13 Under-the-Radar (but Totally Charming) Upstate New York Towns You Need to Visit

• Why We Love It: quintessential small-town feel, interesting museums, close to the lake
• Things to Do: National Baseball Hall of Fame; Bocca Osteria; Fenimore Art Museum
• Where to Stay: The Otesaga Resort Hotel (from $120/night); Landmark Inn (from $214/night); The White House Inn (from $160/night)

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. 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. And if you enjoy museums, be sure to spend some time at Fenimore Art Museum, housed in a neo-Georgian mansion, and The Farmer’s Museum.

• Why We Love It: by the sprawling Delaware river, good variety of museums, good culinary scene
• Things to Do: Hawk’s Nest; The Heron; Fort Delaware Museum
• Where to Stay: The Maisonette (from $225/night, sleeps 4); Narrowsburg Mountain Retreat (from $2,970/night, sleeps 16+); Historic School House Cottage (from $213/night, sleeps 4)

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, the Main Street is mighty in what it has to offer—such as The Heron, easily one of the best restaurants in the region. Meanwhile, Art connoisseurs will appreciate the Delaware Valley Arts Alliance and River Gallery, while outdoorsy types will want to hit the Fort Delaware Museum and Upper Delaware River for scenic views.

• Why We Love It: easy access from NYC, plethora of outdoor activities
• Things to Do: horseback riding; brunch at McKinney & Doyle;
• Where to Stay: Station Inn (from $279/night); Hobbit House (from $500/night, sleeps 6); Pawling Retreat (from $398/night, sleeps 12)

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 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 (you need an order of the strawberry cream cheese pancakes, stat), while Daryl’s House is the place to be on a Friday night for live music and great brews.

• Why We Love It: fun food scene, great outdoor activities
• Things to Do: Harney & Sons flagship store; cycling on the Harlem Valley Trail; tapas at 52 Main
• Where to Stay: Fairfield Inn & Suites (from $239/night); Interlaken Inn (from $269/night); Troutbeck (from $593/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 dragon pearl jasmine tea). 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.

• Why We Love It: beautiful scenery, plenty of culture and art activities, good food
• Things to Do: Vanderbilt Mansion; Mohonk Preserve; Hudson River walkway 
• Where to Stay: Hasbrouck House (from $410/night); ElmRock Inn Bed & Breakfast (from $220/night); Mohonk Mountain House (from $861/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 is to stroll on Main Street. First stop: Postmark Books to pick up a tome and a bouquet from the in-house florist. Then, check out the Women’s Studio Workshop to see the latest gallery exhibition. Seeking some grandeur in the countryside? The Vanderbilt Mansion is a must-see. And for those who love the views, The Rosendale Trestle can’t be missed. It’s a 940-foot continuous bridge and former railroad trestle that offers breathtaking views of Rosendale Village and Rondout Creek. Mohonk Preserve and the walkway over the Hudson also don’t disappoint. On your way home, swing by the Alternative Baker, a cute bakery that’s famous for its lemon cakes.

• Why We Love It: old-timey feel, including historic sites, antiques and a drive-in
• Things to Do: see the charcoal kilns; shop at Hunter Bee; have a drink at Kings Highway Cider Shack
• Where to Stay: Cozy Hudson Valley House (from $350/night, sleeps 6); The Red Country Cottage (from $167/night, sleeps 8); 1976 Shasta Camper (from $131/night, sleeps 2)

Wassaic, the last stop on the Meto-North 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.

• Why We Love It: romantic architecture, bucolic landscapes, local food scene
• Things to Do: dinner at Butterfield, picnic supplies at Stone Ridge Orchard
• Where to Stay: Longview Farm (from $917/night, sleeps 10); Modern Mountain House (from $329/night, sleeps 8); Historic Stone Ridge Apartment (from $106/night, sleeps 2)

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 foran unforgettable and supremely tasty dinner. Or pick up your own locally grown foods at the Stone Ridge Orchard and treat yourself to a home-cooked meal.

• Why We Love It: serene city escape, plenty of outdoor activities, vibrant local food scene
• Things to Do: Croton Gorge Park, Van Cortlandt Manor, dessert at The Blue Pig
• Where to Stay: The Abbey Inn & Spa (from $478/night); Casa Hudson (from $170/night); Inn on the Hudson (from $159/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. 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.

• Why We Love It: super walkable, outdoor activities, art scene
• Things to Do: hike or kayak along the river; Tivoli General Store; cone at Fortunes Ice Cream
• Where to Stay: Central House Inn (from $282/night); Morning Glory Bed & Breakfast (from $232/night); Hudson Valley Getaway (from $238/night, sleeps 6)

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.

• Why We Love It: vibrant local food scene, walking distance of the lake, museums and cruises
• Things to Do: dine at Blue Water Grill; wine tasting at Anyela’s Vineyards; spa day at Mirbeau Inn & Spa
• Where to Stay: 34 State Luxury Suites (from $542/night); The Bond 1835 (from $171/night); Skaneateles Lakeside Retreat (from $405/night, sleeps 4)

This historic town on the north shore of Skaneateles Lake has less than 3,000 residents but you’d never know it. Book yourself a spa appointment at the refined Mirbeau Inn & Spa and then head to a wine tasting at Anyela’s Vineyards. Tour boat cruises are a great way to admire the lake views, while the Historical Society hosts exhibitions featuring the region’s history. Not to mention the various art galleries and great shopping within walking distance to the lake. And when you find yourself needing a nibble, Skaneateles Bakery is your go-to spot for sandwiches and pastries. Blue Water Grill is another local watering hole boasting gorgeous lake views and mouthwatering crab cakes.

• Why We Love It: 19^th-century architecture, unique local businesses, river views
• Things to Do: river cruises; Hudson Highlands State Park; Storm King Art Center
• Where to Stay: Cold Spring Cottage (from $242/night, sleeps 5); Cold Spring Loft (from $195/night, sleeps 4); Hilltop Hideaway (from $400/night, sleeps 14)

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. 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. Be sure to explore Hudson Highlands State Park for sweeping views and spend an afternoon at the Storm King Art Center, known for its vast collection of outdoor sculptures.

• Why We Love It: small-town charm, bucolic green spaces, great outdoor activities
• Things to Do: outdoor activities (skiing, hiking, cycling, season dependent); dinner with a view at Mirror Lake Inn; Lake Placid Olympic Museum
• Where to Stay: Golden Arrow Lakeside Resort (from $176/night); Mirror Lake Inn Resort & Spa (from $366/night); Jay A-Frame Cabin (from $350/night, sleeps 6)

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 the Olympic museum and complex.) And what better way to relax than with some delicious eats? The View Restaurant in Mirror Lake Inn 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 known for its friendly service and mouthwatering meats.

• Why We Love It: larger town with village charm, art and culture hub
• Things to Do: National Museum of Racing, Saratoga Performing Arts Center, Saratoga Automobile Museum
• Where to Stay: Saratoga Arms Hotel (from $446/night); Union Gables Inn (from $262/night); Saratoga Casino Hotel (from $238/night)

With a population of 28,000, Saratoga has the small-town charm while being an arts, culture and sports powerhouse. It’s a hub for thoroughbred racing, so a visit to the National Museum of Racing and Hall of Fame is a no-brainer. (If it’s the season, get yourself down the racecourse, too.) Live music fans will want to catch a show at the Saratoga Performing Arts center, which regularly hosts classical, jazz, pop and rock concerts in the summer. And for those who love cars, the Saratoga Automobile Museum is a thrilling way to spend an afternoon.