29 Charming Small Towns in Upstate New York State + Hidden Gem Getaways

alexandria bay a small town in upstate new york

Family-owned businesses, farmers’ markets, and museums are just a few of the reasons why I love exploring small towns in my home state of New York. Just a drive or a bus/train ride away, I love leaving the busy energy of New York City behind me for the peaceful charm of small towns in Upstate New York. Whether you’re planning a snowy winter wonderland getaway or family summer vacation, here are our tops 29+ picks for the best upstate New York towns to choose from for your next trip.

Since New York State is vast and offers an array of beautiful experiences, we’ve categorized this list by region. From the Hudson Valley to the Adirondacks, here is all of the information you need on what to do, where to stay, and which small town to visit.

Getting Around Upstate New York

Getting around upstate New York can be tricky if you don’t own a car. But worry not, there are different ways to get around. From trains to buses to car rentals — here is how to visit a cute small town in upstate New York.

Trains to Small Towns in New York

The Metro-North and Amtrak are wonderful options to help you plan a getaway to upstate New York. You can easily plan your trips by taking one of their several train routes to a small town. Most New York towns with an Amtrak or Metro-North train station (like Cold Spring or Beacon) are walkable and offer an array of things to do. If you’d like to do things outside of a downtown area, you may be able to hire an Uber.

Buses to Small Towns in New York

There are different bus companies that can take you to several small towns around Upstate New York. Check Wanderu for different routes and bus companies. Here are just a few:

  • Trailways (New Paltz, Geneva, Buffalo, Lake Placid, Lake George, Kingston, Ithaca, Phoenicia, Woodstock, etc.)
  • Greyhound (Mostly to the bigger cities in New York)
  • Jitney (North Fork, Hamptons, and other parts of Long Island)

Walkability in Upstate New York

Unfortunately, we live in one of the most unwalkable countries in the world. But, there are several towns in New York State where you can still get around on foot. Charming towns like Skaneateles, Beacon and Hudson are perfectly walkable. However, if you’re looking to spend prolonged amounts of time without a car, it’s important to plan the logistics for things like grocery shopping and outdoor adventures.

Car Rental Road Trips in Upstate New York

Renting a car is, of course, the best way to get around in most of New York State outside of New York City. With a car, you can venture out of small towns to explore the best lakes and waterfalls in New York or drive to different nearby attractions in Upstate New York like gemstone mines and swimming holes — all on your own schedule. Consider a long-term rental to lower the daily rate and using a credit card like the Chase Sapphire which includes car rental insurance.

More of Our New York State Travel Guides

If you’re interested in exploring more of our beautiful state beyond small towns, here are some of our top New York travel guides to continue reading:

Charming Small Towns in Upstate New York

Please note: we realize that the exact definition of “upstate New York” varies depending on who you ask. New York is an enormous state that expands far beyond New York City and even touches 6 different state borders + the country of Canada. Because of this, there is a town for every traveler in our beautiful state but this also causes a lot of debate on what constitutes “upstate” or “up-the-state”? Even though NYC is less than 1% of the landmass of New York State, NYC accounts for about 44% of the state’s population. So, chances are that if you’re reading this you’re probably from NYC. Therefore, for the sake of brevity and simplicity, we’re following the New York City definition: which means everything “up-the-state” and above NYC. Which is what we love to do! Exploring away from the hustle and bustle of NYC living!

Can’t go too far north in New York state? Then consider these charming Long Island towns as well.


Looking for small towns with easy access to lakeside activities, waterfalls, hikes, and wine country? Then look no further than the Finger Lakes region in Upstate New York. Just four hours from New York City, this beautiful area offers so many things to do that we dedicated an entire guide to the Finger Lakes region for first-time travelers. Below are some of the cutest small towns you can base yourself out of during your Finger Lakes vacation.

1) Skaneateles, New York (Hidden Gem!)

Located on the crystal-clear shores of Skaneateles Lake, the town of Skaneateles is one of the best upstate NY towns to visit to meet friendly locals, grab delicious food, explore walkable streets, and shop at tons of boutiques. Skaneateles is truly an Upstate New York hidden gem and yet it’s just an hour away from major cities like Syracuse and Ithaca. It is one of my favorite places to stay in the Finger Lakes!

In Skaneateles, you can wake up to beautiful views of the lake by staying at a waterfront spa resort and later take a guided boat tour with dinner, or rent a personal watercraft. Skaneateles Lake is also famous in the region for having some of the clearest and cleanest water in the entire state of New York (pictured above).

There are a number of historic sites here too. You can view Hazelhurst, a beautiful yellow mansion on the lake. Or, see the James and Lydia Canning Fuller House (built in 1815), which was once a part of the Underground Railroad.

Ultimately, the Skaneateles Historic District is the most popular place to visit, as it encompasses the quaint and cozy downtown area (pictured above). After a day of strolling and shopping, grab dinner and a cocktail at Elephant and Dove (truly some of the tastiest food in the region with healthy options). For a relaxing stay, consider staying at Mirbeau Inn & Spa. And for a classic bed and breakfast, consider resting at Sherwood Inn, established in 1807.

2) Corning, New York

Corning, known as America’s Crystal City, boasts being one of the most fun small towns in New York for us museums nerds. That’s because Corning is home to two epic museums, one of them being the world’s largest glass museum. You may be thinking “glass…. who cares?” But once you enter the Corning Museum of Glass, you’ll understand the significance of glass in our history, art, and technology. You’ll likely want to dedicate at least half a day to this museum and its galleries, workshops, exhibitions, and much more.

A unique event in Corning each year is GlassFest, a local festival held in late May. GlassFest is a great way to experience Corning- through local music entertainment, local business promotions, and also a guided Arts Crawl through public artworks. GlassFest is held in Corning’s historic The Gaffer District, and you’ll want to take time to explore here.

If you love art, you can’t miss Corning’s Rockwell Museum. It is one of my favorite museums in the world. Although relatively small, the quality of the art and exhibitions were captivating; especially to me as an artist myself. Their collection of American art is also uniquely curated and includes a diverse representation of BIPOC American artists. Incredible!

Wonderful places to eat in Corning are easy to find, like Market Street Social, which offers seasonal outdoor dining around fire pits. And if you love chicken wings, stop by Nickels Pitt and order the garlic-buffalo-parmesan. There are also gorgeous boutique shops, a beautiful town square, and numerous art galleries in town.

3) Penn Yan, New York

Located right on Keuka Lake, Penn Yan is one of the most beautiful small towns in upstate New York for water sports. The village of Penn Yan has two distinct areas. First, with a noticeable old town feel, downtown Penn Yan has many shops and restaurants. Spend a summer morning in the down area, renting kayaks on the lake and getting lunch afterward.

The second section of village area, the general Penn Yan region, holds a number of fabulous wineries and also locally sourced restaurants. Follow the Keuka Lake Wine Trail to discover all that this beautiful region has to offer. You may be lucky enough to see an Amish horse-and-buggy gallop past you, since this area has been attracting scores of Amish families for decades.

Ice cream lovers, don’t miss out the Spotted Duck Creamery for some “farm-to-cone” duck egg custard! And if you love an easy walk through nature, consider the Keuka Lake Outlet Trail for a flat walk to see Seneca Mills Falls (pictured above).

4) Ithaca, New York

There is so much to see and do in Ithaca as it’s home to the prestigious universities of Ithaca College and Cornell University– making it one of the best places to live in upstate New York! The lively downtown area always offers a unique experience. The pedestrian-only Ithaca Commons, located in the heart of downtown, hosts events, festivals, year-round dining, and local street performances. This is a great place to meet friends or experience the feel of one of the most liberal towns in upstate NY. You’ll love experiencing the welcoming, progressive, and intellectual feel of Ithaca with its colorful murals and banners reminding us that “Black Lives Matter.”

Outside of downtown, you can visit the deep gorge of Robert Treman State Park, the shores of deep Cayuga Lake, and many beautiful waterfalls in the area. Be sure to bring along a camera to document your adventures- these locations are breathtaking. 

5) Watkins Glen, New York

One of the best upstate New York getaways – a trip to Watkins Glen will leave you wanting more of the beautiful Schuyler County outdoors. Just a 30-minute drive from Ithaca (listed above), the town of Watkins Glen is located at the foot of the majestic Seneca Lake and at the entrance of Watkins Glen State Park! Two for one. So you can literally walk from the downtown area of this town towards waterfalls. Coupled with the delicious restaurants in town (listed below) and the Seneca Lake Wine Trail, Watkins Glens makes for a perfect New York weekend getaway.

This town is one of the best launching pads for a plethora of activities to enjoy in the area. For instance:

In and around Watkins Glen’s you can also visit antique stores, boutiques, and souvenir shops.

6) Canandaigua, New York

Once a Seneca village, this town in upstate New York is steeped in history. Down to its Native American name- meaning “The Chosen Spot”- Canandaigua certainly is one of the most historically unique upstate New York getaways. Not only can you experience the waters of nearby Canandaigua Lake, but you can also check out boutiques, art galleries, and numerous important sites. To name a few:

  1. Sonnenberg Gardens and Mansion State Historic Park is located just blocks from Canandaigua’s downtown. The sites’ 50 acres sprawl with themed gardens, and a beautiful Victorian summer home.
  2.  The Granger Homestead and Carriage Museum, from 1816, was the home of the first Postmaster General. Now, it includes the largest collection of horse drawn vehicles. Take a tour or enjoy a Yoga on the Lawn event. 
  3. The Ontario County Historical Society Museum, where Susan B. Anthony was tried for daring to vote in 1872.

Should you visit in the winter, spend a day at the premier winter resort Bristol Mountain. Here, you can ski one of the highest verticals with a 1,200’ rise. For a classic B&B stay, check out The Bella Ella Bed and Breakfast.

7) Geneva, New York (Hidden Gem!)

The small town of Geneva, NY sits on a mostly flat area of land surrounded by farmland and rests against Seneca Lake. Plan to stay somewhere unique, like Vinifera Inn located inside Belhurst Castle (pictured above). Or, stay in one of the iconic Geneva Row Houses while exploring the downtown area. 

Want to spend an evening out in this upstate NY town? Catch a show at the Smith Opera House and see wonderful ballets, hear international music, or listen to poetry. Or, visit on a Friday. The first Friday of each month is Geneva Night Out, where local vendors celebrate art and culture of the area.

While in Geneva, don’t miss the unique dining experience at FLX Table – A “socially connected dinner party” where you gather around other strangers in a communal dining experience hosted by a chef and sommelier. Book your spots here ahead of time and they sell out quickly!

Geneva is also home to the prestigious Hobart and William Smith Colleges. So in the downtown area, you’ll find co-working spaces, cafes, restaurants, and even a welcome center.

8) Auburn, New York (Abolitionist History)

Another one of the best places to visit in upstate New York for meaningful history is Auburn, New York. Auburn sits on the north end of Owasco Lake. The town got its name from a beautiful poem, “Deserted Village” by Oliver Goldsmith.

While you visit Auburn, you must stop by Harriet Tubman’s house to pay homage to one of our greatest American heroines. After escaping enslavement, Tubman rescued 300 other enslaved Americans using a network of safe houses that reached this very region in upstate New York. This was all despite having suffered a traumatic head injury (while enslaved) which affected her health for the rest of her life. She was also the first recorded American woman to lead an armed expedition during the American Civil War. During the Combahee Ferry Raid, she helped liberate another 700 enslaved Americans! Ms. Tubman retired and was buried in Auburn, New York. Today, you can visit her home (pictured above) in Auburn. She is an icon of revolutionary courage and freedom.

While in Auburn, you can combine your visit to the Harriet Tubman National Historical Park with a hike along the Charlie Major Nature Trail. Finish your trip to Auburn by visiting the downtown area, full of wonderful shops, art, and craft breweries. 

9) Aurora, New York

Aurora, once a short stop on an upstate New York road trip to elsewhere, is now one of our favorite cute towns in upstate NY. What changed? The creator of the American Girl brand once attended school at nearby Wells College. Years later, she returned and began to revitalize and restore the town, giving us the lovely Aurora, NY we have today. Thus, many buildings in the town are on the National Register of Historic Places. For instance, the Inns of Aurora, which was once a stop of the Wells Fargo Express and is now a premier resort (pictured above).

Additionally, Aurora is a sweet town to visit for pottery lovers. MacKenzie-Childs‘ gorgeous ceramics are hand-made here. So you can shop for MacKenzie-Childs ceramics here and/or explore their pottery campus and farmhouse. 


10) Troy, New York

Located just outside of Albany, Troy was once the 4th richest town in the United States due to its bustling textile industry. Today, this small town-like city in upstate New York is working to reinvent itself as a diverse community for artists, students, and young entrepreneurs. You can see the growing shifts in the downtown area where family-owned restaurants, bars, cafes, and shops are popping up along beautiful tree-lined streets. Visitors can enjoy farm-to-table dining at many restaurants like New World Bistro Bar or Healthy On Lark. There are also plenty of co-working spaces to choose from, should you decide to stay here longer.

Arguably one of the best farmer’s markets in New York, Troy’s Waterfront Farmers Market (in the summertime) is a must-see. Shop local boutiques, sample delightful culinary offerings, and enjoy a lively environment along the waters of the Hudson River.

11) Saratoga Springs, New York

While the Saratoga Race Course and the National Museum of Racing and Hall of Fame remain some of the most popular things to do in this college town in upstate New York, Saratoga Springs also has a number of other wonderful attractions you’ll love. 

Located on Saratoga Lake, visitors can charter a cruise at the Adirondack Cruise and Charter Company, or take part in a floating classroom experience. For a more relaxing experience, visit Saratoga Spa State Park (pictured above) with historic buildings, sprawling grounds, and mineral spa baths that will leave you rested and refreshed. Don’t forget to taste the naturally effervescent and nutritious spring water!

Art lovers, stop at the Saratoga Arts Center for a taste of the local art scene. 

For foodies who love flavorful cuisine and a good cocktail, grabbing dinner Boca Bistro is a must! It is one of the best and tastiest restaurants in Upstate New York. Everything we ordered there was delicious including the cocktails. Finally, Caffe Lena is a cozy hidden gem in an “intimate setting steeped in history” – catch live music or take music classes here, at the longest continuously operating folk music venue in the United States. 

Spend your nights at the luxurious Adelphi Hotel which will take you back in time with its art deco-esque decor. You can enjoy the hotel’s spa here as well, and on-site restaurants (pictured above).


12) Woodstock, New York

The small town of Woodstock became famous for its namesake music festival which actually took place in Bethel, NY. However, Woodstock still holds its cool hippie reputation to this day. The food, music, and arts scene here is still vibrant. For live music, check out the rustic barn at Levon Helms Studio. For art lovers, don’t miss the works of local artisans at one of Woodstock’s many art galleries. Foodies, be sure to make room for all of the delicious eateries in town such as Oriole 9 and Sweet Dreams Organic Ice Cream.

You can fulfill your adventurous side here, too. Take the 40-minute drive to Peekamoose Blue Hole, swim at Fawn’s Leap Waterfall, or go hiking at Kaaterskills Fall (pictured above).

13) Phoenicia, New York

Just 22 minutes from Woodstock is the sleepy town of Phoenicia. There is a quiet stillness, a green fragrance, and lush vibrance that this town exudes. Phoenicia is the perfect town for relaxation and the outdoors. Here are a few things you can’t miss in Phoenicia:

  • Esopus Creek – The small town of Phoenicia is located along the Esopus Creek River which offers visitors opportunities for tubing or rafting.
  • Rail Explorers (Pictured above) – The locals may make fun of you for this, but so what?! This fun experience allows visitors to peddle their way over a train track that runs along a precipice overlooking stunning views of the Catskills and Esopus Creek.
  • Phoenicia Diner – A classic spot for travelers to pop in for an all American plate of food between excursions.
  • o hiking along the many trails of Phoenicia.
  • Phoenicia International Festival of the Voice – A five day festival of live music entertainment.
  • Shopping at special stores, like Tender Land Home, or Phoenicia Arts and Antiques.
  • Stay in cool, unusual settings, like mountainside tent glamping, a cozy lodge in the country, or the gorgeous and rustic Deer Mountain Inn.

14) Saugerties, New York

Located along the Hudson River and the Esopus Crek, the small town of Saugerties offers both easy access to the outdoors and small town charm.

Catch a delicious breakfast at Bluestone Roasting Co, pick your own blueberries at nearby Greig Farm, and stay at immersive Villa at Saugerties. With its quiet streets, iconic brick lighthouse, and also nearby wooded Falling Waters Preserve, you’ll want to explore the entire weekend away. 

If you love the outdoors, head over to Saugerties Village Beach (walking distance from downtown) and stop by I Paddle New York to rent a kayak or go on a kayaking tour down the peaceful Esopus Creek. Just a ten-minute ride from downtown Saugerties is Tullin Ranch (pictured above) where you can ride horses.

15) Kingston, New York

The first capital of New York State, Kingston, offers several things to do for a quaint day trip. As one of the battlegrounds during the American Revolution, much of Kingston was burned down by the British. But still, remnants of Dutch and colonial influence can be found well-preserved especially in its historic center.

Considered a small city, Kingston has three distinct neighborhoods; the Uptown Stockade Area, Midtown Area, and Downtown Waterfront Area, or Rondout. If you can only pick one, I recommend strolling around uptown. Here you can head straight to Rough Draft Bar & Books located in an old colonial-style building on a historic street.

If you can spend more time, visit the waterfront, stop by the Kingston Farmers Market, and stay at the beautiful Forsyth B&B.

16) New Paltz, New York

New Paltz is special. As soon as you enter the town you’ll see a small Dominican restaurant at the foot of the main street. That alone wins major points for the diverse cuisine offered in this small artistic college town. Stroll down Main Street in the downtown area of New Paltz to see more different restaurants, shops, and art galleries such as the DM Weil Art Gallery Unison Art Center.

New Paltz is also at the foot of so many day hikes from NYC to choose from such as Artist’s Rock (pictured above). New Paltz is not only home to fabulous destinations like the Mohonk Mountain House, and surrounding Minnewaska State Park Preserve, but also:

  • Huguenot Street, where you can feel the French influence of the area surround you.
  • Fabulous Robibero Family Vineyards, nestled into the charming landscape, and
  • Buttermilk Falls Inn and Spa, a working farm, spa, and luxurious hotel- the perfect place to end a fantastic day.
  • Go glamping with Tentrr Signature.


17) Cold Spring, New York

Probably the easiest small-town getaway from NYC is Cold Spring. Just a 90-minute train ride from Grand Central on the Metro-North brings you directly into the town. Here, you can start your day with breakfast at delicious Hudson Hil’s Cafe. Spend your day adventuring by hiking Breakneck Ridge, one of the hardest hikes in the area or kayaking with Hudson River Expeditions. Alternatively, explore the art at Magazzino Italian Art Museum, go shopping for antiques, and admire the notable buildings around Cold Spring. Finally, end your day at the Pig Hill Inn, resting right on the cozy main street. 

18) Hudson, New York

Hudson, New York is often regarded as the Brooklyn of Upstate New York.

For many, it’s a once historic port town turned expensively hip and a little snobby (like pockets of gentrified Williamsburg). And for others, it’s a sweet respite from city living just a two-hour train ride from NYC. You decide where you fall along that line!

While visiting Hudson, visitors can stroll through the downtown restaurant scene on Warren Street, Hudson’s main street. Stop at Hudson Wine Merchants for wine tasting, and WM Farmer and Sons for steaks and seafood. You’ll want your camera for capturing the sights of unique 100-year-old buildings as you stroll. 

Hudson also offers many museums and art galleries, like:

Don’t miss taking a ferry boat tour to the Hudson/Athens Lighthouse. In the summertime, the experience is picturesque, especially as the sun sets in the summertime. Afterwards, remain immersed in the artistic ambience by staying at the Wm. Farmer & Sons, Tiger House or The Maker Hotel (pictured above).

19) Rhinebeck, New York

Charming Rhinebeck also boasts a cultural center, with art galleries, performing arts, unique architecture, and more. In addition, Rhinebeck offers epic outdoor recreation in popular hiking and biking trails, interesting shops, and great places to dine, like Bia. All this, set against beautiful views of the Catskill Mountains, will make you love visiting this small town in upstate New York. 

Fun fact: Paul Rudd co-owns the candy shop Samuel’s Sweet Shop located in the downtown area.

20) Beacon, New York

Located in the Hudson Highlands, Beacon is another super easy small town to visit from NYC by train. The Metro-North leaves you at the foot of the downtown area; where you can do several different things within walking distance making it the perfect day trip from NYC.

Beacon is known for its contemporary art scene and craft beers. Check out the must-see art museum Dia: Beacon (book your tickets ahead of time) and the Hudson Beach Glass glassblowing studio and museum. Then, visit one of the many craft breweries nearby, like Two Way Brewing Company and Hudson Valley Brewery. Finally, finish out your day with dinner at the Roundhouse.

If you visit for a New York City getaway weekend, be sure to book a room with mountain views at the Roundhouse. When you’re not enjoying the view (pictured above), stroll the cute main street and enjoy the distinctive art murals of Beacon. Stop into one of the many local restaurants and boutique shops. Finally, stop by the local flea market.

Enjoying the beauty of the area is simple here, too. A short drive will take you to Hudson Highlands State Park, where you can catch a glimpse of some gorgeous waterfalls on different hiking trails. Similarly, kayak to Pollepel Island to view the breathtaking Bannerman Castle.


21) Paul Smiths, New York

Looking for an outdoor adventure? Look no further than this small upstate NY town. Nestled deep in the Adirondacks, Paul Smiths is close to the Lower St. Regis Lake, St. Regis Mountain, and Seneca Lake. Perfect for nature lovers! The town is named for the Paul Smith’s Hotel, built-in 1859 and one of the first wilderness resorts in the Adirondacks. 

Today, you can find many hotels, cabins, and cottages that are perfect for your Adirondack adventure. For instance, stay at White Pine Camp (pictured above)- former summer White House for President Calvin Coolidge, the Saranac Waterfront Lodge, or Camp Hatteras, a private vacation rental on 33 acres of quiet land. Any one of these stays offers the best access to outdoor recreation. 

During the winter months, don’t miss out on snowshoeing and cross-country skiing down the fluffy trails within the Visitor Interpretive Center (VIC). Consider spending the night glamping in the forest (pictured above).

22) Lake Clear, New York

Lake Clear is one of the smallest upstate NY towns with a population of only 523 people. This tiny town was once a bustling tourist area. Today, Lake Clear is still devoted to its guests, though in a much more peaceful setting. One of the town’s major draws is its proximity to the St. Regis Canoe Area. Paddlers of all levels love to cruise down its serene waters. In addition, this is a fishing paradise for anglers.

Our favorite place to stay in Lake Clear is Lake Clear Lodge and Retreat (pictured above). This retreat has been dedicated to wellness for generations and continues to offer special experiences surrounding luxury and nourishment, rejuvenation and discovery. Artisan lodgings are nestled into 25 acres of “Healing Woods”. In addition, the Lodge has Old World Food Experiences, including Adirondack Alps Cuisine, and a 1920s speakeasy. Lake Clear Lodge also provide free cross country skiing and snowshoeing.

After a time enjoying breathtaking mountain-lake sunsets, you should leave Lake Clear feeling completely refreshed. 

23) Lake George, New York

Lake George is a haven for hiking, rafting, and ice cream. During your stay, be sure to experience hikes like Prospect Mountain where you can see 100 miles away. Or, whitewater raft the Hudson River and Sacandaga Rivers. Finally, treat your sweet tooth along the NY Ice Cream Trail, which stretches from Lake George to Lake Placid and back. 

Finally, Lake George and the surrounding smaller towns have plenty of wonderful places to stay, like:

Wherever you chose to stay, you’ll love being immersed in the Adirondacks. 

24) Saranac Lake, New York

Saranac Lake is a hidden gem region in the Adirondacks, located just a 15-minute drive from Lake Placid. Its location makes it the perfect destination to add to your Adirondacks itinerary. Here you can enjoy several hikes, lake excursions, go fishing, boating, cycling, paddling, and much more.

In the winter, this area turns into a blissful winter wonderland where the powdery snow piles up several feet in the area. In the winter you can walk on the frozen lake, go ice fishing, snowshoeing, cross country skiing, and most popularly? Snowmobiling at Charlie’s Inn!

For delicious eats, grab a bite at The 1892 Bar & Grille and Charlie’s Inn.

Additionally, the village has a vibrant art scene, including murals, sculptures, and Third Thursday Art Walks. The Adirondack Artists Guild Gallery is a great stop during your visit. Here, you can view the works of Sandra Hildreth, who captures the landscape of the Adirondacks. 

For a cozy accommodation, check out the aforementioned Lake Clear Lodge & Retreat (12 minute drive away) for the perfect winter getaway filled with dinners, horse-drawn sleds, and speakeasy experiences.

25) Lake Placid, New York

On the hunt for fresh mountain air and majestic views? Lake Placid and the surrounding area has 2,000 miles of marked hiking trails in the Adirondack Mountains. Additionally, the region boasts 46 High Peaks, many of which are well over 4,000 feet. Some of these trails include climbable fire towers that offer a spectacular view from the top. This view is even better in the fall, so be sure to check the foliage report. If you’d like to explore this region for 1-2 hours, we suggest Balanced Rocks. Or, looking for a longer excursion? Hike to Lake Tear of the Clouds, the source of the Hudson River. 

Lake Placid was once an Olympic site, so part of the culture surrounds winter sports. You can try out a toboggan chute, or the Lake Placid Bobsled Experience. You can also catch live luge and bobsled/skeleton events each winter. At the end of your day, enjoy one of the many local farm-to-table options for dinner. Don’t forget to try snowboarding or skiing at Whiteface Mountain. If you’re new to winter sports, check out Casade Ski Center for cross country skiing and snoeshowing.

Finally, rest your head at Warner’s Camp– a renovated 1800’s guesthouse. Or, stay at the Haus on Mirror Lake, with a rustic yet modern vibe.  For a cocktail with lakeside views, go to the Mirror Lake Inn, a luxurious mountain lodge and restaurant with views of the lake and High Peaks.


26) Alexandria Bay, New York

One of the best places to visit in upstate New York, Alexandria Bay is a picturesque vacation destination. In the heart of the 1000 Islands, you’ll love the maritime feel of this upstate New York small town. While visiting Alexandria Bay, visit the 120-room Boldt Castle and Yacht House, take a boat tour, or stop into the Cornwall Brothers Museum and Store

Of course, you’ll want to stay near the water. So, wrap up a day of fun at Ledges Resort and Marina, where your view will include Boldt Castle, a lighthouse, beautiful grounds, and breathtaking sunsets. 


27) Oswego, New York

Oswego is located on the coast of Lake Ontario and is home to some of the most beautiful sunsets in the world. Due to it being home to SUNY Oswego, the historic downtown area also offers different bars and restaurants to choose from. In the summer, Harborfest is a four-day festival that brings over 75,000 visitors. During the festival, you can see major music performances and fireworks. And in the Spring of every year, the famous Bridge Street Run takes place. This is a massive bar crawl throughout the town where locals, college students, and visitors come together for one big outdoor party.

For outdoor lovers, don’t miss the Chimney Bluffs State Park and Salmon River Falls — one of the most beautiful waterfalls in New York.

Oswego also has a number of superb historical sites and museums. First, the Safe Haven Museum was once home to the only World War II refugee shelter in the US. Next, the Richardson-Bates House Museum showcases fascinating Victorian architecture. Additionally, Riverside Artisans showcases many local artworks. For those interested in American history, there are a number of other wonderful museums here well worth the trip.

28) Cooperstown, New York

Tucked against a tree-filled backdrop, Cooperstown’s downtown area is cozy and quaint. Within walking distance are a lakefront park, local boutiques, and restaurants. Here are just some of the many attractions this interesting town has to offer:

National Baseball Hall of Fame: Most famously, Cooperstown’s National Baseball Hall of Fame and Museum boasts 300,000 visitors every year. Visitors enjoy art, photography, historical artifacts, and stories celebrating the rich history of baseball. Don’t miss the Babe Ruth exhibit, or “Diamond Dreams”, focused on the women who contributed to the sport. Another exhibit, Viva Baseball, honors the influence of Latino (including Dominican) players in baseball’s history and today.

Otsego Lake: Otsego Lake lies at the north end of town in Glimmerglass State Park. Take a boat tour, or follow winding paths to stunning views of the lake. Or, hike Sleeping Lion trial to Hyde Hall Mansion museum, which overlooks Otsego Lake.

Farmer’s Museum: The Farmer’s Museum honors the traditions of rural upstate New York. They hold traditional events, like maple sugaring Sundays, livestock shows, and a harvest festival. At Christmas, horse-drawn wagons pull guests through the snowy grounds for a Candlelight Evening. The night is complete with a complimentary wassail and local ciders enjoyed around a bonfire. 

Fenimore Art Museum: The Fenimore Art Museum includes many important permanent collections. These include the Thaw Collection of American Indian Art, a Folk Art exhibition, an exhibition of American Fine Art, and “Coopers of Cooperstown”, which commemorates the literary tradition of Cooperstown’s founding members

29) Ellicottville, New York

The small town of Ellicottville in Western New York is known for its ski resorts, Griffis Sculpture Park, Sky High Adventure Park, and unique spas. The village also boasts 24 shops, 23 bars and restaurants, and a dozen special events throughout the year.

Be sure to stop into Winery of Ellicottville and taste their Bubbly Riesling, or Hideous Plaid Hard Apple Cider, made with New York State Apples. The apple cider is particularly refreshing after an autumn day catching amazing views of fall foliage. 

These small towns in upstate New York have it all; epic outdoor adventure, quiet spa afternoons, lively local evenings, and more. Come experience all that New York state has to offer! 

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6 thoughts on “29 Charming Small Towns in Upstate New York State + Hidden Gem Getaways

  1. Robert Dawley says:

    All good places to visit. However referring to them all as “Up state” shows your Big city arrogance towards the parts of the state outside your city borders. There is The Capitol District, the Adirondacks, Central, Western, and Finger Lakes areas. I miss the Southern Tier myself as it borders Pennsylvania and seems like its own country.
    To refer to all these individual areas as “Up State” shows how little you know or care.

    • Isabelle says:

      Hi Robert! Thanks for reading our blog. As I mentioned at the beginning of this article, for the sake of brevity, we referred to everything north of NYC and Long Island as Upstate New York (as in literally up the state) and then broke it down by the name of each region. Every region you mentioned, we literally added to the subtitles in this article when we broke it down by area. There is no need to be rude and name-calling NYC folks as having “big city arrogance” because we can’t list the name of every region on the main title which has limited space.

      Please be respectful on this platform. Contrary to your statement, this post was made out of the deep love and joy we have for upstate NY! I have gone to college in upstate, lived upstate for many years, rock the 315 area code, and regularly head back up throughout the year. We have a lot of love for it. Our state is enormous and offers incredible wonders from cities to waterfalls. Have a blessed day. Wishing you lots of healing!

  2. Patrick Parietti says:

    I liked the article. I live in Nyack, New York. Piermont is also charming. There are a lot of towns in the Catskills, Hunter, Tannersville. I am hoping to explore more in the Adirondacks. I used to do trail races in the Catskills. New Paltz is nice. I went to College at Oswego. There is a really cool farmstead in Rockland called the Orchards of Conklin.

    • Isabelle says:

      Thank you, Patrick! I haven’t been back to Piermont in so long, How is it these days? I love Tannersville! These are great reminders. Doesn’t Oswego have some of the best sunsets in the world? Noted on Orchards of Conklin, I will add that to my bucket list. Much appreciated 🙂

  3. Susan says:

    I am in my late 60’s and grew up on a multi generational/extended family dairy farm in the “Leatherstocking Region” (near Morrisville and Madison), with most of my relatives also farming in the area. Also known as Central NY. I have considered myself to b from upstate all my life. (As in Upstate Medical Center, etc). It’s still one of the undiscovered beautiful places in America.

    • Isabelle says:

      Hi Susan, You nailed. Upstate NY really is one of the undiscovered beautiful places in the USA. FULL of natural hidden gems. We are SO lucky!

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