The town of Westchester sits in an odd in-between location where New York City ends and the journey to Upstate New York begins, which gives it a few unique qualities. Not only is it close enough to the city to be considered a staycation, but it also feels like a place that's so far removed from New York City that it couldn't possibly be less than 20 miles from Manhattan. Additionally, it's so close to the gateway to northern New York that it has an air of quaint small towns and historic features, without actually being that small.


In short, Westchester is a charming county that's full of adventure for those seeking it, and also full of cozy comfort for anyone looking to escape the city life without venturing too far. It should go without saying, but Westchester County definitely makes for an idyllic weekend getaway - here's why.

Related: Boston Vs. New York City: Which One Is Better For A Weekend Getaway?

Once A Royal Home, Now One Of New York's Most Famed Counties

During the 19th century, Westchester County was home to a powerful New York family who took to its land to build a castle that would soon become symbolic of the county as a whole. This initial first step drove Westchester forward as a premier destination that boasts luxury and the finest accommodations, paired with nature and landscape that rural New York is known for - except for the fact that Westchester County isn't entirely without its city-like vibe.

Since then, it's become a popular, and convenient vacation destination for anyone in the surrounding states such as Connecticut, Massachusetts, Rhode Island, and even northern New Englanders who don't mind a drive.

Extravagant Shopping In White Plains

The Westchester

White Plains sits just outside of New York City so it makes sense that it would carry with it some of the city's most notable attributes, including its shopping. Visitors will find the best outlets at The Westchester, which is home to some of the most noteworthy names in the fashion industry. Most than 150 stores line its sidewalks and it's easy enough to spend an entire weekend here along, with so much to see, window shop, and actually shop for.

Ridge Hill

Ridge Hill is another popular destination that can be found in Yonkers, and this is a great option during the spring, summer, or fall. With so many outdoor shops and plenty of dining options, it's the perfect way to soak up the temperate weather that downstate New York boasts before and after the winter season.

Cross Country Shopping Center

The Cross Country Shopping Center might not boast the same outdoor charm or an extensive number of shops that the others do, but it does feature all the most popular shops one would typically find in the mall. This shopping center is also located in Yonkers and features a small green courtyard, as well as close proximity to chic dining establishments.

Westchester County Is A Hub For Culture And The Arts

For those looking to indulge in a little bit of art and culture while they're touring the county, arts, and culture are in no short supply. With a number of theaters and museums from which to take in either of the two, once again, a weekend could easily be spent exploring them all - and you still probably wouldn't have the chance to visit everything!

Visual Arts & Museums

  • Neuberger Museum of Art in Purchase
  • Hudson Valley MOCA in Peekskill
  • Katonah Museum of Art in Katonah
  • ArtsWestchester in White Plains

Theaters & Concert Halls

  • Capitol Theater in Port Chester
  • Paramount Hudson Valley Theater in Peekskill
  • Caramoor Center for Music and the Arts in Katonah
  • Emelin Theater in Mamaroneck

The Great Outdoors, Westchester-Style

The great thing about visiting Westchester County from any of the surrounding areas is that the entirety of it gives way to beautiful nature and scenic river and hillside views, without having to travel very far. Much of this can be seen via hikes that run through the area or by driving, and the waterways make easy work of navigating the Hudson Valley's most gorgeous scenery.

Westchester Hikes

  • Bronx River Pathway
  • North-South County Trailway
  • Colonial Greenway
  • Briarcliff-Peekskill Trailway
  • Old Croton Aqueduct State Historic Trail
  • Cranberry Lake Preserve
  • Blue Mountain Reservation

Waterways And Beaches

  • George's Island
  • Croton Point
  • Cross River Reservoir
  • Playland's Beach
  • Glen Island Park (Beach)

New York's (Somewhat) Hidden Gem

Westchester County is a great destination for anyone who doesn't mind a (short) drive from the surrounding area. There are plenty of adventures to be had, along with a plethora of dining establishments, breweries, outdoor activities, and a long list of entertainment options to choose from - so you can be sure a vacation spent here, is a vacation spent well.

Next: These New York City Museums Are Always Ready To Take Visitors On A Visual Adventure