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
In the wine-loving Finger Lakes region of New York, Naples is a quiet, picturesque town surrounded by natural beauty and plenty of opportunities for outdoor adventure, like hiking in Grimes Glen—a gorge with a creek running through the valley, with two stunning 60-foot waterfalls cascading down the walls and swirling swimming holes to soak in.
Renowned for its wineries and the annual Naples Grape Festival on September 28 and 29, 2024, Naples is a pretty town to mellow out in. Explore a few local wineries, like the well-known Hazlitt Red Cat Cellars, Arbor Hill Grapery & Winery, and Inspire Moore Winery, whose wines are names sentiments like Joy, Gratitude, Grace, and Harmony—all wineries on the Canandaigua Lake Wine Trail. In town, head over to Roots Cafe, located in a bright blue and purple house, for a Roots Burger stuffed with garlic butter; visit the Social Taproom & Restaurant for upscale casual dining and music in a vintage setting; or check out Cindy’s Grape Pies, a local institution.
Cooperstown
Despite its size, Cooperstown has a thriving art scene that rivals any big city. Of course, there is the world-famous National Baseball Hall of Fame & Museum, the hallowed home of America’s favorite pastime. There’s also the Fenimore Art Museum on the shores of Otsego Lake, on property once owned by famous “The Last of the Mohicans” novelist James Fenimore Cooper, the circa 1845 Farmer’s Museum, the Heroes of Baseball Wax Museum that features over 30 life-size wax figures of everyone from Babe Ruth to Marilyn Munroe, and many more. They do not call Cooperstown the “Village of Museums” for nothing.
After a day of museum touring, take a tour of another kind at the Ommegang Brewery. This brewery is renowned for its Belgian-style ales, inspired by traditional Belgian brewing techniques. Its famous Tap Room Restaurant has a fun, relaxed atmosphere perfect for Sunday Brunch Bingo or Fire Pit Fridays. From September 27 to 29, 2024, it hosts “Belgium Comes to Cooperstown 2024 (BCTC),” a weekend devoted to beer, music, food, and revelry.
Visiting these six upstate New York towns is the perfect way to unwind and rejuvenate, whether enjoying Woodstock’s mellow, artsy vibe or sipping something warm in one of Tivoli’s cozy cafés. Take a leisurely boat tour in Alexandria Bay, retreat into the past in Lewiston, enjoy wine tasting in Naples, or museum hop in America’s hometown, Cooperstown. The hardest part will be choosing only one laid-back spot to relax and enjoy the simpler things in life.
