10 Prettiest Towns In New York
New York is one of the best states to balance diverse settings and atmospheres thanks to its seasonal justified climate, natural richness, extensive history, and proximity to international borders. While its claim to fame is The Big Apple, New York City, not all of the state is as busy and overwhelming, in fact, some of the most laid-back and mind-calming towns to zone out and seek clarity are within the empire state. Why travel to the secluded temples of Japan or the island of Thailand when New York offers the perfect setting to regroup and find your Zen?
Hudson
Sitting at the foot of the Catskill Mountains, this pretty town is a haven of historic architecture; Hudson is the New York town to visit if you want to learn about American history through beauty. Unlike many cities on this list, Hudson attracts few visitors, enjoys a calming atmosphere balancing nature and history, and is surrounded by farmland. Its downtown is dotted with antique stores and small family-owned businesses that have been passed down through generations adding to its traditional American small-town feel. While you can find historical significance in every corner of this charming small-town, famous landmarks include Olana State Historic Site, the Terry Gillette Mansion, and Columbia County Courthouse.
Ithaca
The heart of Tompkins County, sitting along a magnificent backdrop of the Finger Lakes, is the pretty small town of Ithaca that balances a symphony of aesthetically pleasing natural views with along with a strong sense of local community that’s portrayed through local events, festivals, and community gatherings. Additionally, Ithaca is renowned state-wide for being an educational hub and go-to destination for the ultimate college experience. The charming small town makes almost every list of the best small towns in New York and is home to world-class institutions like the esteemed campuses of Ithaca College and Cornell University. Things to do and places to see while in Ithaca include checking out the Cayuga Nature Center and the Herbert F. Johnson Museum of Art, exploring the great outdoors, and appreciating the town’s student-centric atmosphere. Outdoor destinations to explore include the Ithaca Falls, New Feild Covered Bridge, Cascadilla Gorge, and other community-centric destinations like the Ithaca Farmers Market and the Apple Harvest Festival.
Lake Placid
Capitalizing on the natural beauty of the Empire State is the picturesque village of lake placid, which bases its whole atmosphere around its godly gifts of dense forests and clear waters. The quaint town enjoys a cozy vibe that is emphasized by the hospitality of welcoming locals, from small-business owners to tour guides and nature-appreciating residents that you’ll encounter on your hikes and calming scenic walks through the lush lakeside trails. Lake Placid is the perfect all-year-round destination, but it is most visited in the vibrant fall and freezing winter season as tourist scurry to the small town to appreciate the panoramic views of the encompassing Adirondack mountains. Stay near the town’s main street during your visit to Lake Placid, where all locally acclaimed dining and shopping destinations are located. Popular destinations on Main St include Top of the Park restaurant, the Lake Placid Pub & Brewery, and Zig Zag’s live music Pub.
Aurora
One of the smallest, yet liveliest Finger Lakes small towns, Aurora is a classy city escape renowned for being home to one of the best resorts in the area. Inns of Aurora and their Spa are a 15,000 sq foot wellness retreat that has become synonymous with the town's getaway experience, one of the best places to stay when in town. Visitors of Aurora choose the village despite the many charming surrounding options for its waterfront wine-tasting destinations and vineyards like the Long Point Winery, 1833 Kitchen & Bar, and the famous Lakeshore Winery. For the best experience at Auroura, go on locally guided tours like the famous Bianconi Tours, ensuring you get the most out of your stay at Aurora.
Woodstock
Woodstock is a quirky small town that makes every list of beautiful towns for its musical heritage, friendly hippie atmosphere, and distinctive local businesses. The town has a rich history of being both a chaotic and peaceful haven for rock n’ roller’s at different periods, and visitors often stop by to learn more about the hype and get closer to the iconic events that took place in Max Yasgur’s dairy farm 40 miles southwest of the town. Small shops disguised as residential homes, a vibrant art scene, and local street vendors are among the key elements that help Woodstock maintain its unique personality and continue attracting tourists. Embrace the town’s unique setting by visiting its main Tinker St home to Vintage shops like the Rare Bare, Crafty boutiques such as the popular Candlestick, and mouthwatering dining experiences at cafes and restaurants like The Tinker Taco Lab and Little Apple Cafe.
Kingston
The first Capital of New York and a town of historic significance, Kingston is a must-visit for those who find beauty in architecture and cultural attractions. The town offers a classier atmosphere than many destinations on this list of the prettiest small towns in New York and boasts fine dining, antique shops, and lively nightlife as its competitive advantage. Kingston River Maritime Museum, Catskill Mountain Railroad, and the upstate area nicknamed Stockade District are all must-see attractions to get the most out of your visit to Kingston, New York. Aside from its historical richness, Kingston is renowned for having some of the best Bagels in the state, and if you don't know what New York Bagel is, visiting Kingston is the perfect place to learn more about the cultural staple. Sunrise Bagel & Deli, B’n B Bagel, and Kingston Bread + Bar are a few of the many breakfast diners and cafes to start your day during your stay in Kingston.
Sleepy Hollow
Globally agreed-upon as one of the most haunted destinations in the world, Sleepy Hollow sits along the shore of the Hudson River and enjoys one of the most vibrant Fall seasons in the state. The town is a peaceful city escape for those who relax in the presence of a spooky atmosphere as its Victorian building like the Old Dutch Reformed Church and Sleepy Hollow Cemetery, Headless Horseman Bridge, and Lyndhurst Mansion inspire feelings of living in a horror novel. If living within a spooky legend isn't enough, you can check out impressive attractions like the royale-themed Kykuit Estate, Rockefeller State Park Preserve, and the Sleepy Hollow Lighthouse.
Skaneateles
A lake town in upstate New York that makes a perfect family getaway for an extensive range of activities and experiences. From vineyards and wineries to small-business shopping, and boat tours, Skaneateles balances every aspect that other pretty New York Towns differentiate themselves with. Stroll the waterfront Thayer Park, Tour the Finger Lakes Wineries, admire the unique Victorian architecture, and indulge in one of the most inclusive dining experiences. Pastries and Pies will be the delicious highlights of the dining experience best found at locally owned bakeries like The Patisserie and Skaneateles Bakery. However, for the ultimate dining experience, check out the Sherwood Inn, Elephant and The Dove, and Blue Water Grill that serve international cuisine with a touch of local love.
Cooperstown
Home to the National Baseball Hall of Fame, Cooperstown is a naturally abundant small town that boasts a range of well-preserved historic buildings from the 1800s. The town is named after the late famous Author William Cooper, the founding father of the town that purchased the land from bankrupt owners and created a productive society for early settlers. Today, Cooperstown is widely known as a summer resort town that takes pride in its history, narrated through museums, galleries, and businesses that showcase its story as one of America’s most beautiful small towns. Otsego Lake is the town’s main center of attraction and an inspiration for creating a place that stands out from its neighboring areas, nicknamed Glimmerglass by the internationally acclaimed late author. The Farmer’s Museum, Fenimore House Museum, and Fenimore Art Museum are a few of the many locations where you can learn more about the history of Cooperstown during your visit.
Cold Spring
Wrapping up our list of the prettiest towns of New York is the nature-centric destination that perfectly represents the diverse landscape and setting of the Empire State. Legend has it that the town was named after a time when former President George Washington drank from one of the town’s natural springs and suggested it was rather cold. However, that’s not why it makes our list of the prettiest towns. Cold Springs sits along the stretch of Hudson River just 50 mi from New York City, making it a go-to escape from the bustling lifestyle. You can find everything from the restored historical architecture of early settlers to vibrant community gardens and waterfront relaxation spots. The town is perfect for unspoiled wilderness hikes, watersport activities, and fine dining, as it embraces slow life with toned-down nightlife and entertainment options. Dougs Pretty Good Pub, Barber n’ Brew, and Cro’nest are some of the town's most popular hangout places.
Finally, whether you're a local exploring the natural richness of your state, Canadian crossing borders, or a tourist visiting the Big Apple, don't skip exploring New York's pretty small towns. Plan a visit based on what appeals to you, or take the time to go town hopping and indulge in a comprehensive experience of history, nature, and entertainment.
