Perhaps it’s because the Big Apple is the most-visited city in the United States, but when most people think of New York, they think of the New York City metro area in its southeastern corner. But the majority of New York’s land mass is north of the five boroughs of New York City.
Traveling north from the Big Apple toward the Great Lakes and mountain ranges that form the state’s borders, soaring skyscrapers and densely populated neighborhoods melt into clear lakes surrounded by fertile farmland and lush forests. Whether you’re visiting to ski, ice skate, or snowmobile in the winter or to canoe, hike, or attend a music festival in the summer, these are the quaint towns you won’t want to miss in New York State.
Note: Some New Yorkers consider everything north of the Bronx to be Upstate New York. Others consider Upstate to be everything north of Westchester County. I’m using the Westchester County definition.
About 70 miles southwest of the town of Woodstock, the Bethel Woods Center for the Arts now stands in the pasture where 500,000 people gathered in mid-August 1969. The Museum at Bethel Woods covers the 1960s and the cultural and social changes that gave rise to the historic music festival. And if you visit Bethel at the end of May, don’t miss Mountain Jam. This multiday, multistage event is held at the site of the original Woodstock and is the longest-running music and camping festival in the Northeast.
The three-day music festival that made this quaint Upstate NY town a household name back in 1969 actually took place on a dairy farm 70 miles southwest of Woodstock. But you can visit the Karma Triyana Dharmachakra Tibetan Buddhist Monastery for a different peace and music experience in Woodstock.
Chase waterfalls by hiking the mile-long trail to Kaaterskill Falls, browse the local shops and galleries, enjoy a live performance at the Bearsville Theater, or unwind at the Glo Spa. If you visit Woodstock in the summer, check out the Mower’s Saturday Market (also held on Sundays) and stop by Sunfrost Farms for a bite to eat or provisions to tide you over until your next stop in Upstate New York.
On the west bank of the Hudson River, Saugerties is a short drive from Woodstock and about 60 miles southwest of Albany. Here you’ll find the Woodstock Museum, full of memorabilia from the 1969 music festival.
Saugerties is also home to the Saugerties Lighthouse, a red-brick beacon more than 170 years old that sits on the end of a narrow peninsula that stretches out into the Hudson River. Take a docent-guided tour on a Sunday afternoon during the summer or spend the night in one of two second-floor bedrooms.
When you visit Saugerties, don’t miss Opus 40, known as the Stonehenge of North America; it’s surrounded by greenery and was inspired by ancient Mayan and Aztec architecture. Artist Harvey Fite created the impressive stone artwork in this abandoned quarry.
From fly-fishing to the highest, fastest, and longest zip line in North America, the Upstate New York town of Hunter offers plenty of outdoor adventure. For bird’s-eye views without the adrenaline rush, ride the six-passenger chairlift on Hunter Mountain instead.
Refuel after a day in the fresh mountain air with German fare at Jagerberg Beer Hall & Alpine Tavern. The schnitzel, sauerbraten, house-made spaetzle, and bratwurst just might trick your taste buds into believing you’ve been transported from the Catskills to the Alps!
5. Saratoga Springs
From thoroughbred horses to automobiles, several attractions in this Upstate New York city are related to the need for speed.
Start your visit with a trip to the National Museum of Racing to learn about three centuries of horse racing before visiting the Saratoga Race Course. If you prefer four wheels to four legs, then check out the Saratoga Automobile Museum. Housed in the beautifully restored plant that once bottled water from Saratoga’s natural mineral springs, this museum celebrates America’s love affair with cars.
For a slower-paced experience in Saratoga Springs, stroll through the Yaddo Gardens. Inspired by the Renaissance gardens planted in France and Italy, this idyllic green space features flowing fountains, fragrant roses, and a woodland rock garden. Or enjoy a tasting and live music at The Saratoga Winery.
6. Lake George
About 30 minutes north of Saratoga Springs, on the southern tip of the lake of the same name, is the town of Lake George in the Adirondacks. This town of 3,500 was the birthplace of the American vacation.
Not surprisingly, some of the most popular things to do in this quaint town in Upstate New York are tied to the 32-mile-long lake called the Queen of American Lakes. Summer is the most popular time to visit Lake George, when vacationers enjoy swimming, boating, and fishing. In winter, cold-weather lovers bundle up and flock to Lake George to ski, snowmobile, and ice fish.
If windshield time is more your thing, several scenic drives allow you to tour the area by car. For phenomenal views of the Adirondacks, drive the Prospect Mountain Veterans Memorial Highway. And for water views beyond Lake George, discover Lake Luzerne and more on this scenic drive.
7. Lake Placid
Along with Saint Moritz, Switzerland, and Innsbruck, Austria, Lake Placid is one of only a few destinations that have hosted the Winter Olympics more than once. Most Americans remember Lake Placid for the “Miracle on Ice,” when the American ice hockey team upset the Soviet Union’s team in 1980, ultimately winning the gold medal.
Because of the town’s tie to the Winter Olympics, history buffs won’t want to miss the Lake Placid Olympic Museum, located in the building where the American hockey team skillfully “shot the biscuit” into the net to win it all. You’ll see exhibits and artifacts celebrating the U.S. men’s hockey team of 1980. But you can also discover the history of speed skating and see how sleds have evolved over time.
Enjoy outdoor activities like kayaking, canoeing, or paddleboarding on Mirror Lake. There are also many beautiful places to hike in this peaceful small town in the Adirondacks. When hiking, watch for wildflowers like creamy white bloodroot, soft pink lady slipper, and bright red columbine. For more inspiration, read up on the best things to see and do in Lake Placid.
About an hour south of Buffalo, Ellicottville offers ski resorts in the winter and a canopy of shady trees in the summer. Golf enthusiasts can enjoy a golf getaway, including the 18-hole, par-70 double black diamond golf course at Holiday Valley. (Get a flyover of the course here.)
When you’re ready for a break, browse the shops, bars, and restaurants of the Ellicottville downtown area, being sure to pop into the Winery of Ellicottville to explore wines ranging from very dry to dessert. Or pair the pinot with the perfect piece of chocolate from Watson’s Chocolates just around the corner. Try the sponge candy, a Buffalo-area treat made from a mixture of corn syrup, sugar, and baking soda that’s dipped in chocolate.
9. Lily Dale
Less than 15 miles from the shores of Lake Erie, Lily Dale is a small town in Upstate New York known for its Spiritualist culture that has earned it the title of New York’s Seance Capital. Although the hamlet has less than 300 year-round residents, it welcomes nearly 100 times that in visitors each year as folks interested in the paranormal and New Age beliefs pilgrimage to Lily Dale.
Everyday mortals and skilled mediums can fuel up on caffeine and nourish their bodies at Lucy’s Coffee Shop in the heart of Lily Dale.
Located on a stretch of the Niagara River that connects Lake Ontario to Lake Erie, Lewiston has played several significant roles in American history. Stop by the church built in 1835 that now holds the Lewiston Museum to learn about the town that was the first European settlement in Western New York. Over the years, the town was the site of the first major battle of the War of 1812 and the final stop for American slaves seeking freedom in Canada.
Transition from history to science at the Niagara Power Project Visitors Center and discover the role the falls play in generating power.
Less than an hour south of Rochester, Canandaigua is located on the northern tip of the fingerlike Canandaigua Lake. Start your visit to this quaint Upstate New York town with a ride on the Canandaigua Lady, a double-decker paddle wheeler reminiscent of the steamboats that were a primary mode of transportation in the 19th century. Keep the Victorian Era vibe going by touring the Sonnenberg Gardens and Mansion State Historic Park. German for “sunny hill,” this 40-room Queen Anne mansion is surrounded by acres of gardens in continuous bloom from April through October. When you’re ready to return to the present day, head to the Canandaigua City Pier to walk along the water or relax and enjoy the scenic tranquility hundreds of miles from the non-stop hustle of New York City.
Fun Fact: Humphrey Bogart, the American actor well known for his role in Casablanca, spent his childhood summers away in a cottage on Canandaigua Lake.
12. Watkins Glen
While Upstate New York boasts many scenic spots, Watkins Glen State Park is truly magical. From rainbow-reflecting waterfalls to creeks packed with rainbow trout, it’s easy to want to search for a pot of gold as you wind along the park’s hiking trails. Or you can enjoy a completely different path — the Seneca Lake Wine Trail — sipping full-bodied pinot gris, fruit-forward Cabernet Franc, and sweet ice wines from the nearly 30 wineries that circle Lake Seneca. Watkins Glen is also home to a Formula One race track, farm sanctuary, and other interesting things to do and delicious places to eat.
Just as the Finger Lakes region has become a surrogate environment for the cold-weather grapes used to produce wine throughout Eastern Europe, the fertile soil along the northern tip of Skaneateles Lake is also home to another Eastern European crop: lavender. Just 30 minutes west of Syracuse, you’ll feel like you’ve stepped into a pastoral European postcard as you watch fuzzy lambs graze between rows of fragrant bushes at the Lockwood Lavender Farm. Or, if you need a break from the wineries in the Finger Lakes region, stop by the Last Shot Distillery tasting room adjacent to the Charlie Major Nature Trail. This small-batch distillery lovingly transforms locally grown corn, wheat, and other grains into smooth whiskey, vodka, gin, and liqueurs.
Located at the southernmost tip of Cayuga Lake, Ithaca is a charming town in the Finger Lakes Region. The area is dotted with gorges, waterfalls, and parks making it a great destination for outdoor enthusiasts. Get out on Cayuga Lake by renting a canoe, kayak, or paddleboard, or escape into nature with a scenic hike at Taughannock Falls State Park.
In addition to its natural attractions, Ithaca is home to Cornell University and a fun downtown area, Ithaca Commons, filled with quirky shops and delicious eateries. Foodies will love the chef-driven menu at Revelry Yards (try the yellowfin tuna tostada or a bowl of cioppino) and the signature burgers (try the NYS orchard burger) at The Ithaca Ale House.
And if you prefer wine to ale, you’re in luck. Ithaca is located on the Cayuga Lake Wine Trail. Six Mile Creek Winery & Distillery is on the eastern edge of Ithaca, and several other wineries line the west bank of the lake just north of town.
Pro Tip: Looking for more to do, see, and eat in Ithaca? Here’s how to spend a weekend in this college town.
Nestled around the southern tip of Otsego Lake, about halfway between Syracuse and Albany, Cooperstown is often a bucket-list destination for baseball fans. The National Baseball Hall of Fame and Museum is located here, and you’ll find America’s national pastime celebrated throughout this historic town.
Once you’ve had your fill of baseball, admire the unique views offered by the Glimmerglass Queen as she glides across Otsego Lake, or admire the painting, sculptures, and other impressive works at the Fenimore Art Museum.
Whether you’re immersing yourself in baseball history or drinking in the scenery, you’re sure to work up an appetite while exploring Cooperstown. At The Blue Mingo Grill, you can enjoy a bowl of New England clam chowder, share a platter of ahi tuna nachos, or dig into lump crab cakes while enjoying waterfront views. Here are several other scrumptious restaurants to check out in and around Cooperstown when you visit.
Located just 100 miles north of NYC, the picturesque town of Rhinebeck offers scenic views, rich history, and delicious restaurants. One of the best views of the Catskills in Rhinebeck is from Drayton Grant Park at Burger Hill, and history buffs will enjoy exploring Wilderstein. This impressive three-story Queen Anne mansion was the home of Daisy Suckley, a close confidant of America’s longest-serving president who was with FDR when he passed away.
When it comes to the best places to eat in Rhinebeck, I recommend the Smokin’ BLAT at Rhinebeck Bagels & Cafe for breakfast, a burger and fries at Buns Burgers for lunch, and dinner in a renovated 18th-century colonial home at The Amsterdam followed by a nightcap out back under the twinkle lights. Or visit the Rhinebeck Farmers’ Market to pick up provisions for a picnic.
17. Cold Spring
Located just north of the United States Military Academy in West Point, Cold Spring is home to the Hudson Highlands State Park Preserve. The preserve covers more than 7,400 acres along the east bank of the Hudson River, and it is a gorgeous place to enjoy the great outdoors. Admire the scenery and wildlife along the park’s hiking trails, including a section of the Appalachian Trail. Then, check out Magazzino Italian Art. In addition to gorgeous art installations, they have walking paths and an undeniably cute family of Sardinian donkeys living on the grounds!
Fuel up for a day of exploring Cold Spring with breakfast at Hudson Hil’s where they serve breakfast fare like farm-fresh eggs and stacks of pancakes all day. And be sure to enjoy a scoop (or two) of ice cream from Moo Moo’s Creamery before you leave.
From the Hudson Valley to the Finger Lakes, these charming towns in Upstate New York offer spectacular scenery, rich history, and delightful activities. Upstate New York has much to offer visitors all year long. For more to see and do in New York, see this page.