Skaneateles, New York: Pier and luxury boats docked in the Skaneateles Lake, via PQK /

The Most Picturesque Small Towns in Upstate New York

Whether you're on a road trip across the Empire Staten or looking to unwind in a quiet town and enjoy nature, each upstate town's beauty is unreplicable. The small towns are the soul of New York, reflecting that the Empire State is more than just the Big Apple to take a bite of; it also has seafood, farm-to-table, and the best wines of the Finger Lakes region. Skaneateles is upbeat and upscale, with one of the cleanest lakes in the US, colonial inns, and stunning fall foliage, while Westport is a place of Adirondack Coast charm and adventure.

Catsill is an underrated town within the eponymous range, and Canandaigua is "the Chosen Spot," while Amsterdam sprinkles charms along the Mohawk River with a rich heritage replete with historical landmarks and authentic foods. As the prettiest in the stunning Thousand Islands area, Alexandria Bay is home to a castle on Heart Island, a place of breathtaking natural beauty on the sparkling St. Lawrence River.

Alexandria Bay

The view of waterfront homes in Alexandria Bay surrounded by striking fall foliage along St Lawrence River
The view of waterfront homes in Alexandria Bay surrounded by striking fall foliage along St Lawrence River, via Khairil Azhar Junos /

This small island town of under 1,000 tops the list as the prettiest in the stunning Thousand Islands area, shared between Canada and the US. While definitely part of the "Empire," you will feel a world apart in Alexandria Bay, thanks to its unique geographical features. Nestled along the sparkling St. Lawrence River, it is a paradise for boaters, with marinas and fishing charters, as well as rentals in town to navigate on your own. From golf to the fully digital Bay Drive-In Theatre just inland with a retro cafe, the riverfront Scenic View Park offers a seasonal swimming beach, a playground, and a picnic pavilion. Steps away, Uncle Sam Boat Tours is a fun and insightful way to explore the river.

While prowling for nearby eateries like Riley's by the River, don't miss the Church of St. Lawrence, a serene sight, while the Cornwall Brothers Store Museum, in a circa 1866 stone building, highlights the lifestyle, early trade, and commerce of the local settlers. Strolling along the coastline with a cone from Lil' River Fudge Co., you've caught sight of the picture-perfect Heart Island, Alexandria's own most-popular attraction. Visitors can enjoy boat access to the magnificent Boldt Castle on the 5-acre island, open for tours with its 120 rooms, formal gardens, and grounds to take in the view of the imposing stone castle, built in early 1900 in a European chateau style for a wealthy New Yorker.


Bridge in Amsterdam, New York
Bridge in Amsterdam, New York

The Montgomery County of Amsterdam is a picturesque slice of unique upstate New York history. Flanking the north and south banks of the Mohawk River, Mohawk tribes have long lived along the river named after them. The Dutch from Albany and Schenectady settled around 1710 and called the region Veeders Mills (or Veedersburg) after one of them, Albert Veeder, an early mill owner. Visitors can hunt around for early vestiges along the South Chactacunga Creek flowing into it from the west and views of the small Pilgrimage Island near the larger Davey Island. The walkable town of just over 18,000 residents and just 6.26 square miles packs a punch in attractions right from the train station, like Rockn J Flea & Antiques.

Next-door, the circa 1774 Guy Park House reflects the popular Georgian architectural style of the era. Starting the day at Rosito's Bakery, Shuttleworth Park is a popular local hangout. Visitors can enjoy river views from Front Street, Riverlink Park, or the spectacular Mohawk Valley Gateway Overlook Pedestrian Bridge with scenic sculptures by Dimitar Lukanov and historic plaques. The Saint Stanislaus Roman Catholic Church Complex offers more local culture and heritage on a stroll around its several church structures built in the late 1800s, an important bridge to the past. Cross the town bridge for authentic Italian fare at Lorenzo's Southside, or float under it from the boat launch with "Amsterdam" written across.


Main Street in downtown Canandaigua, New York.
Main Street in downtown Canandaigua, New York. Editorial credit: Ritu Manoj Jethani /

Just 25 miles southeast of Rochester, “The Chosen Spot,” according to the Native American translation of its name, Canandaigua is indeed a heart-wrenchingly picturesque town on the northernmost banks of the epynomous lake. Steeped in nature and illustrious history ever since, visitors can experience colonial life at Granger Homestead and Carriage Museum Grand, an 1800s mansion with expansive grounds, horse-drawn carriages, and sleigh rides in the winter. Home to the 1887 Queen Anne mansion and exotic flora formal gardens, Sonnenberg Gardens & Mansion State Historic Park is an unmissable attraction this summer for tours and strolls along its 50-acre grounds with arboretum.

The Canandaigua Lake offers a stunning backdrop to rest and relax, or while swimming, boating, or fishing, steps away from locally owned shops, galleries, and restaurants. If you're craving fast food after adventures, feel good about keeping it local at Tom Wahl's Canandaigua, established in 1955, to indulge in hamburgers and fries or a frosted mug of handcrafted root beer on a hot day. Grab it to go for a lakeside stroll at Kershaw Park, with a landscaped beach, a public dock, pavilions, and the gazebo. Home to the Land of Legends Raceway for relevant fans and accommodations to match any group and style, Roseland Wake Park attracts pros and families to try wakeboarding on a lake featuring a 5-tower cable system and a 2-tower training cable system.


Downtown Catskill, New York.
Downtown Catskill, New York.

Proudly christened after the spectacular upstate New York mountain range, Catskill is an underrated town in upstate New York along the picturesque banks of the Hudson River. Make Dutchman's Landing Park, Riverfront, your first stop with views from picnic tables, as well as grills, boat launches, and a playground for another visit. With Catskill Creek through the heart and Mawignack Preserve on the outskirts, there's a slice of the outdoors for every taste. The storefronts along two main streets on either side of the river give off distinct Victorian vibes that make Catskill a picture-perfect example of a historic river town.

Filled with an eclectic variety of eateries and boutiques, don't miss Cone E Island Ice Cream on a warm summer evening stroll creekside next to Bridge Street Theater. Otherwise, make it across the Rip Van Winkle Bridge to the Avalon Lounge, a live music venue, or Catskill Chocolate Co. The riverfront Thomas Cole National Historic Site on Spring Street, once home to the artist-founder and his famous 19th-century Hudson River School of Art, features period landscape paintings and mountain views at the doorstep. Home to just over 11,000, Catskill stays virtually crowfdless to find peace in a serene natural embrace.


Skaneateles Lake in Skaneateles, New York.
Skaneateles Lake in Skaneateles, New York.

Nestled on the shores of Skaneateles Lake, this thriving residential and business community, full of neighborly vibes, is Oprah's favorite getaway. With occasional celebrity sightings, it welcomes tens of thousands of regular visitors along one of the cleanest lakes in the country. Considered the jewel of the Finger Lakes region and Iroquois for "long lake," it is a place of extraordinary beauty, while the quaint town offers a generous dose of the Finger Lakes region's luxury and hospitality through affluent shops and stunning restaurants. From a slew of charming bed and breakfasts to pristine colonial inns, every season is picturesque with saturated natural colors. The historic downtown delights the eye and taste buds with culinary adventures, high-end fashions, galleries with original art, home decor, and special antiques.

From lakeside pursuits like swimming and boating to entertainment in the summer, the harvest season promises wine tasting, leaf peeping, and apple picking, while a winter escape imbues you with a wonderland feel straight from the old Christmas tale starting from Thanksgiving weekend. The fresh-faced nature in spring attracts crowdless strolls along the lake, the 32-mile bicycle excursion, or Clift Park, which gets busy on Fridays in July with its free concerts, while the pampering at Mirbeau Inn & Spa is a taste of what this town delivers for all senses. Take it up a notch for a breathtaking top-down perspective of Skaneateles and surrounding areas via an aerial adventure in a hot air balloon, while a Mid-Lakes Navigation vessel at sunset over cocktails is a picturesque memory to return to from your work desk.


Lake Champlain's shores in Westport, New York.
Lake Champlain's shores in Westport, New York.

Nestled on the Adirondack Coast, in between the mountains and the boundary with Vermont across Lake Champlain to the east, life in Westport, an Essex County gem, is picturesque. As the inventor of the Adirondack chair, the easy-going town offers easy interstate access or to its own Amtrak station, where you can feel the mountains breathe upon you, mixing in the exquisite yet down-to-earth vibes of rural charm. The pretty variety of landscapes is a beacon for water sport lovers and mountaineers, but also for those who enjoy the arts, special events, and farm-to-table food.

From Westport Golf to the hilltop Ballard Park against pretty lake views, good coffee and fine lakeside will get you in between. Starting the day at JAMBS on Main, visitors can enjoy a marina and boat launch to explore the scenic North West Bay and beyond, and dine mountaineer style at the Gables Inn Mountain Dog Restaurant & Pub. The Lee Park Trail ends at Hoisington Brook Cascade, a little fall under a stone bridge, while the Coon Mountain Hiking Trailhead, the Art Farm Trail, the Long Valley Trail, and the Field and Forest Trail are all within ten minutes.

Upstate New York is a generally down-to-earth region with rustic and charming towns in between sparkling lakes and mountain ranges. Offering an easy escape from NYC, often via Amtrak, it is a naturally diverse slice of the state to enjoy in your favorite way, from yoga retreats to camping, hiking, mountaineering, and lakeside pursuits.

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