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



Slide 1 of 7: 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. Where to stay: How does having an entire chalet to yourself sound? This camping cottage located in nearby Cherry Valley can fit up to four guests and boasts an impressive array of activities on the grounds including tennis, basketball, minigolf, non motorized boating, a beach and more. (Just make sure to double check which activities are currently available before you book.) RELATED: 7 Artsy Day Trips Every Culture-Loving New Yorker Needs to Take
Slide 2 of 7: 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 that’s now open for online orders and curbside pickup. Where to stay: Sit back and relax at the Little House in the Flats that’s located across the street from the Delaware River and just a short walk to Narrowburg’s main street. After a day of hitting the trails, fire up the gas grill and unwind with a glass of wine on the wrap-around porch.
Slide 3 of 7: 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. Where to stay: Sleep under the stars in the Moon Lodge Yurt that can accommodate up to three guests and is equipped with a wood-burning stove, outdoor shower and fire pit.
Slide 4 of 7: 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. Where to stay: This two-bedroom cabin comes complete with river views and easy access to fishing and the Appalachian Trail.

Slide 5 of 7: 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. Where to stay: When your one-bedroom apartment starts to feel cramped, head to this 13-acre mountain view home to spread out and lap up those gorgeous views.
Slide 6 of 7: 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. 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: This charming cottage may look twee but the amenities (Japanese cedar hot tub, outdoor fireplace, air-conditioning and high-speed Wi-Fi) are totally modern.
Slide 7 of 7: 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 a socially distanced 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: Grab your entire quarantine pod and head to this rustic lodging center that can sleep up to 12 people. And how do you feed all those people? By making use of the massive pizza oven, of course. RELATED: The 8 Most Charming Small Towns in New York

1. Cooperstown

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.

Where to stay: How does having an entire chalet to yourself sound? This camping cottage located in nearby Cherry Valley can fit up to four guests and boasts an impressive array of activities on the grounds including tennis, basketball, minigolf, non motorized boating, a beach and more. (Just make sure to double check which activities are currently available before you book.)

RELATED: 7 Artsy Day Trips Every Culture-Loving New Yorker Needs to Take

2. Narrowsburg

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 that’s now open for online orders and curbside pickup.

Where to stay: Sit back and relax at the Little House in the Flats that’s located across the street from the Delaware River and just a short walk to Narrowburg’s main street. After a day of hitting the trails, fire up the gas grill and unwind with a glass of wine on the wrap-around porch.

3. Pawling

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.

Where to stay: Sleep under the stars in the Moon Lodge Yurt that can accommodate up to three guests and is equipped with a wood-burning stove, outdoor shower and fire pit.

4. Millerton

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.

Where to stay: This two-bedroom cabin comes complete with river views and easy access to fishing and the Appalachian Trail.

5. Rosendale

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.

Where to stay: When your one-bedroom apartment starts to feel cramped, head to this 13-acre mountain view home to spread out and lap up those gorgeous views.

6. Wassaic (and Amenia)

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. 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: This charming cottage may look twee but the amenities (Japanese cedar hot tub, outdoor fireplace, air-conditioning and high-speed Wi-Fi) are totally modern.

7. Stone Ridge

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 a socially distanced 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: Grab your entire quarantine pod and head to this rustic lodging center that can sleep up to 12 people. And how do you feed all those people? By making use of the massive pizza oven, of course.

RELATED: The 8 Most Charming Small Towns in New York

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