7 Underappreciated Towns to Visit in Upstate New York

When people think of New York State, many consider places like the five boroughs, Rochester, Syracuse, Buffalo, and the majesty of the Adirondacks and Niagara Falls. It's not that smaller towns are overlooked or have nothing to offer. In many cases, upstate New York towns aren’t in the conversation because most people know very little about them, their communities, their unique character, and their vibrant atmosphere.

Pawling

On state route 22 due north of New York City at the eastern edge of the state, Pawling rests in the Hudson Valley with gorgeous views of the Appalachian Trail. The eastern Duchess County village is a restful haven for outdoor enthusiasts hoping to catch a fish or two, ride horses, or take a hike along its many trails, especially during the autumn.

Enchant your inner foodie, enjoy some retail therapy, and partake in the many events held throughout the year. Pawling Bread Company excites the senses, creating new and delicious pastries daily, then head to “The Strip” to pick up a souvenir from one or more of the eclectic shops down Main Street. In the evening, head to Daryl’s House Club, a venue owned by Daryl Hall of Hall and Oats.

Rosendale

Centered between New York City and Albany and right off Interstate 87, Rosendale is the quintessential upstate town, with all the stunning views, lush forests, and rich history many have come to admire. From the Historic Rail Trail to the serenity of the lush topography, this isn’t a town anyone should overlook. Especially, if you have a sense of adventure.

What type of adventure, you might ask. That depends on if you are afraid of heights. One of Rosendale’s biggest attractions is the Rosendale Trestle Bridge, an out-of-service train bridge, converted to a pedestrian and bike path. At 150 feet high and 940 feet long, all who are brave enough will gaze upon magnificent views of the town and surrounding areas, and take some incredible pictures.

Hunter

In the Great Northern Catskills, Hunter has a very interesting distinction for its unique duality. The town of Hunter is made up of two villages, Hunter and Tannersville, each with their own individual attractions but all under the same geographic umbrella. This concept might seem confusing but think of it like getting two town experiences in one visit.

In the winter, Hunter Mountain Resort draws the most avid skiers from all over the state to shred its powder and is very family-friendly. After the snow melts and the weather warms a bit, the mountain opens to trails leading to the top, hikers getting a birds-eye-view from the intense 3200-foot summit. You are sure to work up a thirst. Quench it at Hunter Mountain Brewery with craft beers and tasty fare.

Delhi

Two hours west of Albany comfortably nestled in the Catskills, this remote town is your destination for a quiet space if the working world has just become too much. It is home to SUNY, the local college, the West branch of the Delaware River, and an almost endless expanse of rolling hills and forests.

Take a weekend trip and bring the whole family to the Taste of the Catskills festival in October. The event is family-friendly and showcases food, beer, and crafts of the area, including information about how the farm-to-fork movement actually works. Delhi has a rich history dating back to the 1800s, all available to you in the Delhi Historical Society.

Dunkirk

Just off Interstate 90 on the far western side of New York and resting on the banks of Lake Eerie, Dunkirk is a town for not just history buffs, but also anyone who loves lighthouses. The Dunkirk Lighthouse and Veterans Park Museum tells of the significance the beacon had in guiding ships traversing Lake Eerie into Dunkirk Harbor.

During the warmer months, Gratiot Beach awaits for swimming, biking, and picnics while delighting in the impressive scale of Lake Erie. It might be one of the smaller of the Great Lakes, but it still poses an imposing stature. No visit is complete without strolling down Dunkirk Boardwalk Market, with shops, restaurants, and more, all within view of the lake.

Owego

With Pennsylvania due south, the Susquehanna River forming its southern border, and the Finger Lakes only a short hop away, this is your ultimate base camp if taking in this part of Upstate New York is your plan for a weekend getaway. Some would call Owego a sleepy town where the clock moves a little bit slower, but that isn’t necessarily a bad thing. Not when you have so many stunning views and peaceful environments to enjoy.

Grab a paperback at Riverrow Bookshop and hit the Riverwalk, settling in a comfy spot, perhaps with a snack from Las Chicas Taqueria. Tacos, a good read, and the sounds of the water flowing nearby. For some excitement, mosey into Tioga Downs Casino where you can try your luck with slots, table games, and even bet on the ponies. For true nature lovers, don’t miss Waverly Glen, home to the majestic Waverly Glen Waterfall.

Massena

Between the Grass River and Raquette River at the Northern border of the state, Massena gets much of its history from its proximity to the St. Lawrence Seaway. Enthusiasts of all things nautical can learn all about it at Eisenhower Lock, where ships, great and small, have traversed these waters for hundreds of years.

Get a tan, take a swim, do some boating, and revel in the bliss as kids and adults alike splash and play at Robert Moses State Park or Massena Town Beach, both on the St. Lawrence River. There are so few true drive-in movie theaters left in the US, so maybe take in a film at 56 Auto Drive-in Theater and let your kids experience what many of us grew up enjoying. Plan on Italian for dinner at An Italian Affair, a very popular restaurant serving, you guessed it, authentic Italian food.