Upstate New York’s 9 Most Underrated Towns To Visit

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Upstate New York is brimming with charming towns that often fly under the radar. Beyond the well-known destinations, there are hidden gems that offer unique experiences, stunning scenery, and rich history. This guide highlights nine of the most underrated towns in Upstate New York; each with its own distinct character and attractions. These towns are worth visiting if you’re seeking outdoor adventures, cultural discoveries, or a peaceful getaway.

Cooperstown

Found in the heart of Upstate New York, Cooperstown is a hidden gem that promises both interesting history and outdoor adventures. Here are key attractions to explore:

  • National Baseball Hall of Fame: Begin your visit at the National Baseball Hall of Fame, a must-see for any sports enthusiast. This iconic museum offers a comprehensive exploration of baseball history with exhibits that captivate all ages. From legendary players to memorable moments, the Hall of Fame provides an immersive experience into America’s favorite pastime.
  • Glimmerglass State Park: After exploring sports history, head to Glimmerglass State Park, known for its scenic beauty and outdoor activities. The park features sandy beaches and lakeside trails perfect for hiking, swimming, or simply relaxing by the water. Its natural beauty makes it an excellent spot for picnicking, wildlife watching, and enjoying the great outdoors.
  • Otesaga Resort Hotel: For a touch of luxury, book a stay at the Otesaga Resort Hotel, a waterfront accommodation offering stunning views and excellent amenities. This elegant resort provides an ideal retreat after a day of exploration, with its charming atmosphere and top-notch service. The hotel’s historical ambiance perfectly complements the heritage of Cooperstown.
  • Fenimore Art Museum: Explore the Fenimore Art Museum, which houses a remarkable collection of American folk art, Native American artifacts, and fine art. The museum’s exhibits provide a deep dive into the region’s cultural history and artistic heritage. Its picturesque setting along Otsego Lake enhances the cultural experience.
  • Farmers’ Museum: Visit the Farmers’ Museum, one of the oldest rural life museums in the country, offering a glimpse into 19th-century farm life. The museum features historic buildings, interactive exhibits, and live demonstrations, making it an engaging and educational experience. It provides insight into the agricultural roots and historical lifestyle of Upstate New York.
  • Hyde Hall: Step back in time with a visit to Hyde Hall, a neoclassical country mansion and National Historic Landmark. The well-preserved estate offers guided tours that showcase its architectural splendor and historical significance. Hyde Hall’s beautiful grounds and intriguing history provide a fascinating glimpse into 19th-century aristocratic life.

Narrowsburg

Perched alongside the scenic Delaware River, Narrowsburg offers an enchanting blend of natural beauty and cultural richness. This hidden gem is perfect for outdoor enthusiasts and culture seekers alike. The sprawling Delaware River provides a picturesque setting ideal for kayaking, fishing, and hiking. Don’t miss Hawks Nest, a nearby scenic highway offering breathtaking views of the river and surrounding landscape—a must-see for any visitor.

Narrowsburg isn’t just about the great outdoors. The town boasts a variety of cultural attractions and a burgeoning culinary scene that are sure to delight visitors. Here are some must-visit spots:

Local Galleries

Narrowsburg is home to quaint galleries showcasing the works of local and regional artists. These galleries offer a glimpse into the vibrant arts scene, featuring everything from contemporary pieces to traditional crafts. Exploring these galleries provides a cultural experience and an opportunity to support local artists.

Narrowsburg Union

This historic building has been transformed into a community hub, housing art exhibitions, events, and workshops. The Narrowsburg Union is a testament to the town’s commitment to preserving its history while fostering a vibrant arts scene. Visitors can enjoy various cultural activities and engage with the local community.

Fort Delaware Museum

The Fort Delaware Museum is a reconstructed fort from the French and Indian War era. The museum offers interactive exhibits and reenactments that bring the 18th century to life. It’s an educational and engaging experience for history buffs and families alike.

The Heron Restaurant

When it comes to dining, The Heron stands out for its delicious farm-to-table cuisine. This restaurant offers fresh, locally sourced ingredients that make every meal memorable. With its cozy ambiance and innovative menu, The Heron is a must-visit for food enthusiasts.

Local Eateries and Cafés

Narrowsburg features various dining options catering to diverse palates. From casual cafés to fine dining establishments, the town’s culinary scene is both vibrant and accessible. Each eatery prides itself on using fresh, local ingredients, ensuring a delightful dining experience.

Narrowsburg Farmers Market

Visit the Narrowsburg Farmers Market to taste local produce and artisanal goods. The market is a gathering place for the community, offering fresh fruits, vegetables, baked goods, and more. It’s a great spot to sample local flavors and meet the people behind the produce.

By exploring these cultural attractions and culinary delights, you’ll experience the history and arts scene that make Narrowsburg a unique and charming destination.

Pawling

Pawling offers a charming escape with easy access from NYC, ideal for a spontaneous weekend getaway. This hidden gem in Upstate New York boasts a variety of outdoor activities that cater to adventurers and nature lovers alike. Whether you enjoy horseback riding through scenic trails or hiking in the lush countryside, Pawling provides ample opportunities to reconnect with nature.

The town’s inviting atmosphere is enhanced by its friendly community and delightful local spots. Don’t miss brunch at McKinney & Doyle, a popular dining venue renowned for its delicious food and warm ambiance. After a day of exploring, unwind at Daryl’s House, a well-known live music venue that attracts both locals and tourists. Here, you can enjoy live performances in a cozy setting, making your evening truly memorable.

Pawling’s diverse range of activities offers something for everyone. From outdoor adventures to cultural experiences, it seamlessly blends the best of both worlds. If you’re looking for a weekend getaway that provides both relaxation and excitement, Pawling should be at the top of your list.

Millerton

When you visit Millerton, you’ll be enchanted by its vibrant local arts scene and charming historic district. Enjoy farm-to-table dining that showcases the town’s dedication to fresh, local ingredients. This hidden gem seamlessly blends culture, history, and culinary delights for an unforgettable getaway.

Thriving Local Arts Scene

Millerton’s vibrant local arts scene offers an enjoyable experience for art enthusiasts. The town is home to galleries showcasing works by talented local artists, providing insight into the region’s unique creative spirit. Regular cultural events, such as art walks and exhibitions, immerse visitors in the artistry and passion that define this charming town. These events transform Millerton into a bustling hub of creativity, attracting visitors from near and far.

As you explore Millerton, you’ll encounter stunning art installations, sculptures, and murals that adorn the town, each piece telling its own story. Artisan markets and craft fairs occur throughout the year, offering opportunities to purchase handmade goods and support local artists directly. These markets are ideal for finding unique pieces that you won’t find elsewhere.

Quaint Historic District

Situated in the heart of this charming town, Millerton’s historic district offers a unique blend of history, culture, and community. Here, well-preserved streets dating back to the mid-1800s are lined with distinctive shops and local restaurants. Walking through this district feels like a journey back in time, with beautifully maintained architecture at every turn.

The shops in Millerton’s historic district present an eclectic mix of antiques, artisanal crafts, and local treasures. Whether you’re searching for a rare find or just browsing, the variety is impressive. After a bit of shopping, indulge in a meal at one of the local restaurants, known for using fresh, local ingredients to create both delicious and memorable dining experiences. What truly sets Millerton’s historic district apart is its welcoming atmosphere. The community frequently hosts events that bring residents and visitors together, enhancing the town’s appeal as a hidden gem.

Farm-to-Table Dining

Millerton’s vibrant farm-to-table dining scene offers a delightful experience for any food enthusiast. Placed among the charming Upstate New York towns, Millerton stands out with its commitment to fresh, locally sourced ingredients. This showcases the bounty of the region’s farms. Here are some must-visit spots:

  1. Harney & Sons Tea Room: Begin your culinary journey at the Harney & Sons Tea Room, known for its high-quality teas and delightful dining options. This flagship store features a dining spot where you can savor dishes made with local produce. Enjoy a relaxing meal while sipping on expertly brewed tea in a cozy, inviting atmosphere.
    1. Irving Farm, New York: A staple in Millerton, Irving Farm offers a cozy café experience with a focus on locally roasted coffee and fresh, seasonal ingredients. Their menu includes a variety of breakfast and lunch options, all made with the finest local produce. It’s the perfect spot to enjoy a hearty breakfast or a light lunch.
    2. 52 Main: For a taste of upscale dining, visit 52 Main, which features a diverse menu of tapas and small plates made from locally sourced ingredients. The restaurant offers a warm, inviting ambiance and a selection of fine wines to complement your meal. It’s an excellent choice for a leisurely dinner with friends or family.
    3. The Oakhurst Diner: The Oakhurst Diner offers a classic diner experience with a modern twist, emphasizing locally sourced ingredients. From hearty breakfasts to delicious burgers and sandwiches, the diner provides a comforting and satisfying meal any time of day. Its retro vibe and friendly service make it a beloved spot for both locals and visitors.

Rosendale

Rosendale

When you’re in Rosendale, make sure to walk the Historic Rail Trail for a serene and scenic experience. The highlight is the Rosendale Trestle Bridge, offering stunning views of the surrounding landscape. It’s the perfect spot to appreciate the town’s natural beauty and history simultaneously.

Historic Rail Trail

Explore the Historic Rail Trail in Rosendale, a picturesque 24-mile linear park ideal for walking, biking, and horseback riding. Built on an old rail corridor, this trail is a haven for outdoor enthusiasts seeking a blend of scenic beauty and historical charm. The Historic Rail Trail is part of the larger Wallkill Valley Rail Trail system, making it a crucial connector in the region’s extensive network of trails. The surrounding natural beauty is enriched by the trail’s historical significance, immersing visitors in the tranquil ambiance of Rosendale’s lush landscapes. It’s an ideal destination for nature lovers and history buffs alike.

Rosendale Trestle Bridge

Standing 150 feet high and stretching 940 feet long, the Rosendale Trestle Bridge offers breathtaking views of Rondout Creek and the lush Hudson Valley landscape. This historic railroad bridge, now part of the Wallkill Valley Rail Trail, is a gem in Upstate New York. Whether you’re walking, biking, or simply soaking in the scenery, the bridge provides an unforgettable experience.

Transformed into a pedestrian and cycling path, the bridge is a unique spot for outdoor enthusiasts. Nature lovers, photographers, and history buffs alike will appreciate its panoramic vistas and storied past. It exemplifies how historical structures can be repurposed for modern enjoyment.

Activity Experience Highlights
Walking Leisurely stroll Scenic views of Rondout Creek
Biking Cycling adventure Long stretches, easy terrain
Picnicking Relaxed outdoor meal Picturesque surroundings
Photography Capturing moments Stunning natural and historic scenes

Wassaic

Wassaic

Found in Upstate New York, Wassaic offers a charming blend of history and small-town allure. This quaint town, part of the larger towns of Wassaic and Amenia, exudes an old-timey charm that invites you to explore its past and cozy atmosphere. One of the highlights of Wassaic is its intriguing charcoal kilns, which serve as a testament to its historical significance. These kilns add a unique touch to the town, making it a fascinating destination for history buffs and casual visitors alike.

Beyond its historical elements, Wassaic offers a variety of experiences that make it a true hidden gem. You can enjoy a night out at the drive-in theater, a nostalgic experience that’s hard to find in today’s fast-paced world. For a taste of local flavor, visit the Kings Highway Cider Shack, where you can savor some locally crafted cider.

Stone Ridge

Located just a short drive from Wassaic, Stone Ridge is celebrated for its romantic architecture and idyllic landscapes. As you explore the town, you’ll be captivated by its historic buildings, which evoke a sense of a bygone era. Stone Ridge also boasts a vibrant local food scene, making it a haven for culinary enthusiasts. Be sure to dine at Butterfield, where farm-to-table dishes showcase the region’s finest ingredients.

Outdoor activities are plentiful in and around Stone Ridge. For an immersive experience, visit Stone Ridge Orchard. This local gem is ideal for picking up picnic supplies and fresh produce. Spend the afternoon apple picking or simply unwind in the orchard’s peaceful setting. Its picturesque scenery and unhurried pace make it perfect for unwinding. Whether you’re wandering the charming streets, savoring the local cuisine, or enjoying the outdoors, Stone Ridge offers a serene escape from the hustle and bustle of everyday life.

Hudson

Hudson

Hudson offers a compelling blend of art, culture, and scenic beauty that invites visitors to explore its vibrant community. Found along the Hudson River, this charming town in New York State boasts stunning river views that enhance its picturesque appeal. Here are some must-visit spots:

  • Historic Buildings: Hudson is a treasure trove of historic buildings, each narrating a unique chapter of the town’s interesting past. Walking through the city, you’ll encounter architectural gems that reflect various periods and styles. These buildings offer a tangible connection to Hudson’s history and add to its charming ambiance.
  • Art Galleries and Antique Shops: Immerse yourself in Hudson’s thriving arts scene by visiting numerous galleries and antique shops scattered throughout the town. You’ll find various contemporary and traditional art reflecting the town’s creative spirit. These venues provide a deep dive into the local art culture and offer unique finds for art enthusiasts and collectors.
  • Olana State Historic Site: The cultural attractions extend to sites like the Olana State Historic Site, where you can explore the former home of landscape artist Frederic Edwin Church. This historic site offers breathtaking views and insights into the Church’s life and work. It’s a must-visit for anyone interested in art, history, and scenic beauty.
  • FASNY Museum of Firefighting: The FASNY Museum of Firefighting offers another intriguing experience, showcasing firefighting history and heritage. This museum provides interactive exhibits and displays that educate and entertain visitors of all ages. It’s an engaging stop that highlights an important aspect of community history.
  • Music Festivals and Events: The town’s lively music festivals and events further highlight its artistic community, making every visit an enriching experience. These events showcase local talent and bring the community together in celebration of music and culture. They add vibrancy to Hudson’s cultural landscape and offer entertainment for all visitors.

Tannersville

Frequently overlooked by travelers, Tannersville offers stunning mountain views and a wealth of outdoor activities for nature enthusiasts. Nestled in the Catskill Mountains, this charming town provides a serene getaway with its picturesque setting. Whether you’re an avid hiker or a skiing enthusiast, Hunter Mountain is your go-to destination for various outdoor activities. In warmer months, explore hiking trails that offer breathtaking scenic mountain views, while winter transforms the area into a skier’s paradise.

After a day of adventure, head over to Twin Peaks Coffee & Donuts for a delightful treat. Their fresh, homemade donuts and coffee are the perfect way to recharge. You’ll also appreciate the town’s unique charm and hospitality, epitomized by the historic Last Chance Antiques & Cheese Cafe. This quirky spot offers delicious food, unique antiques, and an extensive selection of cheeses, making it a must-visit. Tannersville seamlessly combines natural beauty with local charm. It’s an ideal destination for those looking to escape the hustle and bustle while indulging in both recreational activities and cozy, small-town comforts.

Conclusion

Exploring the underrated towns of Upstate New York reveals a side of the state that is full of surprises and delights. From picturesque landscapes to vibrant local cultures, these towns offer something for everyone. By venturing off the beaten path, you’ll discover the true charm and beauty of Upstate New York. Plan your visit to these hidden gems and experience the rich tapestry of history, nature, and community that they have to offer. Don’t miss out on exploring these unique gems! 

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