Village Mall on Canada Street in Lake George, New York

9 Picturesque Small Towns in New York for a Weekend Retreat

New York is a beautiful state with mountain ranges, valleys, and water scenes straight out of a fairytale. Of course, New York City is the most popular and populous city in the United States. One could spend a lifetime exploring the Big Apple's five boroughs, sites, and attractions. However, once you get out of the city, New York boasts a ton of beautiful towns. Here are nine picturesque small towns for a weekend retreat. 


View east along East Main Street, Amenia, New York
View east along East Main Street, Amenia, New York, By Daniel Case - Own work, CC BY-SA 3.0, Wikimedia Commons

The small town of Amenia is a nature lover's dream come true. The name Amenia is derived from the Latin amoena for "pleasant to the eye" and was given that name by European settlers in the 1700s. Horse farms and hills are set against the backdrop of the Taconic Mountains. 

The Wethersfield Estate and Garden is a jaw-dropping 1,000-acre estate of natural and classical artistic beauty. Visitors are encouraged to tour the house, the trails, and the garden, the finest classical garden in the US. The Wassaic Project is a non-profit artist organization that provides education and residency for artists and can be found in the hamlet of Wassaic. The exhibits are located in Maxon Mills, a seven-story grain elevator, and should not be missed. Though only 85 miles north of NYC, the natural beauty of Amenia provides a bucolic retreat in the countryside.

High Falls

Buildings in the High Falls Historic District
Buildings in the High Falls Historic District

High Falls is a small hamlet in Ulster County and is named for the 150-foot waterfall in the Hudson Valley. Today, it is known as a hub for antiques and dining but it was once known for its canal. The town remembers this canal with the D&H Canal Museum, located in town and borders the former waterway.

Also in town is the Wired Gallery, a tasteful art gallery that showcases area artists and is a common stop for visitors. Of course, no trip to High Falls is complete without a hike to the waterfall that gave the name to the town. This is a premier town in the Hudson Valley that is just a short trip from New York City and is perfect for a weekend jaunt. 

Lake George

Canada Street in Lake George, New York
Canada Street in Lake George, New York, via OlegAlbinsky /

Lake George is a town located in the Adirondack region and is surrounded by old-growth forests. The area is a premier ski destination during the winter and hosts the annual Winter Carnival to celebrate the beauty of the region. The town is also steeped in history and is home to Fort William Henry, a British fort built in 1755. There is a museum, the Fort William Henry Museum, that highlights the history through reenactments and exhibits.

For a fun afternoon in town, visit the House of Frankenstein Wax Museum. This eclectic, and possibly haunted, museum is closed until April 2024 but is a must-see attraction. After a day on the slopes are getting the wits scared out of you at the wax museum, wind down at the Lake George Distilling Company, an artful distillery and tasting room that specializes in small batches using locally sourced ingredients.


Street view of Skaneateles
Street view of Skaneateles. Image credit PQX via Shutterstock.

Skaneateles is an Iroquois word meaning "long lake" and this picturesque town is named for the lake it borders. The lake is magnificently blue and stays that way because it is oligotrophic, which means the lake is low on nutrients so the algae stay away. The 16-mile-long lake is long enough to have a long community pier with boat slips and romantic gazebos.

This lakeside has a history dating back to the Revolutionary War when soldiers were awarded land grants. A few of the homes were also stops along the Underground Railroad. This information can be explored in detail at the Skaneateles Historical Society which is housed in a former creamery built in 1899. The best time to go is in August when the town hosts the Skaneateles Festival, a four-week lakeside music festival. 2024 promises to be even more special as it is the festival's 45th anniversary. 


Chatham Wine and Liquor vintage sign, Chatham, New York
Chatham Wine and Liquor vintage sign, Chatham, New York, via jonbilous -

Chatham is a small town in the Hudson Valley with a quintessential downtown and is known for its vibrant art scene. Once known as Groats Corner, Chatham is known for its sense of community, and this is evident in the downtown area. The 1811 Inn in Central Square is the town's oldest building while the public library, built in 1905 retains its original Tiffany window. 

The proudest feature of Chatham's downtown is the clock tower on Main Street. Built in 1872, it is still in working order and makes for a great photo backdrop. There is also an eclectic mix of comfort and fine-dining restaurants including Bimi's Cheese Shop. Walking through downtown is like taking a trip through Americana and a stop at the 40-year-old Chatham Book Store completes the experience.


Trumansburg, New York Main Street
Trumansburg, New York Main Street

Trumansburg, in Tompkins County, is a misspelling of the founder's name, Ebner Treman, and is located in the Finger Lakes region. The small village's two claims to fame are Taughannock Falls and the Rongovian Embassy, lovingly known as the "Rongo". The 3/4 mile Gorge Trail leads up to the 215 foot waterfall, the largest waterfall east of the Rockies.

Other points of interest are The Ulysses Historical Society Museum and several wineries including Idiot Brothers Cider. The Spa at Gothic Eves makes for a relaxing day after hiking to Taughanock Falls and before imbibing at a local microbrewery like Garett's. A unique stop is the Salmon Pottery Gallery and Studio where they host classes that teach visitors how to make pottery.

Penn Yan

Main street in Penn Yan, New York
Main street in Penn Yan, New York

Penn Yan is a small village that has one of the nation's oldest mills, The Birkett Mills, built in 1797. The unique name is derived from the words "Pennsylvania" and "Yankee", in honor of the town's founders in the 19th century. The town has an abundance of vineyards including the Fox Run, overlooking the Seneca River, and the Kekua Spring Vineyard.

The Penn Yan Diner is a throwback to the vintage diners and is a must-stop location for breakfast. After breakfast, a great way to spend the day is by hiking the Keuka Outlet Trail, which boasts an astounding 10,000-year-old history. Penn Yan is also home to a destination old-fashioned candy shop, the Keuka Candy Emporium. You can tap into your inner child and experience the candies, old-fashioned sodas, and old-fashioned ice cream from yesteryear. 


View of the Main Street in Narrowsburg, New York
View of the Main Street in Narrowsburg, New York

Narrowsburg is a small hamlet in Sullivan County with a population of less than 500. The town is located on the Delaware River and there are several hiking trails to explore like the 2.9 mile Tusten Mountain Trail that crosses a footbridge. The Fort Delaware Museum details the farming history of this important piece of agricultural land dating back to the 18th century.

The River Gallery on Main Street is a retail conglomerate created by two fashion experts that marries Asian and American antiques along with exhibits from local artists. The Blue Fox Motel is a rustic retreat that is perfect for a weekend getaway. It is located in a field where the Ten Mile River meets the Delaware River and is a perfect mix of city and country life. 

There's no doubt that New York, although known for its big cities, also is home to beautiful towns and hamlets. There is plenty to explore for the nature lover and the "townie" alike. From tremendous waterfalls and hiking trails in High Falls to the Old Fashioned candy shop in Penn Yan, New York has it all.

The Blue Fox Motel is an idyllic retreat for those looking to get away from the big city. There is also an abundance of art galleries, wineries, and historical markers in these towns. If you are looking for a small-town weekend getaway, it is hard to beat these nine towns.

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