Small Towns In New York: Top 23 Most Unique Spots | Stanton House Inn
A picturesque town

Small Towns in New York: Top 23 Most Unique Spots

Hudson, a small town along the River

New York State is almost as big as all New England. So of course it hosts a trove of charming small towns. No matter which way you go:

  • The Hudson Valley

  • Long Island

  • Lake Erie

  • Or the Adirondack Mountains

You’ll find a patchwork of natural beauty, cultural attractions, and historic landmarks. Quaint villages and cozy hamlets offer a chance to reconnect with nature. These towns are the perfect retreat from city life. Each is a serene setting for relaxation or a playground for outdoorys types. Whether a quiet weekend away or a splash of adventure is in order, these small towns are a delightful escape from the City’s relentless pace.

Ready to explore the best small towns in New York State? Let’s get into it:

Quick hits

  • New York’s small towns are hubs for cultural, historical, and natural attractions. The Hudson Valley honors for its culinary scene and historic sites. Meanwhile, the Finger Lakes are famous for wine trails and scenic vistas.

  • Outdoor enthusiasts and arts lovers can find solace in the Adirondack and Catskill mountains. Coastal towns on Long Island boast beautiful beaches and a rich maritime history.

  • Venture beyond New York to the quaint towns of Connecticut, New Jersey, and the Berkshires in Massachusetts. These towns are rich in culture, history, and picturesque landscapes. Any is perfect for a day trip, or weekend getaway.

The Best Small towns in New York State

Aerial view of a small New York town alongside the Hudson River

Most equate New York State with the Big Apple. That said, it’s also sprinkled with enchanting small towns. These spots are havens for both locals and travelers. They offer that slower-paced, charming alternative to city life you’d expect. Trade:

  • The cacophony of city traffic for the serene rustle of leaves

  • Or the bright neon of Times Square for the gentle twinkle of fireflies on a summer night

Escape the concrete jungle for forests where trees are the only skyscrapers and Main Street parades are the only traffic jams. Whether you’re keen on:

  • Admiring fall foliage

  • Picking the freshest apples

  • Or exploring historic architecture

There’s a peaceful or adventurous retreat for every taste. These small towns serve up a slice of upstate New York heaven just for you.

Picturesque Hudson Valley Towns

Historic main street of a quaint town

Head north from the City and into the Hudson Valley. The scenery here is a feast for the eyes:

  • Rolling hills

  • Meandering rivers

  • And an enchanting blend of rural and suburban landscapes

The region’s commitment to gourmandizing shines in its vineyards and the Culinary Institute of America. Farm-to-table dining is a way of life here, and it garners applause from foodies and critics alike.

Cultural activities flourish in the Hudson Valley, and historic preservation is a point of pride. Take the town of Hudson, for example. Its well-preserved historic buildings are the canvas for a vibrant arts scene that pulses with creativity.

Tarrytown

The first town on our list, Tarrytown, NY, invites you to enjoy its outdoor activities. Walk or bike the trails at Tarrytown Lakes Park, or take part in waterfront activities at Pierson Park. The cultural scene thrives here with venues like:

  • The Irvington Town Hall Theater

  • And the historic Tarrytown Music Hall

Be sure to visit the Lyndhurst Mansion to admire its Gothic Revival architecture. Another historic site is Patriots Park. The Captors’ Monument here commemorates the capture of a spy during the Revolutionary War.

Sleepy Hollow, New York

Oceanus Fountain, the entrance to Kykuit: the Rockefeller Estate, in Sleepy Hollow, NY

Sleepy Hollow, New York, our next stop, relishes the fame that the lore of Washington Irving’s:

“The Legend of Sleepy Hollow”

And its infamous Headless Horseman

Brought to it. So much so, that they changed the town name to match it. Far from being a local haunted legend, this small town draws thousands of tourists each year. That goes doubly so for its Halloween festival. But be sure to explore its historic sites while you’re here. They’ve inspired many film and television adaptations.

Outdoor activities here include:

  • fishing

  • kayaking

  • hiking

  • biking

  • horseback riding around the Rockefeller State Park Preserve, located near the Delaware River

The Sleepy Hollow Cemetery is a top attraction, both for fans of the macabre and history.

Croton-on-Hudson

Croton-on-Hudson invites a hike or bike ride on and above Croton Gorge Park. Don’t miss the Great Jack O’Lantern Blaze. Over 7,000 hand-carved jack-o’-lanterns illuminate the night each October.

Check out hip eateries like Croton Tapsmith and Ocean House Oyster Bar & Grill while you explore town.

Pleasantville

Pleasantville is another delightful (and easy) escape from city life. Here are some highlights of what you can enjoy in this charming town:

  • A pristine downtown with a picturesque gazebo

  • World-renowned filmmakers’ works at the Jacob Burns Film Center

  • Culinary journey at the Blue Hill Stone Barns, only a short drive away

Cold Spring

Hudson River view near Cold Spring, NY

Long before Don McLean wrote “American Pie” here, Cold Spring, NY, was a slice of Americana. Meticulously preserved 19th-century buildings line its main street down to the Hudson River. The town offers a variety of outdoor activities such as fishing, swimming, and kayaking along the Hudson River. Some of the best hikes in the Hudson Valley are near here, including the Breakneck Ridge hike. Make sure to explore the town’s quaint center, where cozy cafes, unique boutiques, antique shops, and restaurants await.

Beacon

On the other side of the Hudson Highlands is Beacon, New York, a town that has:

  • Preserved Victorian homes

  • New farm-to-table restaurants

  • Art galleries

  • Museums

  • Dia:Beacon, a hip museum of contemporary and modern art

Ex-pat New Yorkers and Brooklynites adore Beacon. As does this innkeeper.

Whether it’s walking nature trails, admiring hillside views, or exploring Dia:Beacon, visting Beacon is always a good idea.

Rhinebeck

Rhinebeck is that quaint little town where time seems to pause, nodding to the specialty shops and historic estates. Here, the restaurant scene buzzes, and the antique shops and home décor stores are scattered treasures. For a touch of adventure, the Old Rhinebeck Aerodrome invites you to soar in a vintage 1929 New Standard D-25. On the ground, Ferncliff Forest beckons for climbing, mountain biking, and camping.

Kingston

Deer walking through snow in Kingston

Kingston, New York, is a cultural and historical hub. It’s home to the historic Stockade District and the Senate House State Historic Site. The Rondout District, along with the Trolley Museum, is a charmed glimpse into the state’s transportation history. Art and culture thrive here, complemented by a diverse culinary scene that ranges from cozy cafes to upscale dining. The district’s stone buildings house charming shops, antique stores, galleries, and boutiques. Spring and summer weekend getaways in Kingston are perfect for:

  • Outdoor concerts

  • And scenic boat cruises

Explore the exhibits at the Hudson River Maritime Museum and Kingston Point Park.

Hudson

Hudson, known affectionately as “The Friendly City,” may be small with its 7,000 residents, but it’s big on charm.

  • Orchards

  • Galleries

  • Breweries

Provide a sensory smorgasbord among the many things to do in Hudson, NY. It’s a favored retreat from Manhattan. This is a must-visit if you have a penchant for mid-century antiques and contemporary art. Dining options range from the nostalgic Grazin’ diner to the chic Swoon Kitchenbar. For antique lovers and collectors, the town is a goldmine. And Warren Street boasts well-preserved historic buildings like the Hudson Opera House. The Olana State Historic Site, once home to artist Frederic Edwin Church, is a monument to the town’s rich artistic heritage.

Catskills Hideaways

Idyllic rural landscape of the Catskills region

Head into the Catskill Mountains to uncover a trove of artsy hideouts and antique-laden nooks. It’s like stepping into a Norman Rockwell painting, but with Wi-Fi!

Sometimes.

These hideaways are a delightful mash-up of yesteryear charm and today’s comforts. They’re the perfect backdrop for a digital detox—should you choose to resist the siren call of your smartphone, that is.

New Paltz

New Paltz is a vibrant, youthful college town with a history dating back to 1678. Known for its:

  • Picturesque historic buildings

  • Lively bars

  • And unique boutiques

The town is also home to the Victorian-era Mohonk Mountain House resort. It’s both a hotel and a National Historic Landmark. Its own private preserve, the Mohonk Preserve, surrounds it. Outdoor enthusiasts will love hiking some of the best hiking trails in upstate NY and biking around the Wallkill Valley and Shawangunk Range. The Wallkill Valley Rail Trail offers over 21 miles of scenic caves and woodlands to explore. Cultural attractions include the Samuel Dorsky Museum of Art, and the historic Huguenot Street. Main Street and Water Street Market provide even more spots to explore, including one of the best antique shops in upstate NY.

Woodstock

Woodstock, founded in 1787, is most famous for something that happened about two centuries later.

And, fun fact, didn’t even happen here.

That said, it continues to thrive as an arts and crafts colony and draws artists, musicians, and theater enthusiasts. It occupies a picturesque setting of mountains, forests, and Upstate New York lakes. While you’re here, be sure to:

  • Browse Tinker Street’s shops

  • Savor local cuisine with vegan options

  • And find tranquility at the Karma Triyana Dharmachakra Tibetan Buddhist Monastery

A two-hour drive from Manhattan brings you to Woodstock, where Hudson Valley hiking trails like those at Kaaterskill Falls await. The town also hosts the Woodstock Byrdcliff Guild and Tinker Street Cinema. Cultural highlights include the Woodstock Playhouse and the Woodstock Film Festival.

Saugerties

Saugerties Lighthouse

Saugerties, NY, boasts eclectic antique stores and vintage shops, complemented by quality restaurants. Among them, The Red Onion stands out with a vegetarian-friendly menu and a Wine Spectator Award. Explore Cantine Dam Falls or marvel at Opus 40, a large environmental sculpture. The Saugerties Lighthouse is a must-visit, too.

Phoenicia

This hamlet in Ulster County, is celebrated for its arts and antiques. Charming downtown Phoenicia plays host to an array of shops, restaurants, and places to stay. The area is a hub for outdoor enthusiasts, with hiking trails and skiing in the winter months. Notable dining establishments include the Phoenicia Diner and Woodstock Brewing. Art lovers can enjoy the Brunel Sculpture Garden. Phoenicia also plays host to significant cultural events such as:

  • The International Festival of the Voice

  • And the Shandaken Artist Studio Tour

Narrowsburg, NY

This is another tiny town in a prime spot in the Catskills mountains along the scenic Delaware River. Narrowsburg, NY, is a hub of creativity, with pop-up shops and art studios. Discover the Fort Delaware Museum, enjoy a stroll on Main Street, and take in the beauty of the Upper Delaware River. Popular outdoor activities here include canoeing, kayaking, or floating down Skinner’s Falls. Sample the local cuisine with takeout from The Heron for lunch and a meal at The Laundrette for dinner. Stop by Tusten Cup and 2 Queens Coffee for your coffee fix and head to Lander’s River Trips for rental equipment.

Adirondack Mountain Retreats

Sunset over the Adirondack Mountains in upstate New York

Venture north to the Adirondack Mountains, where the air is crisp. This region is a unique blend of rustic luxury and wilderness. Ski down slopes that glisten like diamonds or inhale air so pure it feels like a city detox. These mountain towns provide a fusion of rustic elegance with exhilarating outdoor adventures.

Lake Placid

A placed that the 1932 and 1980 Winter Olympic games would of course offer a variety of outdoor activities for all seasons. At the Olympic Sports Center, visitors can experience the thrill of:

  • The Speed Skating Oval

  • Whiteface Mountain

  • Cliffside Coaster

  • And the ski jumping complex

The town itself is also a hub for shopping, dining, breweries, and wine tasting rooms. The encircling Adirondack Mountains invites you to hike, mountain bike, swim, kayak, ice-skate, or toboggan. Or a mix of them all, just not at the same time.

Lake George

Canoes on a dock on Lake George

New York City is a popular summer resort town, famed for lakeside cabins and resorts. It offers historic steamboat cruises, a unique way to chase fall foliage. The town is home to two public forts, Fort William Henry and Fort Ticonderoga. It also boasts Splashwater Kingdom, New York’s largest amusement park. Visitors can enjoy a panoramic view from Prospect Mountain and water sports like:

  • Boating

  • Swimming

  • Whitewater rafting

  • And stand-up paddleboarding

Saranac Lake

Saranac Lake, a historic village boasts cure cottage architecture and the Moose Pond Trail. Founded in 1819, it is renowned for its clear mountain air and outdoor activities, including a festive Winter Carnival. While you’re here, engage in watersports, visit art galleries, and explore historic sites. The town gained fame for its role in treating Tuberculosis patients with its rejuvenating mountain air. A feature it still offers to this day. It also offers a picturesque lake and an array of shops, restaurants, hotels, and stunning architecture.

Finger Lakes Region Gems

Scenic view of a charming town by the Finger Lakes

Heading westward, and set your sights on the Finger Lakes region. These storybook towns boast a history as full-bodied as their world-class wines. Sip a crisp Riesling with a breathtaking view, or meander through historic landmarks. These towns, much like a fine vintage, improve with each passing moment. It’s a slice of lakeside serenity and a taste of the good life.

Aurora

The charming little town of Aurora, NY, boasts:

  • The liberal arts institution Wells College

  • And the Victorian Tudor-Revival style Morgan Opera House

Wells College is the alma mater of Pleasant Rowland, creator of the American Girl Doll Company. And she has restored many old homes and businesses in the area.

The town’s lakeside setting is complemented by its wineries and breweries. Indulge in biking along the Cayuga Lake Wine Trail or exploring Long Point State Park. With its well-preserved historic homes and college buildings, Aurora is as an idyllic retreat.

Seneca Lake

Bridges and icicles at Watkins Glen State Park.

Seneca Lake is a must-visit. To be frank, it’s hard to pass-by:

  • The Seneca Lake Wine Trail

  • And the awe-inspiring Watkins Glen State Park, home to 19 cascading waterfalls

The 1.5-mile Gorge Trail provides breathtaking views of the lake, while Franklin Street is the go-to for dining and boating. Nearby, the village of Montour Falls showcases the stunning She-Qua-Ga Falls, recognized in the Louvre. And the close-by Havana Glen Park offers hiking trails amid the beauty of even more Finger Lakes waterfalls.

Ithaca

Ithaca is the quintessential college town of New York State, home to both:

  • Cornell University

  • And Ithaca College

Both of which infuse the town with a youthful atmosphere. The area thrives with arts, culture, and nightlife. Bookshops, restaurants, theaters, and a variety of dining options fill the downtown area. And all in a picturesque location at the southern tip of Cayuga Lake. There are also over 150 waterfalls within nearby gorges, forests, and state parks surrounding the town. Take pleasure in hikes through magnificent gorges, including the town’s renowned Ithaca Falls. And the Finger Lakes region boasts extra natural attractions such as Fall Creek, Cascadilla Gorge, and Six Mile Creek. Enjoy local wineries, breweries, and scenic New York state parks, including

  • Robert H. Treman State Park

  • Buttermilk Falls State Park

  • Taughannock Falls State Park

Long Island’s Coastal Escapes

Dock in Greenport

We now pivot to the coastal sanctuaries of Long Island. Here, the salty sea air and whispering waves set the stage for both relaxation and adventure. These towns are not just about sandy leisure; they’re treasure troves of culture and history. So, swap your city shoes for barefoot strolls as we explore the unique charm these shores have to offer.

Greenport

Founded in 1682, Greenport exudes charm with:

  • Relaxed atmosphere

  • Pristine beaches

  • Eclectic galleries

  • And quaint shops

This country town is famous for Lavender by the Bay, a fragrant lavender field, and a rich selection of wineries. Other fun things to do in Greenport, NY, include:

  • Embarking on vineyard tours

  • Savoring fresh local cuisine

  • Sailing

  • And exploring the Oysterponds Historical Society

Greenport is as an idyllic wine country retreat on Long Island’s North Fork.

Montauk

Dog in a shop in Montauk

The easternmost point of Long Island, Montauk beckons visitors with its array of attractions. Explore the iconic East Coast lighthouse, relax on the beaches, and enjoy local dining and entertainment options. Surfers flock to Ditch Plains Beach, while Camp Hero State Park offers breathtaking views of the ocean and the lighthouse. Seafood lovers are in for a treat at Clam Bar, Lobster Roll, and Harvest on Ford Pond, as well as Duryea’s Lobster Deck.

Sag Harbor

Nestled in the Hamptons, Sag Harbor is celebrated for its historic homes and Main Street. It provides a refreshing escape from both New York and Boston. And while you’re here, be sure to:

  • Explore the Sag Harbor Whaling & Historical Museum

  • Browse the unique offerings at Jayson Home

  • Unwind at the waterfront marinas

The town’s rich history as a significant whaling port during the 18th and 19th centuries is evident in its cultural landmarks. The village boasts spots like the Dockside Bar & Grill and a cinema featuring the classic Sag Harbor facade.

Freebie: Cooperstown

This small town is a haven for writers and artists that offers tranquil lake views and a picturesque countryside. And yes, the National Baseball Hall of Fame. Established in 1786, Cooperstown is proud of its historic district. Visitors flock to Cooperstown for:

  • The Farmers’ Museum

  • Diverse art galleries

  • And the summer allure of the Glimmerglass Opera Festival

The town’s cultural life is enriched with offerings of art, music, and antiques; alongside activities like golf and horseback riding.

More cute towns to explore nearby

Sunset over a harbor in an adorable small town in Connecticut

Wave goodbye to New York’s hidden gems, be sure to broaden your horizons. A quick jaunt away lie the charming small towns of Connecticut, New Jersey, and the Berkshires in Massachusetts. Each one is a unique destination with its own allure. And there are even more charming New England towns to explore, further north and east of here.

Connecticut’s Cozy Corners

Connecticut may be compact, but it’s brimming with charm. Picture a storybook setting where every cute Connecticut town tells a tale. The Connecticut Antiques Trail is a treasure hunter’s dream. And Connecticut fall foliage competes with the finest art in its vibrant display.

New Jersey’s Hidden Gems

Cross into New Jersey to uncover a mosaic of small town, each with its own slice of Americana. Far from the busy highways, these day trips in New Jersey offer:

  • Serene beaches

  • Lush gardens

  • And a sense of community as comforting as a home-cooked meal

The Berkshires’ Artistic Retreat

The Berkshires of Massachusetts are a sanctuary for the arts. Here, creativity flows as freely as the rolling hills, and the historic stages whisper with echoes of the past. The quaint towns nestled in these hills offer a peaceful retreat, inviting you to unwind and recharge. A few to explore include:

Tl;dr

Our journey has taken us through a narrative rich with enchanting small towns in New York and its neighbors. They stand as serene alternatives to the relentless pace of city life. When the urban grind becomes too much, remember that these tranquil havens are just a short trip away, ready to welcome you into their quiet embrace.

Frequently Asked Questions

What is the best small town in New York?

The best small towns in New York include Chittenango, Westfield, Canandaigua, East Aurora, Goshen, Sag Harbor, City Island, Alexandria Bay, Ithaca, Lake Placid, Aurora, Cooperstown, Beacon, Greenport, Saratoga Springs, and Albany. Each town has its own unique charm and attractions.

Is there rural areas in New York?

Yes, there are rural areas in New York, with about 21.5% of the state’s population living in rural counties. These areas vary from the Adirondacks to the rolling hills of Wyoming County.

How many small towns are in New York?

There are 933 small towns in New York, according to the 2020 United States population census.

What are some of the activities one can do in these small towns?

You can explore local history and culture, enjoy outdoor activities like hiking and boating, visit art galleries, and savor local cuisine in these small towns. There are plenty of options to choose from and something for everyone to enjoy.

Can I visit these towns as a day trip from New York City?

Yes, you can visit these towns as day trips from New York City since they are within a few hours’ drive. Enjoy your getaway!

 

Leave a Reply

Your email address will not be published. Required fields are marked *