiques, art galleries, and gourmet restaurants, making it a shopper’s paradise and a foodie’s delight. The Southampton Farmers Market is a popular spot, offering fresh local produce, baked goods, and artisanal products. The Parrish Art Museum, with its impressive collection of American art, further enriches the cultural landscape.
Southampton is famous for its stunning beaches, including Cooper’s Beach, which is often ranked among the best in the country. The serene environment is perfect for swimming, sunbathing, and beachcombing. Additionally, the expansive Southampton Village Green offers lush landscapes and peaceful walking paths. For a taste of the area’s natural splendor, the Meschutt Beach County Park provides a beautiful setting for picnics, kayaking, and enjoying the waterfront.
Haverstraw
Haverstraw, founded in 1666, played a crucial role during the American Revolutionary War, with the historic Haverstraw Brick Museum highlighting its significance in the brick-making industry, which was once a vital economic activity. Visitors can explore the museum to learn about the town's industrial heritage and the lives of the people who shaped its development. The town’s history is also reflected in its architecture, with many buildings dating back to the 18th and 19th centuries.
If you're an art enthusiast, you will appreciate the Garner Arts Center, a creative space housed in a historic textile mill, offering exhibitions and performances that celebrate local artists and culture. The town also features of delicious dining options as well as the Haverstraw Farmers Market, a local favorite, offering fresh produce, handmade goods, and a taste of the community’s agricultural roots.
The town is situated along the Hudson River, providing stunning waterfront views and recreational activities such as kayaking, boating, and fishing. Bowline Point Park is a beautiful spot for picnics, swimming, and enjoying the scenic Hudson shoreline. The nearby High Tor State Park offers hiking trails with panoramic views of the Hudson Valley, perfect for outdoor enthusiasts.
Huntington
Founded in 1653, Huntington is notable for its well-preserved colonial architecture and deep roots in American history. The Huntington Historical Society manages several historic sites, including the Kissam House Museum and the Soldiers and Sailors Memorial Building, which offer fascinating insights into the town’s colonial past and its role in the Revolutionary War. Walking through the town, visitors can admire numerous 18th and 19th-century buildings, adding to the charming, historic ambiance.
The downtown area is filled with boutique shops, art galleries, and gourmet restaurants. The Paramount Theater is a major attraction, hosting live music, comedy shows, and other performances in a beautifully restored historic venue. For those seeking unique finds, the Huntington Farmers Market offers local produce, artisanal goods, and a lively community atmosphere.
Additionally, Heckscher Park, with its picturesque ponds, walking trails, and gardens, is perfect for a relaxing day out. The park also houses the Heckscher Museum of Art, which features an impressive collection of American and European art. For beach enthusiasts, the nearby Huntington Harbor and Gold Star Battalion Beach offer stunning waterfront views, swimming, and boating opportunities.
Sag Harbor
Located on Long Island’s South Fork, this historic whaling port combines a rich maritime heritage with a vibrant array of commercial and natural attractions, making it an ideal destination for visitors.
Sag Harbor was founded in 1707, and its history is deeply rooted in its whaling past, as it was once one of the busiest whaling ports in the United States. The Sag Harbor Whaling & Historical Museum offers a captivating look into this era, with exhibits showcasing artifacts, scrimshaw, and the stories of the town’s seafaring ancestors. The town's well-preserved 18th and 19th-century architecture, including the Old Whalers' Church, adds to its historical charm and offers a window into the past.
The commercial heart of Sag Harbor is lively and eclectic. Main Street is lined with unique boutiques. The Bay Street Theater, located in the heart of the village, is a cultural hub, hosting live performances, concerts, and film screenings that attract visitors year-round. For food lovers, Sag Harbor boasts a variety of restaurants and cafes, offering everything from fresh seafood to international cuisine. The nearby Mashashimuet Park offers beautiful walking trails, tennis courts, and a playground, perfect for a day of outdoor fun. Additionally, Havens Beach provides a serene spot for swimming and sunbathing, with picturesque views of the bay.
Kingston
Kingston, founded by Dutch settlers in 1652 and later named New York's first capital in 1777, is a historic gem on the west bank of the Hudson River. Despite being burned by British forces during the Revolutionary War, Kingston's rich heritage persists, with buildings like the Old Dutch Church, one of America’s oldest active congregations. The town’s Stockade District showcases well-preserved Dutch Colonial stone houses and historic sites, such as the Senate House State Historic Site, where New York's first state senate met. This blend of historical significance and architectural charm makes Kingston a fascinating destination for history enthusiasts.
Kingston is not just about its past; it has embraced an artistic and cultural revival, particularly in the Rondout-West Strand Historic District. This vibrant waterfront area features a lively promenade with restaurants, galleries, and boutique shops. The Hudson River Maritime Museum highlights Kingston's maritime history, showcasing the town’s significance in trade and transportation. The Kingston Arts District, with its numerous galleries and studios, is a creative hub that hosts regular art walks and cultural events.
In visiting New York's oldest founded small towns, you'll uncover the essence of America's early history and vibrant cultural evolution. From the cobblestone streets of Kingston to the maritime charm of Sag Harbor, each town offers a unique story and a rich tapestry of experiences. Whether you're exploring colonial landmarks, enjoying bustling markets, or immersing yourself in scenic landscapes, these towns provide a captivating blend of past and present, promising an unforgettable journey through time.
