The Best Small Towns in New York for a Weekend Retreat
New York is one of the oldest states in the U.S., and its longstanding and fascinating history is only matched by its natural wonders, exemplified by its pristine forests, lakes, and mountain ranges. Although the famed New York City has none of these things (besides a longstanding history), the state is full of dozens of much smaller communities that are just as worth checking out, particularly if you're simply looking for a relaxing weekend escape.
Check out these 11 small towns in New York and see if any of them can suit your next excursion this weekend.
Beacon
Located along the fast-flowing Hudson River, Beacon is a lively arts town, attracting visitors with its creative spirit and inspiring riverside setting.
The town’s crown jewel may very well be Dia Beacon, a massive contemporary art museum housed in a former Nabisco box-printing factory; a unique combination of New York's industrial past and modern cultural importance. Dia’s collection features large-scale installations and works by notable 20th-century artists, making it one of the region’s top art destinations.
Main Street in Beacon is the place to go if you'd like to indulge in craft breweries, like the Hudson Valley Brewery, and unique dining options, from farm-to-table eateries to artisanal bakeries.
Along the nearby waterfront, the Beacon Sloop Club is a unique attraction that provides visitors with tours on the Clearwater, a historic sloop designed to raise awareness of the Hudson’s environmental history.
For a true outdoor adventure, Mount Beacon sits a short drive away and contains a moderately challenging hike to a summit with sweeping views of the Hudson Valley.
Windham
Windham is a scenic village in the northern Catskills, a wonderful mountain range near New York City that is renowned for its abundance of outdoor activities and awe-inspiring natural beauty. Known as the "Gem of the Catskills," Windham is home to attractions like Windham Mountain, a popular destination for skiing and snowboarding in the winter while offering hiking, mountain biking, and zip-lining during the warmer months.
The nearby Catskill Forest Preserve further provides its visitors with miles of hiking trails, including the challenging Blackhead Range Trail, which offers some of the best views of the Catskills' many peaks. It is highly recommended you come here in the fall when New York's forests change colors in a magnificent fashion.
Windham’s charming downtown area should not be overlooked too, and within it you will find its selection of locally-owned shops, cafés, and art galleries, providing a more relaxing way for you to spend an afternoon while in town. The town of Windham also hosts some notable events throughout the year, including the Windham Mountain Fall Festival, a perfect addition to the amazing scenery the autumn months in the Catskills provide every year.
Skaneateles
Located on the shores of Skaneateles Lake, one of the lakes in the Finger Lakes region, this town is a perfect setting for anyone looking to spend a weekend by the water. Skaneateles is also known for its historic site from the state's earliest days, including 19th-century storefronts now housing locally owned shops, eateries, and other attractions that make it easy to spend multiple days here. The Skaneateles Historical Society Museum, for example, will give you a look into the town’s past and is housed in a former creamery on the lake.
At the heart of town, Clift Park provides lake access and views, and many visitors come here to launch their boat or take a guided lake cruise for a laid-back and scenic perspective of the area
Just outside of town, the wineries and distilleries along the Finger Lakes Wine Trail present you with a way to sample local vintages and spirits in this ideal growing region. Anyela's Vineyards is a highly recommended stop, known as much for its great wines as its spectacular views over Skaneateles Lake.
Annual events such as the Dickens Christmas Festival in December bring Victorian holiday charm to Skaneateles, drawing visitors during the winter months.
Cold Spring
A roughly 2-hour drive north of New York City, Cold Spring is a perfect escape from big city life for a weekend. Situated within the Hudson Valley, Cold Spring attracts visitors with its scenic beauty, both natural and man-made.
Main Street, the town's main thoroughfare, serves as the communities central hub. Lined with an assortment of antique stores, local eateries, and unique shops, a stroll along it is a great way to spend an afternoon. You can walk around the nearby West Point Foundry Preserve, a historic site that once played a vital role in New York's lucrative industrial base. It is now a place where many come to explore its trails, many of which contain interpretive signs that guide walkers through the industrial ruins.
For those interested in hiking longer distances, Cold Spring provides easy access to Hudson Highlands State Park, where destinations like Breakneck Ridge offer challenging trails with scenic views of the Hudson River and surrounding highlands.
Aurora
Perched along the eastern side of Cayuga Lake, another in the Finger Lakes chain, Aurora is a quiet village surrounded by nature. The town’s roots date back to incorporation in the 1830s, and many of its meticulously restored buildings are now home to inns, shops, and dining spots.
Looking for a spot to spend the night? The historic Aurora Inn, built in 1833, is a central draw, offering lakeside accommodations and a renowned restaurant serving up seasonal, locally sourced ingredients from this heavily agriculturally centered region of the state. Also, Aurora’s nearby wineries, part of the Cayuga Lake Wine Trail, allow visitors to sample wines in serene settings. Long Point Winery, located just south of town, is another winery in the area with excellent lakeside views.
Art lovers can explore the Wells College campus, which features the Long Library’s rotating art exhibitions and scenic lake views. The college also hosts a Peachtown Native American Festival annually, celebrating the cultural heritage of the region.
For outdoor relaxation, Cayuga Lake provides ample opportunities for boating, fishing, or simply relaxing along its lengthy shores.
Lake Placid
Famed for its Olympic history and eye-opening natural landscapes, Lake Placid is an ideal weekend retreat in the iconic Adirondack Mountains of upstate New York. Best known for hosting the Winter Olympics in 1932 and 1980, this resort town is home to the Olympic Center, a fascinating place where visitors can skate on the same rink used in the “Miracle on Ice” game or take guided tours to learn about the area’s sporting legacy.
Beyond its Olympic heritage, Lake Placid caters to outdoor enthusiasts year-round. Mirror Lake offers paddleboarding, kayaking, and fishing, while nearby trails provide access to High Falls Gorge, where a series of waterfalls and bridges allow for memorable nature walks.
For an unforgettable view, the Olympic Jumping Complex features a sky deck accessible by elevator, providing a unique vantage point over the town and mountains.
Ithaca
Ithaca is renowned for its nearby gorges, waterfalls, and vibrant food scene in town to top it off. Located at the southern tip of Cayuga Lake, the town is home to several stunning natural sites, including the 215-foot Taughannock Falls, which is taller than Niagara Falls! Be sure to also explore the Ithaca Falls and Cascadilla Gorge, both accessible via scenic walking trails within town limits.
The city’s culinary scene is another highlight, with the Ithaca Farmers Market offering a wide selection of local produce, goods, and prepared foods for sale. The town also boasts a range of restaurants showcasing dishes made with many of the same ingredients from the surrounding Finger Lakes region. As with many towns in this part of New York, several local wineries along the Cayuga Lake Wine Trail will provide you with tastings with more picturesque lake views. For something a little different, New York Cider Company is located just a short trip north of Ithaca and sources apples and other fruit from its surrounding orchards.
Saratoga Springs
A short trip north of Albany, Saratoga Springs combines historic charm with a vibrant entertainment downtown area. Known for its mineral springs and horse racing as well you are sure to have a weekend full of activity when you visit.
This town has attracted visitors for centuries who are drawn to its naturally carbonated mineral springs, which are believed to have healing properties. The Saratoga Spa State Park provides public access to some of these springs, along with beautiful walking trails, picnic areas, and the luxurious Roosevelt Baths & Spa for a higher-end mineral bath experience.
Known as the “Racing Capital of the World,” Saratoga Springs is also home to the Saratoga Race Course, where legions of equestrian fans and sports bettors alike can catch live thoroughbred racing each summer.
Downtown, Broadway, which cuts through the center of Saratoga Springs, is where historic hotels, including the stately Adelphi Hotel, and other amenities to serve you during your stay can be found. For some nighttime entertainment, the Saratoga Performing Arts Center hosts major concerts and ballet performances throughout the year.
Ticonderoga
Ticonderoga, located at the meeting point of Lake Champlain and the Lachute River, is a small town rich in history and surrounded by natural beauty. The town’s most prominent attraction is Fort Ticonderoga, a historically significant fort from the French and Indian War (broadly known as the Seven Years War), that is an exciting and educational destination to go to for reenactments, exhibits, and scenic views of the nearby Adirondack Mountains. Here, you can learn in detail about the fort’s other roles in the American Revolution and explore many of its restored structures.
For those interested in more outdoor-oriented activities during your weekend getaway, Ticonderoga is a community that is well-known for its ease of access to the Adirondack Mountains and the expansive Lake Champlain. The nearby Mount Defiance provides a chance for a shorter hike to a viewpoint overlooking the fort and densely forested are around it. Lake Champlain itself is a top-notch destination for boating, fishing, and scenic drives along its shore.
Ticonderoga is also on the edge of the scenic Crown Point State Historic Site, which has its own collection of hiking trails and historical markers to explore.
New Paltz
New Paltz rests at the foot of the Shawangunk Mountains and has gained a reputation as one of the best towns to spend a weekend at in the Empire State. Like many towns on this list, its beauty is notable and makes for a serene atmosphere; the opposite of what one might find in much larger cities.
The nearby Minnewaska State Park is the home of over 22,200 acres of hiking, biking, and horseback riding trails, as well as access to swimming and canoeing at the park's scenic lakes. To really get the adrenaline pumping, the Shawangunk Ridge is renowned for rock climbing and towering views over the area.
In addition to its natural beauty, New Paltz has a number of other kinds of draws. The town is also a center for arts and culture in upstate New York, with the Samuel Dorsky Museum of Art showcasing regional artists and SUNY New Paltz providing a space for various events throughout the year.
For history fans, the Huguenot Street Historic District will give you a glimpse into the town’s storied colonial past, with preserved stone houses dating back as far as the 1600s!
Northport
Situated along the North Shore of Long Island, Northport blends waterfront views, a small-town atmosphere, and easy access to New York City. An idyllic spot in New York for an oceanside escape, the town’s picturesque harbor is a great place to start your tour. Here you can enjoy boating, fishing, or stroll along the scenic waterfront park.
Moving on to Northport’s Main Street, you can explore several of this Long Island community's historic buildings and other local amenities, making it an ideal spot to explore on foot. Given its proximity to the Atlantic Ocean, make a point of grabbing a fresh seafood meal at some point. Skippers is a popular join right on the waterfront.
As far as other outdoor activities go, the nearby Sunken Meadow State Park is a place where walking and biking trails wind through the countryside, as well as a beach for swimming and picnicking.
The town’s strong community spirit is evident in its year-round events, including the Northport Arts Coalition's seasonal arts and crafts festivals. Northport also has a notable arts scene, with the John W. Engeman Theater offering Broadway-style productions and live performances throughout the year.
Experience the Best New York has to offer this Weekend
Do any of these 11 fantastic small towns in New York catch your eye? Escape the hustle and bustler of the city this weekend and explore these places to really get a sense of what else the Empire State has to offer, from idyllic vineyards to towering waterfalls, and lakeside picnics.
Make your next weekend escape a memorable one and see how many of these top-notch destinations you can fit into your itinerary!
