The 9 Friendliest Little Towns In Upstate New York
Upstate New York's friendliest small towns know how to make you feel like you have been part of the community for years. Annual festivals and hometown events pull in visitors from across New York, Pennsylvania, Vermont, Massachusetts, and even the rest of the US. The rush of tourists turns quiet streets into full-on celebrations, and that is the point; everyone's invited to the party. Towns like Lake George, Margaretville, Lake Placid, and Corning fill weekends with massive balloon festivals, athletic competitions, Oktoberfests, and incredible winter carnivals that make even the coldest days incredibly warm and welcoming.
Lake Placid
Lake Placid is undoubtedly a hub for winter sports. It hosted the Winter Olympics twice, after all. Naturally, the town welcomes skiers, boarders, and the like to nearby Whiteface Mountain every season. Seasonal events, such as the Holiday Village Stroll in December, coincide with Lake Placid's most popular time for visitors. But the upstate New York destination isn't just about wintertime activities. When fall rolls in, the Flaming Leaves Festival turns the Olympic Jumping Complex into a huge community hangout, with food trucks, live music, vendors, and families packed along the jump tower railings watching ski jumpers launch like it is the most normal thing in the world.
During July's annual IRONMAN weekend, athletes from all over the world come to Lake Placid to compete. Then there is the Lake Placid Film Festival, which has a similar international draw, though this time the town invites a decidedly more artsy crowd. Whatever the season, Lake Placid has something to welcome everyone.
Woodstock
With its ties to the famous 1969 music festival of the same name (even though the event took place in nearby Bethel), it is no wonder that Woodstock is a major destination in upstate New York. Music and history lovers are welcomed with open arms, but it's not just them. Woodstock is decidedly artsy and spiritual, which makes it a gathering place. This is particularly true in October when the Woodstock Film Festival takes over town. The screenings aren't just about movies, as the whole town becomes a party, with businesses along Mill Hill Road and Tinker Street benefiting from the sometimes A-list celebrity guests.
Autumn is one of the best times to visit Woodstock. The changing leaves around Catskill Park and the nearby Catskill Mountains bring in a host of visitors. Many want to appreciate the seasonal shift by hiking the Overlook Mountain Trail. Another reason people love to visit Woodstock is the Karma Triyana Dharmachakra, a Tibetan Buddhist monastery located less than 10 minutes away from downtown. This remarkable place welcomes guests to see, pray, and learn about its history.
Lake George
The village of Lake George sits at the southern end of the namesake lake, right where the Adirondacks start rising. September brings the Adirondack Balloon Festival, a tradition since 1972, and easily one of the most welcoming weekends in the region. Families, longtime locals, and first-timers crowd the launch fields as massive balloons lift into the air. While it is just outside of town, the event makes Lake George a home base for the festivities due to its proximity.
In October, Lake George Oktoberfest turns Canada Street into a three-day block party with polka bands, stein-hoisting contests, and carnival rides. Winter doesn't quieten anything down when it comes to friendly and welcoming events. This includes the Lake George Winter Carnival, which fills four back-to-back weekends with cook-offs, races, and lakefront events that make the coldest part of the year one of the most fun.
Margaretville
Along the East Branch of the Delaware River in the western Catskills is the town of Margaretville. Without a doubt, the annual Cauliflower Festival at Village Park is one of the biggest draws. The September event celebrates the region's old "white gold" crop that once dominated the fields around the Catskills and welcomes farmers, local makers, and families for cauliflower dishes, tractor displays, numerous kids' activities, and music. During the festival, the tiny town feels significantly larger, and restaurants like Oda Wine Garden fill up fast.
The heart of summer has its own draw with the Margaretville Fire Department's Annual Field Days, a multi-night fair in Village Park with rides, live music, and fireworks lighting up the valley. When the festival crowds drift home, those who remain enjoy the riverside walkway downtown or head toward Dry Brook Ridge just outside the village for an easy taste of Catskills forest air.
Skaneateles
The small town of Skaneateles can be found at the very top of Skaneateles Lake, the cleanest of New York State's famous Finger Lakes. Aside from being one of the most beautiful little places in upstate New York, it is also one of the busiest. This is thanks to back-to-back annual events that welcome thousands of people each year. Skaneateles Festival (SkanFest) is a four-week music festival in the summer that attracts world-class performers to perform everything from Bach to bluegrass in a number of intimate spaces around town. Downtown's Genesee Street, in particular, becomes a corridor for connecting with festival guests and locals alike. For almost 50 years, the town has also hosted The Antique and Classic Boat Show at Clift Park in July. Exhibitors from all over the East Coast are welcome to show off their boats and meet others.
Winter flips the vibe into something a bit more theatrical. Dickens Christmas turns Skaneateles into a living storybook, with Ebenezer Scrooge, Bob Cratchit, and the Ghost of Christmas Present wandering the streets. There are horse-drawn carriage rides, roasted chestnuts, and basically everything you would want from a themed winter festival that runs every weekend from American Thanksgiving through Christmas.
Corning
Corning glitters along the Chemung River with a history shaped by fire, glass, and community spirit. Springtime brings GlassFest, a four-day celebration where live glassblowers turn molten art into masterpieces right in Centerway Square. Music, food vendors, and fireworks are also the draws here for both locals and visitors alike. All of whom can mingle in the open-air festival along Historic Market Street in the Gaffer District. HARVEST Fest welcomes fall with hayrides, live bands, and street dining.
Then there is Crystal City Christmas, the annual winter festival with numerous events such as the Parade of Lights and Sparkle celebrations that brighten Market Street and invite residents and guests to toast the season together.
Saranac Lake
Saranac Lake (not far from Lake Placid) sees its friendly personality come alive in its annual festivals. In August, PorchFest turns front porches into impromptu stages, letting neighbors play music while the rest of the village wanders from yard to yard, beer in hand, kids in tow. October brings the High Peaks Harvest Festival on Berkley Green, where local farms and makers showcase everything from homemade honey and baked goods to cider. Then there is the Winter Carnival, running from late January into February.
This may be the star event in Saranac Lake, as it draws crowds from all over to see its Ice Palace, parades, and snow sculptures. It is a mix of competition and playfulness that keeps the town connected and vibrant. This energy continues all year long with a banging Fourth of July celebration and various athletic competitions.
Canandaigua
The small upstate New York town of Canandaigua buzzes at the tip of its namesake lake, and you feel it the moment you hit the shore. On July 4th, Kershaw Park transforms into a block party with fireworks that launch over the water. It is one of the more popular events of the year, and the town goes all out for it. While the surrounding vineyards are wonderful places to hang out with friends during the summer, come October, the Ingle Vineyard Harvest Festival highlights Heron Hill wine in their tasting room.
Autumn also brings the Fall into Canandaigua event with pumpkin decorating, a parade, and other family-friendly activities. Then there is the Illuminate Light Parade in the winter with a ceremony for Santa's arrival and a lighting of the tree.
Cooperstown
Baseball is the heartbeat of Cooperstown. In many ways, the community is oriented around it. Every May, fans descend on the National Baseball Hall of Fame to celebrate the legends, plaques, and memorabilia that make the sport sacred here. Beyond the diamond, Lakefront Park on Otsego Lake hosts the weekly Summer Concert Series, where blankets, picnic baskets, and friends line the shore for free music under the sky.
Come July, the Independence Day celebration layers fireworks over the lake with a festival atmosphere that invites everyone to gather. Perhaps most notable is the Glimmerglass Festival, which runs through the summer, showcasing world-class opera and theater right on the lake's edge. Visitors and locals get to mingle in an intimate 918-seat theater in a town where the population isn't much larger.
Upstate New York's friendliest towns draw people together through annual events, festivals, and local attractions that appeal to almost every interest. From Saranac Lake's PorchFest and Winter Carnival to Canandaigua's Fall Into Canandaigua Festival, each gathering is centered on community and inviting people to be a part of it. While larger cities can get a bad rap for unfriendly atmospheres, New York State's littlest towns make up for it in spades. Whether you are looking to travel in the spring, summer, fall, or winter, each of these towns has an event ready to welcome you.
