In the days of social distancing, travelers are looking for places to visit and stay without crowds. Popular travel sites like Airbnb saw an influx of both travelers and remote workers heading to Upstate New York looking to get away from it all. Now, national publication TRAVEL + LEISURE has named the best small towns in New York worth a visit.
Whether it be a place full of small town charm or one of Upstate New York’s peaceful countrysides, here are the towns with fewer than 10,000 residents on their list.
Amenia (Dutchess County)
Small in population, but big in history, the town of Amenia near the Connecticut border made the list for its old architecture, antique shops, and zen-inspiring views, according to T+L. Amenia is along the growing Harlem Valley Rail Trail which runs 26 miles from the hamlet of Wassaic to Copake Falls, one of several rail trails in Upstate New York.
You can also plan a stay at nearby Troutbeck, a historic mansion-turned hotel and restaurant. Built in 1919 as a private estate, it features a 17-room manor house, a 12-room annex, and four-bedroom lodge and garden house structures. Its historic guest list boasts names like Mark Twain, Teddy Roosevelt, W.E.B. DuBois, and Thurgood Marshall.
Livingston Manor (Sullivan County)
This hamlet is located in the Borscht Belt, which once served as a vacation destination for Jewish patrons when other resorts and hotels discriminated them. T&L sites the town’s recent hotel and restaurant boom as a draw to this quaint Catskills town. The magazine also named the area one of America’s top 10 “must visit” places in 2021.
While you’re in Livingston Manor, stop by the Catskill Fly Fishing Center and Museum and go fishing in neighboring Roscoe, NY which bills itself as “Trout Town USA.” You can also travel over one of the oldest covered bridges in New York state.
Need a bite to eat? Check out neighborhood landmark, Robin Hood Diner which made its way onto our semifinalist list in our Upstate New York’s best diner list.
Mount Tremper (Ulster County)
Head east from Livingston Manor and you’ll find yourself in Mount Tremper. Located within the Catskill Mountain park, this hamlet gets high marks from T&L for hiking, local shops, and delicious eateries and farm stands.
If you’re planning on hiking Mount Tremper’s namesake mountain or if you’d just like to enjoy the view, head to the beloved Phoenicia Diner, which has made several of our best diner lists over the years. Order up a bagel topped with locally smoked trout or house-cured corned beef hash and wash it all down with a local bourbon milkshake.
One of Mount Tremper’s most unique attractions may be the Kaatskill Kaleidescope, otherwise known as the world’s largest kaleidoscope, located at Emerson Resort & Spa. Housed in a 56-foot silo, it is a truly unique psychedelic visual and sound experience.
Saranac Lake (Franklin and Essex County)
Head north to the Adirondack Park to visit the famed mountain town of Saranac Lake. Known as “Adirondacks’ Coolest Place” (and the nation, with its chilling winter temps), this town is fun to visit year round with its family-friendly Saranac Lake 6er hike challenge, the hand-carved Adirondack Carousel, renowned Winter Carnival, and its proximity to Olympic history in Lake Placid.
Other notable places to stop in Saranac Lake are the Robert Louis Stevenson memorial cottage, the Saranac Islands, Hotel Saranac, and on your way out of town, grab an ice cream cone from Donnelly’s.
Lake George (Warren and Essex County)
Continue on in the Adirondack Park to Lake George, located close to the Vermont border, where TRAVEL + LEISURE said offers major vintage appeal and pristine lakeside wilderness. It is true that this small town has had its fair share of historic visitors and can best be described by President Thomas Jefferson who said, “Lake George is, without comparison, the most beautiful water I ever saw. Formed by a contour of mountains into a basin… finely interspersed with islands, its water limpid as crystal, and the mountain sides covered with rich groves.”
Whether you are basking on Million Dollar Beach, boning up on your history at the Fort William History Museum, zipping around on a Six Flags Great Escape roller coaster, parasailing over Lake George, or trying to figure out how the Lake George mystery spot works, there is no shortage of activities for every kind of traveler.
High Falls (Ulster County)
Just north of the Mohonk Preserve lies High Falls, NY, population 627 at the 2010 census. Travel + Lei
sure said its proximity to New York City makes it a perfect getaway from big city lights. Travel to the nearby Shawgunk Mountains, otherwise known as “The ‘Gunks” and take in the preserves where there are more trails, cliffs, swimming holes and waterfalls than just about any other place in Upstate New York.
T+L also highlights a trip to High Falls’ Woodstock Farm Sanctuary where you can visit the animals which became celebrities in their own right during the coronavirus pandemic when you could hire them to “goat bomb” one of the endless Zoom calls people were experiencing at the height of social distancing.
Skaneateles (Onondaga County)
Located in Central New York, Skaneateles takes its lake life seriously with its beautiful turquoise blue waters and small town charm. T+L said the area’s boating, hiking, antiquing, and wine tasting at local vineyards could fill a week’s vacation. For all of this and more, Skaneateles has previously made our list of Upstate New York’s best four-season towns as it’s a great place at any time of year.
Make sure to hit favorite local eateries like the historic Sherwood Inn, Doug’s Fish Fry, and follow the your nose to freshly made donuts at the Skaneateles Bakery. Looking for a place to head with your girlfriends? The village also has all the elements of a perfect girls’ weekend.
Trumansburg (Tompkins County)
Heading deeper into Finger Lakes country, Trumansburg is bursting with good hikes and good eats. T+L hits the biggest highlights in this area. They include Taughannock Falls State Park, featuring the highest single-drop waterfall east of the Rocky Mountains and the Finger Lakes National Forest, New York’s only National Forest, from which you can hike the Finger Lakes Trail which extends to 560 miles in its entirety.
Once you’ve worked up an appetite whether it be on a gorge trail or along the nearby Cayuga Lake Wine Trail, check out Trumansburg’s growing food scene, be it the upscale Inn at Taughannock Falls or more low-key Atlas Bowl, a throwback bowling alley with a modern menu.
Pine Plains (Dutchess County)
Nestled between Red Hook and the Connecticut border, Pine Plains is a small community with a walkable charming town center. Hike to the top of the Stissing Mountain Fire Tower, or lay low and enjoy hiking forest trails around Stissing Pond and Thompson Pond Preserve, part of the Nature Conservancy.
When in town, make sure to order yourself up some lunch, or maybe just a big slice of cake from Pine Plains Platter which made a previous list of Upstate New York’s sweetest dessert spots, according to Yelp.
Chatham (Colombia County)
Chatham, which was first called Groat’s Corners, is a little town less than an hour away from the Berkshires. T+L names Chatham to the list for its little slice of Americana with farmlands and canned preserves galore.
While you’re there, stop into one of its many shops like Bimi’s Cheese Shop, the Chatham Bookstore, or American Pie, a self proclaimed “quirky little place” with everything from gifts to home goods. Need a bite to eat and a cold drink to wash it down? Visit The People’s Pub, a once dive-bar, turned farm-to-table restaurant with a menu that changes with the seasons and local supplies.
Don’t miss a visit to Chatham resident Roy Kanwit whose giant sculptures adorn the nearby Taconic Sculpture Park and Gallery. Kanwit also allows those interested to explore the sculptures on his property too, by appointment.
Penn Yan (Yates County)
On the western side of the Finger Lakes lies Penn Yan at the northern tip of Keuka Lake. T+L reports that the main street looks like something out of a fairytale. This lakeside country town named for its early Pennsylvania and Yankee settlers is bursting at the seams with outdoor activity.
Make sure to visit the seasonal Windmill Farm and Craft Market, one of the Finger Lakes’ major tourist destinations with more than 100,000 visitors each year. It’s a great place to buy Amish and Mennonite goods as well.
If you’re in town during cider doughnut season, visit Wager’s Cider Mill for some freshly made sweet treats. And if that sweet tooth still isn’t satisfied, don’t sleep on the corn fritter sundae at Seneca Farms. The roadside restaurant made our list of finalists for best ice cream in Upstate New York in 2017 with good reason.
You’ll also want to check out the World’s Largest Pancake Griddle, that yes, made the world’s pancake in 1987 at the town’s Buckwheat Festival.
Narrowsburg (Sullivan County)
Home to the often photographed “Hawk’s Nest Drive” twisting along the Delaware River on NY-97, Narrowsburg sits on the New York-Pennsylvania border. You’ll also get views of other birds of prey as this hamlet is also a great spot for spotting bald eagles during winter, according to Audobon New York.
The main street of this Catskills town is packed with shops and restaurants, including Nest, a lifestyle boutique opened by a former Vogue editor, and the clothing boutique, Mayer Wasner.
If you’re looking to take in the country views, embark on a scenic drive 50 miles north to the Rocky Mountain-like town of Callicoon and visit its namesake brewing company for an enjoyable Sunday drive in Upstate New York.
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