11 Prettiest Towns in Upstate New York
New York is full of pretty towns, very different from the NYC scene in the best way. Escape New York City and enjoy the easy access or remoteness of some towns to feel the farthest from the daily stressors amid the enchanting nature. The rural, bucolic sights of the Adirondacks and Catskills will keep you outside all day with breathtaking adventures that won't let you stop exploring. Visit a town in the pretty Hudson Valley, just north of the boroughs and beneath Albany, with easy access by train, bus, or car from the Big Apple.
Enjoy a day trip or a weekend escape from New York City to surround yourself in the beauty of the Catskill Mountains, just west of the Valley, across the river. Visit the Queen of Lakes in Lake George, or perhaps Ithaca, the famous college town full of bright minds, to dispel all "farmers and hillbillies" rumors about the Upstate. The lovely and friendly residents enjoying the sunshine and pretty sights are not in the poorer region either. Sightsee the stunning architecture, waterfronts, and priceless countryside of fertile farms and rich wine trails.
Bethel
Bethel, a pretty-faced town some 70 miles southwest of the town of Woodstock, welcomes music fans and their friends. Home to Yasgur's farm and the host for the real, famous Woodstock Music Festival, find the town molded by the unforgettable 1969 festival for a dive into the counterculture of the era. Explore the festival grounds and learn about the history and what happened here at the Bethel Woods Center for the Arts, the "pasture" for 500,000 fans that year in mid-August.
Tour the Museum at Bethel Woods for deep insights into the 1960s cultural and social changes leading up to the historic music festival. The touristy town meets and greets tourists like a pro, boasting a wide array of attractions for all. Come at the end of May for the nowadays renowned Mountain Jam, the largest, longest-running rock-n-roll music and camping festival in the Northeast, a multiday, multistage event at the original Woodstock festival site.
Canandaigua
Canandaigua Lake, the childhood summer roaming grounds for Humphrey Bogart, the American star from Casablanca, is not just any cottage resort town. As pretty as it gets, just an hour south of Rochester, enjoy easy access from NYC to find its prettily perched scenery along the northern tip of the namesake fingerlike lake to enjoy your own best summerscape. Connect with the abounding nature in your favorite laidback or active style, whether through water sports, scenic walks, or relaxation at the views of the tranquilly sparkling surface. Slice it with a canoe or kayak and take a spectacular sunset boat ride or a cruise into the horizon, looking back at the pretty little town behind.
The Canandaigua Lady, a charming old-style double-decker paddle wheeler, the primary mode of transportation here in the 19th century, is a pretty cool way to enjoy the scenery over a relaxing paddle for a cherishable memory with a loved one. Travel back to the Victorian Era along the downtown's architectural galore and through the stunning Sonnenberg Gardens and Mansion State Historic Park, with its 40-room Queen Anne mansion on a "sunny hill" and acres of blooming gardens from April through October. The renowned Canandaigua City Pier offers a perfect place for selfies and lingering for the water views, spreading hundreds of miles of scenic tranquility in front of you.
Cold Spring
Boasting a National Register of Historic Places spot, this pretty Putnam County town, just a hop from NYC, is a top choice among city dwellers to escape for a memorable weekend. With so much to see and do in the lively atmosphere, you can enjoy something different each time in between your old favorite local spots to relax and stay active. Sightsee the quaint, restored 19th-century architecture on a downtown stroll through the galore of independent shops for the most unique finds to capture with your camera and bring a gift home for a friend. Take an epic free art stroll through a private collection of post-war and contemporary Italian art at the town's old computer factory turned Magazzino Italian Art gallery.
Complete with a beach and everything you need for a sunny day picnic, pack your gang, a take-out, or a to-go lunch from the Cold Spring General Store for a party, a quiet gathering, or a romantic escape by the waters. The nearby Hudson Highlands, with views of the Hudson River and the countryside, offer hikes like summiting Bull Hill or Breakneck Ridge. Get in touch with nature at your fingertips on a bike ride, a boat trip, or via kayak, a stone's throw away from the best shopping, dining places, and charming bed and breakfasts for after-outdoors fun, food, and rest.
Ellicottville
Skiing in New York? This small town in the west of the state has stunning slopes! Ellicottville, in an underappreciated region of New York, astounds with the number of year-round adventures at your fingertips. Visit for the winter wonderland at Holiday Valley Resort and HoliMont Ski Club, or on a great summertime escape without crowds for the best perusal around the downtown's cozy shops in a close group. Enjoy complete oneness with nature on a springtime or fall foliage hike with numerous picnic areas in Ellicottville Village Park.
Aside from the two ski slopes and ample trails for hiking and mountain biking, die-hard anglers also find some of North America's best waters here, teeming with fish in surrounding Cattaraugus County. Find golf and an aerial adventure park at Holiday Valley Resort, and look no further than a stroll from your hotel or rental for evening fun, from local boutiques to impressive restaurants and a great bar scene. Once you're all played out, head to Spaghetti & Meatballs at Dina’s, sink your teeth into a 24-ounce Ribeye at West Rose, or try the famously Loaded Brewer Tots at Ellicottville Brewing Co. over a frothy drink.
Ithaca
Ithaca, the famous college town, is incredibly beautiful in the Finger Lakes region. It is a real dream come true small-town escape for historians and wet-pursuit fans with water access for hundreds of miles, as well as those seeking to relieve the youth without the studying part. Find plentiful charming shops, cafes, and bookstores offering students a place to hang out post-class while you relax, dine, and browse for unique gifts. With its own airport, you can enjoy easy access from any part of the state, as well as Amtrak trains from NYC, in lieu of driving from the nearest city, Albany, which is at least three hours away. Take a shoreline stroll along Cayuga Lake, a favorite place to study and blissfully serene throughout the summer without student crowds.
The stunning natural beauty here offers an outlet to work off those sore muscles after bending over the books in the fresh air and astounds the every-day tourists from the doorstep like spectacular fall foliage on an early morning serene stroll. Join the locals in chasing some of New York's finest waterfalls, like the two impressive cascades of Ithaca Falls' 45-meter plunge into Cayuga Lake right at the heart of the city. Seek out the tallest cascade in the Finger Lakes area, Buttermilk Falls, among many others, while hiking around the landscape, rimming gorges, and enjoying some rock climbing. The thriving local culture is a scene of its own, with a galore of unique restaurants for all tastes, as well as galleries and live music events.
Lake George
Presenting: the birthplace of the American vacation, with just over 1,000 residents. Upstate New York's shining gem in the Adirondacks is a no-joke, generations-proven destination for the best summers. Escape with your favorite gang to see what it is all about here at the southern tip of the breathtaking, 32-mile-long "Queen of American Lakes." From swimming, boating, and fishing to sightseeing through uncrowded shoulder seasons, Lake George's quaint downtown architecture will steal the last of your breath away.
Find several scenic drives on a rainy day, like the Prospect Mountain Veterans Memorial Highway, for the phenomenal Adirondacks, and bundle up in the cold-weather months at a cottage with views in between skiing, snowmobiling, and ice fishing. Continue further to discover more natural wonders around Lake Luzerne, or travel 30 minutes to Saratoga Springs to experience both towns. The 6 million acres of the nearby Adirondack Park will keep you coming back for more of its three times as much expense for sights and pursuits as Yellowstone National Park.
Lily Dale
Lily Dale is a tiny and incredibly pretty town that is fun to discover in Upstate New York, just under 15 scenic miles from Lake Erie's shores. Take a stroll through the compact yet attractive downtown area, and you will start to notice a unique culture of Spiritualists. Earning Lily Dale the title of New York’s Seance Capital, the hamlet of barely 300 year-round souls sees thousands of new curious faces and returning visitors for its one-of-a-kind scene.
While most seek to delve into the paranormal, which somehow feels more attainable here, the New Age attractions are exciting for every taste. Learn about the history behind this pioneer movement at the Lily Dale Museum inside a former school, and stroll a few blocks over to the Lily Dale Assembly for regular events and activities. Mingle with plain mortals and skilled mediums at Lucy’s Coffee Shop, right in the town's heart, where all the mystic vibes collide and seem to be more potent.
Rhinebeck
Rhinebeck is a really cool town that many come to visit for the indie-shopping scene, like Montgomery Row's whole block of quaint shops. As the cultural mecca of the region, there is a concentrated amount of pretty sights with picture-perfect views every way and a lively atmosphere around each corner as you browse through some highlights. Visit the family-beloved Land of Oz Toys, Hummingbird Jewelers for one-of-a-kind charms, or Periwinkles for local artisanal works. Stop by Krause’s Chocolates for a treat before more card-swiping businesses at Paper Trail and Olivia! Gourmet Olive Oils for gifts, or drop by Clear Yoga or Breathe Studio: Barre & Pilates.
Come to the renowned annual agricultural fair, the Dutchess County Fair, for more culture, crafts, and fresh food, with Catskills views right from the town. Just two hours north of New York City, the Dutchess County town on the east side of the Hudson River in the Hudson Valley offers nature with open views to roam for miles along several hiking and biking trails and a range of restaurants to recharge after. Feel yourself rejuvenated after all the farm-to-table dinners, sprint shopping sprees, and dancing to live music. Watch a movie or a theater performance and grab a treat from Samuel’s Sweet Shop, owned by Paul Rudd, for some culture and balance. After a brunch at The Corner by Hotel Tivoli, visit the Beekman Arms, the oldest operating inn in the US, or perhaps hike to an observation tower in the 200-acre Ferncliff Forest.
Saugerties
The pretty town with a name that just rolls off your tongue in a honey-scented breath is an unmissable destination in New York. Visit to make memories over feel-good pursuits for the entire family, a group of friends, or couples on escape. Sightsee the iconic Opus 40 for a must-take selfie with this "Stonehenge of North America," inspired by the architecture of the Aztecs and Mayans, stark against the surrounding greenery. Take a stroll around this abandoned quarry and linger in the fresh air over a picnic at the side of the impressive stone artwork by artist Harvey Fite on a sunny day.
Just a quick hop from Woodstock and only 60 miles southwest of Albany, Saugerties is home to the Woodstock Museum, about the famous music festival that shook this part of the state in 1969. Immerse yourself in its local, epicurean-like lifestyle on the west bank of the Hudson River for days wasted amid lush shores over strolls, picnics, and summertime water pursuits. Take a stroll to the Saugerties Lighthouse, beckoning a photoshoot with its red-brick facade nearly two centuries old and lonely profile at the end of a narrow peninsula into the Hudson River. For a unique insight, take a Sunday guided tour or even fill the role of a lighthouse keeper when you stay a night at one of the two bedrooms on the second floor with the best views.
Skaneateles
This gem of the Finger Lakes region is a destination that seeps romance from every pore. From its namesake, a cottage-bounded blue lake, to the rich lushness of the surrounding wine country, Skaneateles cannot be a prettier town for sightseers. Just 30 minutes west of Syracuse, the town transcends the city in many ways, like the pastoral European postcard sights of fuzzy grazing lambs and the fragrant bushes at the Lockwood Lavender Farm. Find plentiful charming inns and B&Bs to stay longer in this natural wonderland, and try all the unique restaurants throughout the historic downtown district.
Enjoy market strolls amid the bounty of fresh produce thanks to the fertile grounds of the Lakes Region, and find lavender along the northern tip of Skaneateles Lake for real inspiration for your French countryside picnic. Escape with your girls or your lover for vineyard strolls and bankside picnics, with an evening spent wine tasting local creations. The cold-weather grapes in their perfect environment here produce wines throughout Eastern Europe, while the Last Shot Distillery is a perfect stop after a day hike along the renowned Charlie Major Nature Trail to unwind with your favorite people.
Watkins Glen
Perhaps the most famous town Upstate, Watkins Glen is a naturalist's gateway to the renowned Watkins Glen State Park, with a bucolic feel to enjoy active pursuits and relaxation as you like. Find the town at the pretty crossroads between Seneca Lake and the Chemung River, with regular summertime festivals along the banks and a rich auto racing history throughout the 20th century. Visit Watkins Glen in time for one of the lively events that bring cross-country fans, and stay for the vibrant season of hiking and fishing, where you can spend a whole vacation on a budget while camping at the park.
Enjoy its truly magical nature from the doorstep with forested trails that inspire you to go on a lucky charm hunt and find a real pot of gold in rainbow-reflecting waterfalls, creekside picnics, and serene fishing for rainbow trout. Used to handling the fleets of tourists with quality products and impeccable services, the sweet town has got you covered with provisions and amenities after summertime ventures and foliage hikes. The Seneca Lake Wine Trail will delight all connoisseurs with fruity cabernets and bold pinot gris from its 30 wineries around the lake. Nothing tastes better after a hike than a sweet iced wine on a hot summer's evening!
These pretty towns are like sugar-coated delights in pretty wrappers with gooey centers to uncover in the Upstate. Sights abound here at each step, and discoveries topple one on top of the next, a hand's reach from natural adventures.
Enjoy the rich wine-producing trails through the area, lavender fields for French-inspired picnics and pictures, and plentiful waterfalls to chase in this part of the state. Visit a beach town in the summer with waterfront attractions or hit up a mountain gem for a hot day hike through the refreshing nature.
