6 Most Laid-Back Small Towns in Upstate New York
Upstate New York is a haven for anyone looking for a laid-back and peaceful escape from the hustle and bustle of city life. From Woodstock's artistic vibes to Lewiston's historic charm to the serene shores of Alexandria Bay, small towns give visitors a chance to kick back, relax, and breathe a little easier. Whether exploring the scenic trails of the Catskills, enjoying a leisurely day by the water in the Thousand Islands, or indulging in the region's renowned wines and local cuisine, upstate New York has something for every kind of traveler who appreciates the slower pace and simpler pleasures of life.
Woodstock
Few towns symbolize a laid-back, carefree, and mellow lifestyle more than the small town of Woodstock, nestled in the iconic Catskill Mountains. Famous for its music festival history, originally called the Woodstock Music and Art Fair, the 4-day music festival in August of 1969 transformed Woodstock from a relatively unknown village into the artsy, relaxed community it is today.
When in Woodstock, why not head for the woods with a hike at Overlook Mountain? Visitors will find the trailhead about ten minutes outside town, and the out-and-back trail takes about three hours to finish, including time snapping photos from the multiple overlooks. At the top, there’s a fire tower with spectacular 360-degree views of the Catskills and the ruins of an old 1930s hotel to explore.
Back in town, visit Woodstock’s Tinker Street, once full of tie-dye t-shirts, incense, and head shops, now a mix of eclectic boutiques selling bohemian clothing and funky housewares, like Three Turtle Doves, Shop Little House, and Pacama Handmade. Other cool shops include Fruition Chocolate Works, Tinker Taco, and the independent bookstore Golden Notebook.
Tivoli
Tivoli is another small town with a relaxed bohemian vibe, about 50 miles south of New York’s state capital, Albany. With its proximity to the liberal arts college, Bard College, which is only a few minutes away by car, it has the relaxed pace of a college town with lots of cozy cafés, the Tivoli Artists Gallery (TAG), a few wine bars, and a popular whiskey pub called Traghaven. Stop in at Tivoli General or Tivoli Bread and Baking for a picnic-to-go, then head out to explore the surrounding Hudson Valley.
Spend a laid-back afternoon in Tivoli Bays—one of four Hudson River National Estuarine Research Reserve sites. The reserve is also part of the New York State Birding Trail that extends from Montauk to Buffalo and is home to over 450 species of birds. It encompasses over 1,700 acres of wetland, tidal marshes, upland areas with waterways and coves for kayaking and paddling, biking and hiking trails, fishing, and exceptional bird-watching opportunities.
Alexandria Bay
On the shores of the St. Lawrence River, Alexandria Bay is one of the most picturesque towns in the heart of the area known as the Thousand Islands. Sometimes, the best way to chill out is on the water. There is no shortage of things to do on the water, like booking a private boat tour with 1000 Island Scenic Boat Tours, where visitors can cruise past historic lighthouses like the Rock Island Lighthouse, waterfront mansions, or fairy-taled inspired castles like the 100-year-old Singer Castle on Dark Island or the 120-room Boldt Castle on Heart Island—a monument of love to the wife of the millionaire proprietor of the Waldorf Astoria Hotel.
Once the playground of the rich and famous, Alexandria Bay is now a family-friendly destination with activities like go-karting, mini-putt, and amusement at Alex Bay 500 Go-Karts. Grab a casual bite to eat on the waterfront at any one of the casual restaurants on the dock, like the Dockside Pub, Coleman’s Dock of the Bay, or Riley’s by the River.
Lewiston
Historic Lewiston is a quick 10-minute drive from Niagara Falls, with scenic views of the Niagara River and a laid-back community vibe. While Niagara Falls is one of the world’s most famous tourist destinations, attracting over 8 million tourists annually, visitors often choose to stay in nearby Lewiston for its quiet charm, excellent boutique shopping, and eateries like Orange Cat Coffee Co. or Silo Restaurant, famous for its “Haystack” sandwich. Wander through the Earl W. Brydges Artpark, a 150-acre outdoor venue for live theater, performances, and concerts in a family-friendly setting.
Walk back in time in Lewiston, which was home to the first major battle of the War of 1812, as well as the final stop on the Underground Railroad—the secret network of routes and safe houses used by enslaved African Americans in the United States to escape to Canada. Visit landmarks associated with the Underground Railroad, like the Freedom Crossing Monument on the river, the Tuscarora Heroes Monument, and the Lewiston Museum, built as St. Paul’s Episcopal Church in 1835.
Naples
Nestled in the wine-loving Finger Lakes region of New York, Naples is a peaceful, charming town embraced by stunning natural scenery and abundant outdoor adventures. Imagine hiking in Grimes Glen, a picturesque gorge with a gentle creek winding through, featuring two breathtaking 60-foot waterfalls and inviting swimming holes perfect for a dip. Famous for its lively wineries and the lively Naples Grape Festival, this town offers a lovely escape to unwind.
Take a leisurely visit to local vineyards like Hazlitt Red Cat Cellars, Arbor Hill Grapery & Winery, and Inspire Moore Winery, where wines carry heartfelt names like Joy, Gratitude, Grace, and Harmony—all part of the scenic Canandaigua Lake Wine Trail. When you're in town, stop by Roots Cafe in a cheerful blue and purple house for a delicious Roots Burger drizzled with garlic butter. For a cozy dining experience with music and a vintage vibe, the Social Taproom & Restaurant is a great choice. Don't miss Cindy’s Grape Pies, a beloved local gem that’s been delighting visitors for years.
Cooperstown
Despite its charming size, Cooperstown boasts a vibrant art scene that can rival any big city. Of course, it’s home to the world-famous National Baseball Hall of Fame & Museum, the revered center of America’s favorite pastime. Visitors can also explore the Fenimore Art Museum located on the scenic shores of Otsego Lake, once a property owned by the renowned novelist James Fenimore Cooper, author of "The Last of the Mohicans." Plus, there’s the circa 1845 Farmer’s Museum, the Heroes of Baseball Wax Museum with over 30 lifelike wax figures of icons from Babe Ruth to Marilyn Monroe, and many more attractions. No wonder Cooperstown is affectionately called the “Village of Museums.”
After a day filled with exploring these wonderful spots, why not switch gears and enjoy a visit to Ommegang Brewery? Known for its delicious Belgian-style ales crafted with traditional techniques, the brewery’s Tap Room Restaurant offers a warm, friendly atmosphere, perfect for enjoying Sunday Brunch Bingo or Fire Pit Fridays with friends.
Visiting these six upstate New York towns offers a great way to unwind and refresh, whether you’re soaking up Woodstock’s relaxed, artsy atmosphere or enjoying a warm drink in one of Tivoli’s charming cafés. Take a leisurely boat ride in Alexandria Bay, step back in time in Lewiston, indulge in wine tasting in Naples, or explore museums in Cooperstown, known as America’s hometown. The only challenging part will be selecting just one peaceful spot to relax and savor the simpler pleasures of life.
