12 Lesser-Known (but Totally Charming) Upstate New York Towns You Need to Visit

While Cooperstown is a little outside our ideal distance-from-the-city radius, it’s very much worth the four-hour-plus trek. You’ll feel like you’ve stepped into a Norman Rockwell painting when you visit this quaint all-American town, most famous for being the home of the National Baseball Hall of Fame (now open with COVID-19 precautions in place—read more here). Expect your bed-and-breakfasts to be decorated in florals and your meals to be hearty. Speaking of food, don’t miss the authentic Italian fare at Bocca Osteria or getting your caffeine fix at the charming Stage Coach coffee shop.

Where to stay: 

• Cooperstown Beautiful Modern Home (6 guests): $376/night
• Stunning Home Short Drive from Cooperstown (6 guests): $143/night
• Newer Country Home In Scenic Setting (4 guests): $260/night

The journey to Narrowsburg, a picturesque town between the Catskills and Poconos, is half the fun, since it includes traveling along the scenic Hawk’s Nest, a stretch of winding road along the Delaware River. Though small in size, the Main Street is mighty in what it has to offer—such as the Heron, easily one of the best restaurants in the region.

Where to stay:

• Lakefront House with Private Dock (6 guests): $226/night
  
• Cozy Home in the Mountains (6 guests): $163/night
• Riverfront Million Dollar Mountain View Estate (6 guests): $302/night

Nestled in the foothills of the Berkshires and located along the Appalachian Trail, Pawling was once a haven for reticent celebrities: With its large properties and quaint village, it’s no wonder they found respite here. Now a new wave of city dwellers is flocking, in part because of the easy commute (it’s less than 90 minutes on Metro North from Grand Central) and also because of the vast array of outdoor activities available here such as horseback riding, hiking and swimming. Local favorite McKinney & Doyle is the best brunch spot in town and is currently offering indoor dining and takeout, while Daryl’s House is the place to be on a Friday night for live music and great brews.

Where to stay: 

• Three-Bedroom Cabin in Private Candlewood Lake Community (6 guests): $243/night
• Direct Water Front Home (6 guests): $552/night
• Millbrook Country Dream (5 guests): $728/night

For tea lovers, a visit to Millerton is a must. Stop by Harney & Sons’ flagship store to stock up on your favorite teas (we’re currently obsessed with the chocolate-coconut Soho blend). But even if tea isn’t, well, your cup of tea, there’s still plenty to do here, such as antiquing and cycling. Millerton is at the north end of a recently restored bike route, the Harlem Valley Trail, which is paved and shaded by trees and extends south to Wassaic—another town worth visiting (more on that below). After enjoying the Great Outdoors, enjoy a relaxing meal and a flight of wines at 52 Main, a charming spot that’s known for tasty tapas.

Where to stay: 

• Mountaintop Retreat (2 bedrooms): $259/night
• Enchanting Luxury Country Estate (10 guests): $1,125/night
• Charming Cottage (2 guests): $280/night

This onetime cement-manufacturing town is now home to a thriving community of artists and entrepreneurs. One of the best ways to take in the colorful buildings of Main Street (home to delightful vegetarian cafés, artists’ studios, bookshops and kitschy vintage shops) is from above: The Rosendale Trestle, a 940-foot continuous bridge and former railroad trestle, offers breathtaking views of Rosendale Village and Rondout Creek. Travelers rave about Egg’s Nest for tasty vegetarian and vegan fare as well as the Alternative Baker, a cute bakery that’s famous for its lemon cakes.

Where to stay: 

• Imagine Woodstock Field Studio (3 guests): $88/night
• Luxe Mountainside Retreat (3 guests): $304/night
• Beautiful Farmhouse (10 guests): $336/night

Wassaic, the last stop on the Harlem Line, is a dream for people who love to explore relics from a past era. If you’re with a group, rent out the historic Salvato Mill. Be sure to scope out the ruins of 19th-century charcoal kilns and pay a visit to Hunter Bee, which sells everything from fine antiques to quirky oddities. Keeping with the nostalgia theme, eschew modern transportation once you’ve arrived and explore the area by bicycle—including the Kings Highway Cider Shack that offers great ambiance and outdoor eats in the warmer months. Finally, end your night with a double feature at the Four Brothers Drive-In, one of the last of its kind in neighboring Amenia.

Where to stay: 

• Nature Lover’s Mountaintop Retreat (2 guests): $259/night
• Beautifully Restored 1840 Colonial Farmhouse (11 guests): $274/night
• Lake House in Woods (10 guests): $1,000/night

Stone Ridge, a historic hamlet in the town of Marbletown, is known for its romantic, centuries-old homes, winding roads and bucolic farmland. Dutch stone houses are plentiful here; the most famous one in the area is the meticulously restored Hasbrouck House. Even if you don’t book one of its 17 rooms, be sure to stop by Butterfield for an unforgettable and supremely tasty dinner. Or pick up your own locally grown foods at the Stone Ridge Orchard and Davenport Farms, and treat yourself to a home-cooked meal.

Where to stay: 

• Hudson Valley Retreat (10 guests): $1,801/night
• Secluded Home with Fireplace (5 guests): $283/night
• State of the Art Log Cabin (6 guests): $338/night

As you approach this Hudson River village in Westchester, you are greeted by a stunning arch bridge passing over a flowing dam which will immediately set the tone for your visit—a beautiful and serene escape. Popular attractions in Croton-on-Hudson include Croton Gorge Park, 97 gorgeous acres complete with a beach, nature trails and a pretty pavilion; Van Cortlandt Manor, the 18th-century stone house and brick ferry house of New York’s famous Van Cortlandt family; and Croton Gorge, the historic New Croton Dam set high above the town that’s the perfect picnicking spot. When it comes to good eats, Croton Tapsmith is a local favorite offering cold brews from nearby Hudson Valley producers and locally sourced food options as well as The Blue Pig for dessert—including the best Oreo ice cream you’ve ever tasted.

Where to stay: 

• Private Lake Escape (4 guests): $375/night
• Magnificent Mini-Estate (10 guests): $814/night
• Beautiful Private House (4 guests): $594/night

Part of the town of Red Hook, this sleepy village has a population of just over 1,000 people and spans less than two miles. But don’t let its size fool you—there are plenty of hip new businesses and creative outlets here, providing visitors with ample things to do for a weekend trip upstate. After a hike in the area or kayak ride along the Hudson, treat yourself to a cone at Fortunes ice cream shop or a drink at Traghaven, the hipster-y Irish pub with a serious whiskey selection. If you’re staying for longer than a day trip, stock up on supplies at the highly-Instagrammable general store.

Where to stay: 

• Cozy House (5 guests): $228/night
• Hudson Valley Cottage Farmstay (4 guests): $378/night
• Chalet in the Woods (6 guests): $300/night

This historic town on the north shore of Skaneateles Lake has less than 3,000 residents but you’d never know it. How so? The excellent restaurants rival some of NYC’s finest, there’s an award-winning spa, a can’t-miss winery, multiple accommodation options including a 4-star resort, tour boat cruises, art galleries, a historical and boat museum and great shopping—all within walking distance of the lake. Skaneateles Bakery is your go-to spot for sandwiches and pastries while Blue Water Grill boasts gorgeous lake views and mouthwatering crab cakes. After a day of exploring, kick back with a local brew at Finger Lakes on Tap.

Where to stay: 

• Newly Remodeled Home Near Owasco Lake (8 guests): $220/night
• Unique Duplex at Heron Point (8 guests): $380/night
• Beautiful Lake Home with an Amazing View (10 guests): $393/night

Unsurprisingly for a town that holds a spot on the National Register of Historic Places, Cold Spring in Putnam County oozes charm and quaintness. Here you’ll find boatloads of beautifully preserved 19th-century buildings, independent shops and sweet bed and breakfasts. Speaking of boats, don’t miss cruising along the Hudson while you’re here—it’s a popular pastime along with hiking, biking and golfing. With a river view and a pavilion, Hudson House is a great option for lunch or dinner (get the lobster bisque) followed by a trip to Moo Moo’s Creamery for dessert.

Where to stay: 

• Beautiful Home with Glorious View (9 guests): $429/night
• Charming Guest State House (4 guests): $123/night
• Beautiful Secluded Country Cottage (8 guests): $600/night

This Adirondack Mountains gem was recently listed in US News & World Report as one of the “6 Forgotten Vacation Spots” in North America...and it’s time we get reacquainted. Founded in the 19th century, this Essex County village boasts small-town charm and pristine natural beauty. The main draw here is the beautiful surroundings where visitors like to ski, hike, bike and unplug from the stresses of modern life. And what better way to relax than with some delicious eats? The View Restaurant in Mirror Lake Inn resort and spa boasts seriously stunning vistas in addition to elegant comfort foods and an extensive wine list. For something a little more casual, try Smoke Signals, the BBQ joint that’s know for its friendly service and mouthwatering meats.

Where to stay:

• Newly Renovated Private Camp On Lake Placid (14 guests): $1,714/night
• The Hut on Grandview in Lake Placid (5 guests): $233/night
• Spectacular Lake Placid Village Home (10 guests): $819/night