8 Adorable Small Towns in Upstate New York to Visit in 2024

There’s more to the state of New York than just New York City! Situated in the Adirondack Mountains, the Catskill Mountains, and the Appalachian Mountains, these small Upstate New York towns are adorable and gorgeous. From quirky locally-owned shopping districts to historic landmarks and stunning hiking trails, every town is worth checking out. For many, you don’t need to travel far outside bustling cities to step into what feels like a postcard. The locals are friendly, the food is amazing, and the sites are stunning. There may even be a castle or two worth discovering!

Watkins Glen

Watkins Glen is a sleepy town on the banks of Seneca Lake and is often referred to as the Heart of the Finger Lakes. The recently renovated downtown area hosts many quaint local shops cafes, and restaurants with scenic lake views. For nature lovers, there are plenty of local hiking trails that provide stunning views of the area.

The most notable park in the area is the Watkins Glen State Park. Lace up your hiking boots and travel deep into the gorge of this state park. You may even see a waterfall or two! This stunning park is home to 19 picturesque waterfalls, so get that camera ready! After a long day of hiking and sightseeing, make sure you unwind at Lakewood Vineyards with breathtaking views of Seneca Lake.

Lake George

Lake George is also known as the Queen of American Lakes, and is one of the cleanest lakes in the world! The stunning views of Lake George have been a top vacation spot for travelers for over 200 years. Head to Million Dollar Beach to curl up on the shores with a good book, or head to one of the many historical sites in the area. Head to Fort William Henry, the Chapman Museum, or the Bolton Historical Museum. For history buffs, there’s no shortage of things to see in Lake George!

There are also a few local parks situated along the lake to take a hike, unwind, or have a picnic. Head to Lake George Beach, or head outside of the town limits to Prospect Mountain. Prospect Moutain is a challenge but offers stunning views of the Adirondack Mountains.

Saratoga Springs

Saratoga Springs is a historical town in Upstate New York with something for everyone. If you are a history buff, head of one of the many local museums like the Saratoga Springs History Museum, or the enormous Saratoga Automobile Museum. Do a little shopping at the Saratoga Marketplace with tons of quirky and locally-owned shops and galleries, and grab lunch at a local cafe.

While the downtown area is bustling, Saratoga Springs is a great place to relax and unwind. Head to the Saratoga Spa State Park to relax in one of their natural mineral springs like the Victoria Mineral Pool and Peerless Mineral Pool. Soaking in the springs feels especially good after a long hike at Geyser Creek Trail!

Skaneateles

Skaneateles, aka the Jewel of the Finger Lakes, boasts one of the cleanest lakes in the country. Nestled at the tip of Skaneateles Lake, it’s a cozy lakeside down with so much to see and explore. The downtown area is a great place for shopping, boating, biking, and relaxing at one of its many beautiful vineyards. Spend the day exploring the local shops in the downtown area, then spend the evening at the breathtaking Anyela's Vineyards with a view of the lake.

Aside from its bustling downtown district, Skaneateles is surrounded by some of the most beautiful parks in the state. Hike the easy trail at Charlie Major Nature Trail, or admire the waterfall at Carpenter Falls. Situated a few hours out of Syracuse, it’s the perfect sleepy town without traveling too into the wilderness!

Cold Spring

Cold Spring is a cozy little town not too far north of New York City. Its historic downtown area is home to many quaint shops and cafes to keep you occupied all day. It’s on the National Register of Historic Places, feels like stepping back in time. Head to the Magazzino Italian Art Center, and spend the day shopping in the downtown district. While you’re here, however, you have to take a short trip to check out Bannerman Castle!

Outside of this quaint little town are plenty of parks and natural attractions that make Cold Spring unique. Situated north is the Hudson Highlands State Park. It offers many challenging and accessible trails that are perfect for the whole family. Nestled on over 6,000 acres of dense wooded forests and lakes, it’s the perfect spot for fishing, hiking, and adventure.

Sleepy Hollow

Sure, Sleepy Hollow is better known as one of the most haunted places in the world. With a rich history, stunning natural parks, and a quaint downtown area, it’s more than just a ghostly town. It may be haunted, but it’s listed as one of the safest cities in the United States! Be sure to check out the Headless Horseman statue and the Sleepy Hollow Cemetary in the downtown area while you stroll through the local shops and cafes. For a real treat, Kykuit (the Rockefeller Estate) is a stunning estate with over 40 rooms and scenic gardens to explore.

Outside of this historic downtown area is a plethora of lakeside parks along the Hudson River. Head to the Sleepy Hollow Lighthouse to snag a few photos, then take a walk at the Scenic Hudson RiverWalk Park at Tarrytown.

Catskill

The Catskills is so beautiful that it’s the home of four films and even works of art. It’s located along the Hudson River just south of Albany and offers breathtaking views of the Catskill Mountains, a rich history, and plenty to discover. The downtown area hosts unique locally-owned restaurants and cafes, and plenty of of shopping. Be sure to check out the Thomas Cole National Historic Site, and then catch some live music at The Avalon Lounge.

While Catskill has a thriving downtown area, it’s also a great place to kick back and relax. Dutchman's Landing Park, located on the Hudson River, is the ideal spot to launch a boat for a day on the water or set up a picnic river-side. For more adventure, check out The Slide Mountain Wilderness Area with easy to challenging trails and some of the most stunning views and waterfalls.

Woodstock

Looking for an area with a unique and bohemian vibe? Woodstock is located in Upstate New York and needs no introduction. It was the home of the Woodstock Festival in 1969, and today is a quirky and unique town with a proud history. The downtown area hosts cultural landmarks, like the stunning Olana State Historic Site, Sunfrost Farm, and the Holy Transfiguration Church. Catch a show at the Bearsville Theater, or just explore the quirky shops and cafes on Tinker Street.

For more scenic views, head south of town to the Ashokan Rail Trail- Woodstock Dike Trailhead situated on the banks of the Ashokan River in the Bluestone State Forest. It offered paved bike trails, challenging hiking trails, and fantastic water views. Or, head a little further south to the Onteora Lake Trailhead for a relaxing day on the water.

Escape From the Big City

You don’t need to travel far outside the big cities of New York to find peace and solitude. These adorable towns provide all the charm and character of the larger cities with a small-town vibe. Whether you want to relax on the lake, pack a fishing pole, or hike a challenging trail in the heart of the Adirondack Mountains, these cities are worth the drive. History buffs will fall in love with Lake George, and Sleepy Hollow proves to be much more than just a Halloween destination. With so much to offer, these adorable Upstate New York towns are great for the whole family.