12 Unforgettable Small Towns to Visit in Upstate New York
Upstate New York, comprising New York State’s northern areas, is a haven for scenery and culture. The region boasts some of the country’s finest natural landmarks, from the Catskill Mountains to the Finger Lakes. With four distinct seasons, Upstate New York offers a delightful variety of activities, from basking in summer's warmth to embracing the snowy landscapes of winter. The region is also home to some of the most iconic small towns, such as Cooperstown and Ithaca. These towns are perfect destinations, showcasing the area's stunning art, history, and nature. Far from the crowds of urban hubs, they offer visitors a relaxing way to get authentic experiences.
Canandaigua
Canandaigua in Ontario County is a mix of everything that makes Upstate New York amazing. From the serene Canandaigua Lake to the friendly locals, there are various ways to enjoy the town. Nature enthusiasts adore the lake, which is a picture of tranquility. Surrounded by attractions like the City Pier, Kershaw Park, and Canandaigua Country Club, the possibilities are endless. Head out paddleboarding, play a game of golf, or hike along a lakeside trail to indulge in the beautiful environment. Besides Canandaigua Lake, this town is also known for its vibrant streets.
Visitors interested in this side of Canandaigua should tour the historic downtown area for its array of galleries, landmarks, and restaurants. For example, the Sonnenberg Gardens & Mansions State Historic Park and CMAC concert venue are overflowing with culture. The Sonnenberg Gardens & Mansions State Historic Park is over 100 years old, and touring the 40-room Queen Anne-style mansion is a trip back in time. A short drive away, CMAC is a more lively attraction, hosting famous artists like Cody Jinks and Oliver Anthony throughout the year. Afterward, end the day with a delicious cheeseburger at the Green Front restaurant. It will make your time in Canandaigua unforgettable.
Catskill
As the name suggests, Catskill is a town nestled within New York’s Catskills region. Famed for its natural allure, tourists from all over flock to town for its outdoor opportunities, especially at the Kaaterskill Wild Forest. This 7,000-acre abode of nature is flush with all sorts of sights, such as thick forests, rolling hills, and flowing rivers. Hiking is among the top activities here with various unique trails to explore in the region. Beginners should attempt the 2.7 mile (4.3 km) Inspiration Point route which is a simple walk engulfed in pretty flora and fauna. Meanwhile, advanced hikers can challenge themselves on the steep Kaaterskill High Peak Trail. It's a 7.8-mile (12.6 km km) trail that takes one to a stunning viewpoint showcasing the entire area. Keep your eyes peeled on these trails as you might spot a bobcat, coyote, or mink which often come up. In addition to this, the Catskills are ideal for cycling, fishing, and bird-watching for endless fun.
Back in town, Catskill exudes a charming vibe where visitors can feel at home. Roam the tapestry of vibrant streets for a new experience at each corner. While some streets may showcase colorful architecture, others are full of art galleries. That said, one thing is common, the 11,300 friendly residents. Always greeting people with a smile, stop by the authentic Left Bank Cider or Thomas Cole National Historic Site for a warm welcome. Great food, interesting stories, and fun conversations abound, Catskill is a must-visit destination in New York.
Cooperstown
Any list of towns in New York State is incomplete without the county seat of Otsego County, Cooperstown. Home to 1,800 residents and plenty of streets teeming with life, the town is a hub of tourist entertainment. Visiting Main Street is worth it thanks to the vintage buildings, historic streetlamps, and cultural attractions. Roaming around, some landmarks are sure to stand out, such as the National Baseball Hall of Fame and Museum. This 90-year-old history museum and hall of fame is the holy grail for baseball fans, with hundreds of artifacts and exhibits on display. Similarly, the Farmers’ Museum, Glimmerglass Opera, and Fenimore Art Museum showcase different sides of the town, from iconic musicals to pristine paintings.
As you spend the day clicking pictures and roaming around, you are sure to get tired. Thankfully, there are tons of eateries here, full of energy and good food to keep you recharged. Coffee lovers can grab an espresso at Stagecoach Coffee while pasta lovers should book a table at Nicoletta’s Italian Cafe.
The fun in Cooperstown is not only limited to paved streets. During the summer months, Otsego Lake comes to life, spanning the entire northern boundary of town. Swimming, fishing, and boating are a few ways to take advantage of the calming waters. Moreover, the lake is lined with outdoor parks, where hiking, camping, and biking are popular activities with tourists. Put it all together and Cooperstown is a perfect destination for all kinds of visitors.
Saratoga Springs
If you liked the vibe of Cooperstown, this town should be next on your list. Named after its mineral springs, Saratoga Springs is a popular resort destination in Upstate New York. Upon arrival, a blast of culture greets tourists, which is palpable through the array of landmarks all around. For example, horse racing fans rejoice at sights like the Saratoga Race Course and the National Museum of Racing and Hall of Fame. Whether it is watching a race live or learning about the competitive sport, these places are full of thoroughbred racing charm. The Saratoga Performing Arts Center is also worth visiting with events such as the Saratoga Wine & Food Festival which are full of life. Even if these sights don’t interest you, the town’s 28,500 residents and array of shops will keep anyone busy for days.
The true charm of Saratoga Springs lies in its mineral springs which are believed to have healing properties. Congress Park and Congress Springs is one of the town’s most famous springs, boasting a relaxing pavilion and soothing views. Adventurers can hop into the water as their minds and bodies release any stress. Moreover, beautiful flora and walkways surround the springs, creating a mystical environment like no other.
Geneva
Along with its name, this idyllic New York town shares many similarities with its Swiss counterpart. Resting on the northern end of Seneca Lake, natural beauty is abundant, and there are ample ways to take in the sights. Most tourists head straight to the lake which is a reprive of Mother Nature’s allure. Fishing is one of the most popular activities, which has earned Geneva the nickname, “Lake Trout Capital of the World.” Plan your trip in May to attend the National Lake Trout Derby, a competition where anglers from across the country compete for the largest catch. If not fishing, hiking trails, kayak rentals, and lakefront concerts create a wonderful environment full of energy.
As you walk back into town, an air of romance is evident no matter where you go. The best example, of this is Belhurst Castle, an 1800’s castle that is now a hotel and winery. Visitors can stay the night in this medieval building with delicious wine to keep them company. If this sounds interesting, Geneva is loaded with wineries from the lakeside Ventosa Vineyard to the rustic Ravines Wine Cellars. Always full of interesting conversations and friendly people, these outlets are perfect for a memorable vacation in Upstate New York.
Beacon
Beacon is an artist’s dream destination hidden in Dutchess County, New York. The town of 13,800 is overflowing with creativity which is prevalent no matter where you are. Whether it is a boutique shop full of handmade goods or an art gallery, artsy activities are abundant. When it comes to galleries, Dia Beacon and Hudson Beach Glass stand as beacons of artistic excellence. Dia Beacon, a monumental 160,000-square-foot exhibition space, showcases the Dia Art Foundation's extraordinary collection. Similarly, glasswork enthusiasts adore the intricate works at Hudson Beach Glass and can take home a piece or two from their inviting gift store. Most of these sites lie on Main Street, which boasts tons of cafes, boutiques, and outlets for a fun time in Beacon.
While in Beacon, stop by the Bannerman Castle, an abandoned military warehouse resting on a Hudson River island. The site is an iconic landmark, and people can get some amazing photos of the historic ruins. Several activities are available, such as walking tours of the castle, kayaking trips, and movie nights in the ruins. As the sun begins to set, head back in town to watch the downtown waterfall before heading to bed.
Lake Placid
Lake Placid is more than just a town; it is a reprieve of Upstate New York’s natural beauty. It was the host of the 1932 and 1980 Winter Olympic Games, which is a strong part of the town’s heritage. One can learn about these iconic events at one of the many Olympic sites here. For example, skiing slopes, a high-speed gondola, and bobsled runs from the time are open to guests who can reminisce in the Olympic vibe. Meanwhile, history buffs love the Lake Placid Olympic Museum which showcases dozens of photos, videos, and artifacts that tell the town’s stories.
Centered within the Adirondack Mountains, Lake Placid boasts various natural formations, from tall peaks to glistening lakes. Adventurers looking for an adrenaline rush should head out to Whiteface Mountain, one of the best ski destinations in the state. With over 80 trails running down the massive mountain, it is a world of fun cutting through the snow. If you’re visiting during the Fall, High Falls Gorge and Mirror Lake are must-visit locations. These areas transform during the cool season, with shades of yellow, red, and brown creating a mystical scene. Add on the waterfalls and hiking trails for an amazing outdoor vacation in New York.
Ithaca
Ithaca is a bustling college town on the southern shore of Cayuga Lake. Home to the Ivy League Cornell University and Ithaca College, there is an air of energy in this town. Filled with students from all over the world, eateries, stores, and bars are a great way to enjoy the vibe. Downtown Ithaca is a great place for this, with spots like Hawi, Alley Cat Cafe, and Ithaca Ale House. From enjoying a morning coffee to hitting some drinks with the locals, these outlets are full of vibrance. Even a stroll through downtown is full of, great photos, lots of shopping, and fun conversations.
Speaking of conversations with the locals, tourists can meet the town’s college crowd with a trip to Cornell University’s campus. Covering over 700 acres atop a hill near town, it offers stunning views of the streets and nearby Cayuga Lake. Inside the campus, plenty of historic landmarks such as Bailey Hall, Wing Hall, and Morrill Hall create a rustic vibe worthy of this Ivy League institution.
As you look down from the campus, Ithaca’s natural hotspots are sure to shine. For example, Cayuga Lake is a popular spot for both locals and tourists, with tons of ways to enjoy the reflective waters. Kayaking, sailing, hiking, and biking are just a few ways to have a blast here. Or, if you don’t mind heading out of town, Buttermilk Falls State Park is the epitome of outdoor beauty. Home to ten waterfalls, it seems straight out of a fantasy novel, with cascading water and verdant forests throughout.
Woodstock
Woodstock lies three hours from Ithaca, and is one of New York’s best cultural hubs. The town, with plenty of artists, musicians, and actors, gained fame for the 1969 Woodstock music festival (which did not take place here). To this end, it is a utopia for creativity, with art galleries, outdoor markets, and live music all around. Fans of art can check out galleries such as the Center for Photography at Woodstock or Elena Zang Gallery, each showcasing unique items. Or, opt for a performance instead at the Bearsville Theater. From indie acts to local musicals, creativity seeps through every corner of Woodstock.
If you’re lucky, you might be in town for one of the many festivals that bring in loads of artists and tourists from across the country. For example, the Woodstock Film Festival is a prestigious event with awards presented to various film categories. In the same way, the iconic Christmas Eve celebration in Tinker Street brings the whole town together. Kids receive toys, vendors sell treats, and Santa Claus freely roams for a delightful winter event.
While there is no end to the radiance in Woodstock, the town is also an abode of outdoor vibrance. All you need to do is walk south until you reach the Ashokan Reservoir with its glistening waters. Although the water system is kept safe by restricting most activities, boating and fishing are allowed with a permit. You can also head west instead to take in New York’s Catskill mountains.
Skaneateles
Skaneateles is the perfect place for people who want to sit back and relax. Astray from the hustle and bustle of urban cities, this town of 7,000 in Onondaga Country is a quaint retreat. Nestled right next to Skaneateles Lake, visitors can take advantage of the beautiful scenery abound. Just hop on a sailboat and you can spend the next few hours sailing open waters within verdant greenery. There are also designated sightseeing tours that offer sweeping views of the lake for an unforgettable sight.
Speaking of lakeside, Skaneateles is also known for its amazing food, especially when it comes to seafood. Popular areas like Genesee Street are full of great spots to eat like Blue Water Grill and Doug’s Fish Fry. Try out dishes like the seafood chowder and lobster bisque to give your taste buds a party. Wash it out with a drink from the LakeHouse Pub to get ready for some more fun in Skaneateles.
As you get back outside with newfound energy, Skaneateles’s history is sure to intrigue. the local historic society is a great way to learn about the past, telling the 200-year-old tale of the town. As you witness press clippings, boat displays, and even children’s toys, the echoes of a bygone era seem to be prevalent all around. Put this together with the array of boutique stores in town for a multi-faceted destination anyone will adore.
New Paltz
If you enjoyed the boutique stores of Skaneateles, New Paltz should be next on your list of unforgettable towns. This picture-perfect town is a world of fun, especially down the Main Street. Tourists enter a new world as they are surrounded by funky attractions and quirky outlets in this college town. Hotspots like Water Street Market liven up the environment with its open-air shopping concept. Here, one can purchase sculptures, jewelry, antiques, and more for the perfect souvenir.
Speaking of antiques, New Paltz is also home to an intriguing colonial past. People interested in this part of town can opt for Huguenot Street instead, which is a 10-acre National Historic Landmark District. Buildings here date back hundreds of years, such as the 1721 Jean Hasbrouk House and the 1717 Crispell Memorial French Church. Take a guided tour or adore the iconic architecture which will transport you to an era that has past.
Continue the historic architecture with a different angle at the Mohonk Mountain House, One of the most famous hotels in the region, this Victorian Castle Resort lies within the Hudson Valley. Thus, one can enjoy luxury rooms, a spa, delicious dining, and more within 40,000 acres of wildlife. The property itself also has various meadows and gardens offering a breath of fresh air in Upstate New York.
Sleepy Hollow
Sleepy Hollow is a mystical destination on the west bank of the Hudson River. The town offers a unique take on the typical waterside town. Instead of watersports, most people come here for the spooky history that follows. This is because Sleepy Hollow is famed for Washington Irving’s “The Legend of Sleepy Hollow,” an 1820 short story about the Headless Horsemen. Bolstered by the story, many places in the town are deemed to be ‘haunted,’ such as the Sleepy Hollow Cemetary. Here, one can experience true fear, as they walk by the gravestones of William Rockefeller, Walter Chrysler, and Washington Irving himself. The Headless Horseman Bridge and the Old Dutch Church of Sleepy Hollow are also famous for their paranormal activity. People have claimed to see the Headless Horseman, hear strange sounds, and feel a chill when in these locations.
While the town’s spooky past is the prime attraction, you don’t need to enter the world of the occult to have a blast. Instead, check out the non-haunted destinations, like the Kykuit Estate and Farmers Market. Historians rejoice at Kykuit Estate, which showcases a century of art, architecture, and stories. Meanwhile, the farmers market is a go-to spot for positive vibes, whether it is through fresh fruits or a local festival.
Upstate New York is a worthy destination for all kinds of visitors. No matter what you are into, there is something for everyone in these small towns. For example, adrenaline-seekers flock to the trails in Catskill while artists adore the creativity in Beacon. Moreover, each town has culture, heritage, and beauty in plentiful amounts. With so much to see and do, there are few places as unforgettable as Upstate New York.
