11 Top-Rated Small Towns In New York
You know it's time for a timeout when weekends blend into each other without easing your stress and city sights hone you down with reminders of chores. That's when you have to prescribe yourself some medicine, like disappearing into the colorful woods of the fall foliage or lying flat on your back under the summer skies, soaking up salty sea air. These towns, perfect for an anytime escape, have plentiful charming accommodations—waterfront and mountainside—have you skiing and holiday shopping this upcoming season and falling in love to return for another summer fling.
From a seaside affair in Greenport to the best of the Hamptons in Southampton, there's also racing Saranac Lake in the Adirondacks and Watking Glen with the Seneca Lake Wine Trail. Why complain over an impending work week when you can be having a blast at the Robibero Winery or Kettleborough Cider House with your honey on a couples retreat?
Callicoon
Even the name suggests a cozy cradle—that this town is in the foothills of the Catskill Mountains at the border with Pennsylvania. With eagles soaring overhead, this charming town is soaked in natural history, perfect for a daytrip or a whole weekend full of sightseeing opportunities along the Delaware River. With many water sports in the summer, you can spend a sunny afternoon kayaking or canoeing, rafting rapids, or floating belly-up in a tube. There is also great swimming and fishing with water access points from State Routes 52 and 17B, as well as five golf courses in the area. You can stroll to the scenic Stone Arch Bridge from 1880 and check out the Western Hotel from 1852 for a stay in Victorian architecture.
The Upper Delaware River Valley is great for self-guided hikes with picnic opportunities and wildlife around, while Delaware Youth Center has a summer program and rents space, perhaps for a private event over the weekend! The river and the mountains birth magnificent sunrises and sunsets, while those backroads are glorious on foot or behind the wheel during the fall, with nearby farmers markets for local wine, fresh cheeses, and produce. With regular music festivals and country festivals, there is also plenty for a rainy day, like museums, flea markets, antiques, art galleries, and unique shops. You can visit local artisans, pubs, and restaurants like Rafter's Tavern before a showing at the charming, full-screen, dolby digital surround-sound Callicoon Theater from 1948.
Cold Spring
This sweet village on the National Register of Historic Places, home to around 2,000 residents, sees flocks of tourists for its many well-preserved 19th-century buildings. The birthplace of General Gouverneur K. Warren, an important Union Army figure during the Civil War, Cold Spring, is steeped in history, but that is not all. Spoiled with nature, the Hudson Highlands are the deepest point of the Hudson River, just an hour away for the NYC locals via Metro-North Railroad to be enjoying breakfast here on an express getaway to unwind and recharge in a historic atmosphere with delicious places.
Big on beauty, the cute town with its candy-colored houses along the streets and waterfront makes a statement with the stark landmark of its iconic Bannerman Castle—a one-of-a-kind sight on this side of the "pond." You can start right along the waterfront, with pretty banks for strolls and easy-going recreation options like West Point Foundry Preserve. There's great kayaking along the Hudson River, as well as plentiful hiking trails around, most popular in the summertime, as well as prime rock scrambling, just one mile up Route 9D to the Breakneck Ridge! You can catch sight of the town's pretty strip under the dominating castle in the highlight of a sunset!
Greenport
This town, soaked through with sea and algae scents, sends off maritime vibes to all you seafaring fans and your little captains-to-be! There's nothing quite like Greenport, a sweet fishing village on Long Island's North Fork for top seafood eats, with friendly locals selling it fresh at markets and serving it up any style through charming restaurants. The sight of the serene waterfront with bobbing white sails is worth a thousand words to calm your soul on a morning stroll or under the highlight glow of a sunset. From the evoking town outwards, you will find farm stands along the highway through the countryside during a long and winding ride, so scenic in the fall!
Despite its in-your-face harborside beauty, Greenport stays humble against the neighboring hamlets, with a laid-back attitude welcoming families, workers, and students for a summertime along some of the cleanest sandy beaches, with incredible oysters and seafood ops right along the Peconic River. From a number of museums to wineries and breweries, there's something engaging with a pretty view for everyone in your gang! Just a quick train ride from Manhattan, you will feel at home in a heartbeat browsing eclectic galleries and vintage shops among the perfectly-lined lovely houses and places to mingle, like Little Creek Oyster Farm and Market.
High Falls
Although this town has all the essentials for a basic getaway, like antiques, unique shops, and great dining, High Falls has a certain personality that makes it unforgettable, with the natural spectacle in its name at the spectacular Rondout Creek. As a Hudson Valley hotpot brought to glory by its canal, you can learn more about its significance at the D&H Canal Museum in the heart of town by the canal's five locks. No impromptu escape is complete without unique sights and experiences like Woodstock Farm Sanctuary and the Wired Gallery.
There's great kayaking in the summer as well as the weekly Sunday flee market—what a wonderful idea to spend the morning of God's Day browsing for charms and local culture. Continue with the easy-going theme through little shops and art galleries along the D&H Canal Trail until it is time to dine at great restaurants, like Ollie's Pizza. The small upstate town has Hollywood ties to celebrities like Mandy Patinkin and Aidan Quinn as their hometown, as well as being the setting for the 1961 film Splendor in the Grass, with Natalie Wood and Warren Beatty's.
Kingston
Kingston is all prepped up on the west bank of the Hudson River, with strollable streets, historic landmarks, and the definitive architecture of this former first state's capital city! Just a small town, there is a neat configuration of the vibrant Uptown, the cultured Midtown, and the waterfront Downtown core, with historic buildings throughout. From funky shops in Uptown to museums and a trolley ride downtown, you can set off on a sightseeing boat cruise into the sunset. Return to the waterfront for its endless upscale restaurants and happening bars, or head back to midtown for a theater performance!
Naturally steeped in history, you will find beautiful architecture with a distinctive Victorian scene. From the Hudson River Maritime Museum's extensive exhibits to the cute Forsyth Nature Center, this family-friendly town delights with an intimate feel that calms away from the city. The Hudson River waterfront is unreplicable under the sun during the fresh spring and hot summers—the high season to visit Kingston. With live music, local events, and famous visitors, there's Kingston Point Park for a serene stroll and the Teddy Bear Picnic at the Den of Marbletown.
Mattituck
This little charmer between the Sound and Bay is for all you weekenders who love winning, dining, and boating with direct access to Long Island Sound via the Mattituck Inlet! With its idyllic waterfront views, Mattituck Inlet—a two-mile protected harbor leading to the sound—is home to some of the area’s finest and most distinctive homes. You can stroll the crooks and bends of the neighborhood streets, fitting the bay's shape, and around creeks that feed into Peconic Bay. Every season is rewarding, from the fall grape harvest to the summer's Strawberry Festival in June, over four lively days of local produce, amusements, and artisan booths!
Mattituck, where the North and South Forks of Long Island split, is made for a weekend affair with the sea. There is a slew of historic architecture, posh vineyards, and a vibrant downtown with its Love Lane thoroughfare aligned with locally owned restaurants, bakeries, and boutiques, perfect for a couple's escape! The nearby Harbes Family Farm has over 30 years of experience in its pocket of delighting families with pumpkins and cider doughnuts in the fall, a browsable market, a six-acre "barnyard adventure," mini tractors, and a hedge maze!
New Paltz
One of the Catskills' prettiest locales, the Shawangunk Mountains catch up with you wherever you are in this town. While there is no wrong place to stay in New Paltz, Mohonk Mountain House is a top-choice Smiley Family's resort from 1869. This Victorian castle of your dreams is right on the water, with kayaking from the door! Nearby, Historic Huguenot Street feels like a step back in time to "New Netherland, with preserved architecture from the 17th century!
The fall is the most stunning here, with perfect weather to connect with nature when the leaves are turning a million shades of red and orange. It is easy to find a perfect weekend stay with a bunch of options near adventures like biking, kayaking, and rock climbing hotspots in the Shawangunk Mountains. Main Course, or Lola’s Cafe, delights discerning foodies, while several bars keep you entertained late into the weekend night! From high tearooms to an afternoon spa trip, there's also Robibero Winery or Kettleborough Cider House for an intimate couples retreat!
Saranac Lake
This cozy town in the Adirondacks is a long-time favorite escape for a weekend in New York and the country in general. Full of small town charm, there's a lot of fresh air to get hyped up on, like the beach scene and live outdoor music shows in the summer. You can hit Mount Pisgah with skiing and tubing this winter and return in the summer with the kids to the 1.1-mile Moose Pond Trail, smooth enough for the little ones! The "cute cottage village" amid the Adirondacks refers to its architecture around the lake with towering mountain views, whether you're canoeing, kayaking, fishing, or prowling Main Street.
Here you will find local brands, boutique shops, and antique stores to stock up on memories and gifts, perfect during the enchanting winter season on an express holiday weekend spree. From skiing to snowshoeing trails and skating on the glazed-up surface, all flock to Saranac Lake for the town's fabulous Winter Carnival in February! Its one-of-a-kind ice palace, ice-skating races, fireworks, concerts, and tasty treats will be the highlight of your getaway, the season, and heck, set up the stakes for the rest of the year!
Southampton
Southampton, a seaport town in New York, boasts a scenic harbor on the south fork of Long Island. From the fringe of beautiful beaches with views of the city to bustling nightlife at its heart, there's no better destination that feels remote yet quick to get your hands on! Popular among daytrippers to enjoy an afternoon at the beach, Southampton is also the place to stay up with excitement late into the weekend night! If you don't have local friends in town, then Coopers Beach offers day passes for visitors.
You can spend a Sunday browsing through the quaint downtown area and its pristinely kept Main Street, with plentiful cafes and shops to get your mind off the impending workweek, or strengthen those muscles over some surfing and sailing in the summer. Popular year-round for the stunning views and selection of activities, Southampton, one of the largest hamlets in the Hamptons, is also the national center at the mouth of the Hudson River in the southeast corner of the state. Much more laidback than its neighbors, you will find easygoing spots like Sip 'n Soda, a classic '50s diner for the best ice cream with nostalgic vibes, and art at the Parrish Art Museum with local works.
Tarrytown
Tarrytown is a quintessential Westchester village on the east bank of the Hudson River, just 25 miles north of Manhattan, and a close neighbor to the even quieter Sleepy Hollow. You don't have to strain to hear the whispers along its historic streets, filled with treasures from the storied past. Tarrytown sports loud attire through every picture-perfect season, while the waterfront is its liveliest part. With local coffee shops and art galleries, the flower-adorned, cafe-filled main street offers a sense of unique culture, including the historic Tarrytown Music Hall for an evening performance.
The iconic writer Washington Irving's, a former resident, Sunnyside is an architectural masterpiece must-see, where you can decipher Tudor, Gothic, and Spanish highlights. The Tappan Zee Bridge, a New York State Landmark, is literally an unmissable three-mile, two-span bridge over to Rockland County with the best views across the Hudson River. Forget the nature trails, but visit the historic Lyndhurst Mansion, one of America's finest Gothic Revival mansions that will take a worthy chunk out of your day with a house tour, art, and rose gardens. Tarrytown House Estate hosts one of Hudson Valley's top restaurants, Goosefeather, under the James Beard-nominated Dale Talde's helm!
Watkins Glen
This village wedged into the huge Watkins Glen State Park is probably one of the most famous getaways in the Finger Lakes Region. The numbers of annual visitors don't lie, with the most popular season in the summertime, when the parks and greens weave all the way through town for you to enjoy a truly refreshing weekend escape no matter your pursuit. From its world-renowned car racing track to the remarkable cliffs and waterfalls a hop away, Watkins Glen is a truly one-stop shop for all.
Whether you're holding your breath over a Formula One Grand Prix race or breathing your lungs full of fresh scents on a hike along the surrounding trails, there are also vineyards and wineries all along the great Seneca Lake Wine Trail with deep flavors of diverse world-class wines! As one of New York's most picturesque towns, you will want to spend all your free time outdoors, which is easy here at the heart of the state park—choose your own adventure destination! From chasing all of the 19 waterfalls, the Gorge Trail along the Glen Creek is easy on feet and the eyes, while the colorful Seneca Harbor Park Pier beguiles for views at sunset!
It's time to get your act of weekend art together, relax, and really unwind away from the city that never quits or quiets down. It's pretty quiet where the North and South Forks of Long Island split in Mattituck between the Sound and Bay. With amazing restaurants, local shopping, and nature at your fingertips, you can de-stress without crowds in your favorite way!
From plentiful waterfronts and main street towns, these eleven will stretch your muscles, relax, and have you cool, calm, and collected to return a sharp-minded, better version of yourself! All exciting yet relaxing, and just a gas tank of gas away—just pick one from the list when you don't have time to spare or even plan.
