9 Prettiest Upstate New York Towns to Visit in 2024
When you think of New York, chances are New York City comes to mind. However, New York State extends for many miles beyond “The Big Apple,” and this region has some of the prettiest and most charming towns, with picturesque landscapes and historic architecture. If you love history and the outdoors, Upstate New York has the most wonderful offerings, ideal for a family or friend vacation.
Upstate New York differs from the rest of the United States because it offers countryside landscapes and breathtaking views. It’s an ideal place to take a scenic road trip or simply visit one charming town in the region and enjoy it to its fullest.
If you’re in search of an entertaining yet relaxing vacation filled with endless natural beauty, consider one of these nine pretty little towns in Upstate New York. They are each unique in their own way, but all have much to offer, no matter what season you choose to visit.
Skaneateles
Skaneateles is an affluent little town in Upstate New York. Its name comes from the Iroquoian term for “long lake,” as it sits next to the long Skaneateles Lake. This attractive town is known for its awe-inspiring views of fall foliage around the area. It is also a popular destination for travelers looking to go wine tasting. The town offers charming B&Bs and historic inns as accommodations for visitors, and they can also enjoy a stream of delectable restaurants in the historic downtown area.
Cyclists flock to Skaneateles for a 32-mile cycling trail around the lake. If you’re considering coming to Skaneateles later in the year, don’t miss the annual Dickens Christmas celebration starting on Thanksgiving weekend. This event offers live entertainment, carriage rides, and caroling at the gazebo. If you have a few extra days, drive around the surrounding region to explore beautiful hiking trails, historic architecture, and the Underground Railroad.
Saugerties
This quaint town is only a two-and-a-half-hour drive from bustling New York City. It is located on the beautiful Hudson River and boasts stunning views of the Catskills Mountains. Spending a few days at the foot of these pristine mountains is one of the best ways to unwind from daily life.
Travelers enjoy the serene natural habitat that Saugerties has to offer. They can take in the view of the surrounding area from the famous Saugerties Lighthouse or explore the town's vast history at a museum. Several local restaurants and boutique stores are also in and around the core area of the town.
Saugerties has many events to look forward to. One of the most prominently known is the annual Hudson Valley Garlic Festival, which is hosted every September in the heart of the town. The streets are filled with farmers, vendors, tourists, culinary experts, and locals.
Watkins Glen, New York
If you’re looking for the ideal lake town for your next vacation, look no further than Watkins Glen. This small and sleepy town magnificently showcases the beauty of the Finger Lakes region. Watkins Glen is loved by many of its visitors as it offers the perfect spot to relax or fill your days with activities in the area.
If you’re interested in the latter, visit Watkins Glen State Park, a park just inside the town of Watkins Glen. Here, you can enjoy a day of hiking while appreciating cascading and pure waterfalls as you move through the trails. Visitors can enjoy water sports like kayaking. You can spend a day fishing or even apple picking. The options are endless! The town itself also allows you to enjoy an array of fine food and wine from various wineries around the Finger Lakes.
Poughkeepsie
Poughkeepsie is a small town nestled in the Hudson River Valley region. It forms the midpoint between the New York City metropolitan area and Albany, the state capital. The town has quite a history, once referred to as "The Queen City of the Hudson." It was first settled by the Dutch in the 17th century and served as the second capital of New York State not long after the American Revolution.
Today, Poughkeepsie is best known to tourists for one of the world’s largest pedestrian bridges, the Walkway over the Hudson. Visitors can walk over the bridge while enjoying the remarkable view of the Hudson River. If you decide to vacation in Poughkeepsie, explore the downtown area to shop at a plethora of local boutique stores for souvenirs. If you love architecture, be sure to stop by the Bardavon 1869 Opera House, a theater with a range of music, dance, drama, and film events throughout the year. It is also home to the Hudson Valley Philharmonic Symphony Orchestra.
Saranac Lake
Saranac Lake is a quaint little town that offers its visitors the most fantastic mountain views. It is known to be a wonderful alternative to Lake George and Lake Placid, especially if you’re looking for an affordable and quiet vacation spot.
This mountainous gem offers everything you need. Enjoy the superb Adirondack Mountains while still being at the lake. Tourists can enjoy everything from jet skiing and mountain trail hiking in the summertime to tubing in the winter. This small town and its scenic beauty will surely provide an unforgettable experience. Saranac Lake has a tiny population of just over 4,000, making it the ideal space for remote getaways.
Croton-on-Hudson
This attractive small town is located along the Hudson River village and is known for its serene natural beauty. From the moment you drive into the town, you immediately see a beautiful arch bridge over a dam—just the kind of landscape you need for a getaway.
Once you reach the town of Croton-on-Hudson, you’ll notice there is much to choose from in terms of activities. Outdoor enthusiasts can visit Croton Gorge Park, boasting over 90 acres of nature trails and pristine beaches. New Croton Dam is a lovely area filled with recreational activities near the dam. Here, visitors can relish picnicking, hiking, and cross-country skiing. The town hosts an array of annual events, such as Clearwater’s Great Hudson River Revival, which is usually hosted in June. You can learn more about this town’s culture and history at the Van Cortlandt Manor Museum.
Wilmington
If you’re a nature lover looking for the right spot to vacation in Upstate New York, Wilmington is the answer. This small town is absolutely stunning, sharing natural mountainous views from every corner. And if you’re not a hiker, you’ll be happy to know these views can be seen from the town itself.
Taking a drive to Whiteface Mountain will definitely be worth the trip. Here, you’ll get to see epic views of the spectacular mountain range. If you enjoy the sound of waterfalls, be sure to visit High Falls Gorge. Wilmington is a favorite to see in both the warmer and cooler months, as the town offers an abundance of activities like hiking, skiing, and snowboarding. It’s an ideal place for both adults and kids, thanks to all these available activities and more in the area.
Alexandria Bay
The striking town of Alexandria Bay is located in the Thousands Islands region. The town is a wonderful escape from a busy life and gives you the opportunity to explore so much in a wonderful place. Alexandria Bay offers over 1,000 little islands for you to discover and enjoy. And if that’s not enough to keep you busy, you can spend your days touring castles in the area, like the Boldt Castle, with its 120 rooms, including its yacht yard.
Alexandria Bay is a water-based town that lets its visitors explore the waterways by boat or kayak. There are also many lovely state parks to visit. Cultural enthusiasts can spend their days exploring the downtown area and enjoying the Cornwall Brothers Museum.
Catskill
Catskill is a scenic town that runs along the Hudson River, and is located south of Albany. The first advantage to staying here is the views of the Catskill Mountains, a glorious scene for anyone looking to take a deep dive into nature. The west side of the Hudson River is where the Catskill Village is located, the optimal spot for a relaxing vacation. Here you can cycle or hike over the Rip Van Winkle Bridge, a six-mile bridge running over the Hudson River and connecting the Catskills to the Hudson town. The Dutchman’s Landing Park is a great spot for a picnic or for renting a boat for the day and enjoying the crystal-clear waters.
The Catskills area is bountiful with history, and you can enjoy the wonderful downtown area to learn more about what this small town has to offer. Enjoy a coffee at a local café, have lunch at a unique local restaurant, or shop at one of many stores around the town. Visit the Thomas Cole National Historic Site for a dose of Catskill history.
Explore Upstate New York’s Picturesque Hidden Gems
Upstate New York has much to offer, and each of these small towns has unique activities and attractions for tourists coming their way. The best part about these towns is that each and every one of them is nature-rich, making them the perfect getaway spot, especially if you’re tired of the buzzing daily city life. Take a break from the hustle and bustle and drive up to Upstate New York for a vacation filled with scenic trails, glorious mountains, and striking rivers and lakes. All you have to do is pick a town, pack your bags, and say hello to a new and wonderful adventure that awaits.
