Towns In Westchester County: Top 8 Most Unique Spots | Stanton House Inn
Croton dam in one of the cutest towns in Westchester County

8 Towns in Westchester County That You’ll Love to Visit

Towns in Westchester County While Greenwich is a fantastic destination to visit all on its own, a trip to this New England paradise would nearly be wasted without visiting the nearby towns. Just beyond Greenwich, you’ll find beautiful and historic Westchester County. Also used as a getaway from the hustle and bustle of New York City, the towns in Westchester County make ideal day trips for our guests at Stanton House Inn! If you’re looking for places to fill your vacation itinerary, these local treasures are not to be overlooked!


There are so many incredible places to see near Greenwich, you’ll hardly know where to start! Find more towns in Westchester County and beyond by downloading our free Greenwich, CT Vacation Guide!

8 of the Best Towns in Westchester County to Visit

Just a short drive from Greenwich, you’ll find a wide variety of fascinating towns to explore in Westchester County. Here are just a few of the most popular among our guests that we’re sure you’ll love as well!


White Plains

Also known as the commercial hub of Westchester, White Plains, NY is an affluent suburban community. Many visitors travel to this town to take advantage of the fantastic restaurants and shopping opportunities. In fact, the downtown area of White Plains offers a variety of shopping districts and malls filled with well-known New York-based stores. From high-end brands to affordable souvenirs and merchandise, you’ll find it all!



Formerly known as the village of Rye, New York, this charming waterside town received its official charter as a city in 1942. Since then, it has seen a variety of visitors who are eager to discover the rich history of the area. Rye sits on the National Register of Historic Places and is also home to an Art-Deco style amusement park and the popular Rye Playland. You’re sure to love the abundance of things to do including ice skating, thrilling rides, lounging on the beach, and much more!

Sleepy Hollow

Yes, this town does not just exist in the folk legend. It is a very quaint village located about 30 miles north of New York City. Here, you’ll find the Rockefeller State Park Preserve, a lovely wooded hiking trail with many examples of varied habitats. If you wander into the famous cemetery of Sleepy Hollow, you’ll find the graves of influential figures in American history including Washington Irving and Andrew Carnegie. Do you find it a coincidence that this tiny town is known as one of the most haunted places in America considering it is presumably the setting for one of America’s most chilling legends.



Just south of Sleepy Hollow, Tarrytown is not as famous as its neighboring village. But there are plenty of attractions, activities, and things to do in Tarrytown, NY, throughout the year, not just in the Halloween season. The main street feels like a Norman Rockwell painting, with a much more diverse dining scene. And the parks in the hills overlooking town and down by the Hudson River are splendid.


Waccabuc, New York is a hamlet and lake town near Lewisboro. It is commonly known by the locals as “New York’s secret suburb” and houses a collection of privacy-loving C.E.O’s and bright stars. Despite is quiet and laid-back atmosphere, there are many things to do! Visitors come to Waccabuc to see the stunning real estate and Castle Rock, a popular cliff jumping destination.


City Island

This unique little island hamlet isn’t part of Westchester County anymore. It seceded from the county and joined New York City in 1898. But it’s just off the coast of the Bronx and Westchester County. And a summertime visit to the City Island neighborhood is a shorter (and cheaper) trip for a quaint New England fishing village vibe.



Most people just pass through the Croton train station, but there’s more here to explore than just that. The most historic of the things to do in Croton-on-Hudson, NY, is visiting Cortlandt Manor, especially in the fall for the Great Jack O’Lantern Blaze.



The original center of American filmmaking, Mamaroneck is still an artistic center. It’s still the home of Archie Comics. But its clusters of historic villages and verdant landscapes along the peaceful waterfront of Long Island Sound is a draw in an of itself. Some of the more unique spots to visit in Mamaroneck include the Skinny House, and, of course, the waterfront parks. And the village of Larchmont, NY, has a distinctly French feel, thanks to the staff at the French-American School of New York.


Pound Ridge

Up in the Northwest corner of Westchester County, the town of Pound Ridge, NY, is famous for its rolling hills and woods. Meaning: not a lot of people here. But there does appear to be a high concentration of celebrities, and the hiking trails at Ward Pound Ridge Reservation and other parks is splendid. Plus, you can score a NYC-level meal at the Inn at Pound Ridge, or work on your swing at the Pound Ridge Golf Club.


Return to Stanton House Inn for the Ultimate Greenwich, CT Experience

After exploring the various towns of Westchester County, we invite you to come back and enjoy the enchantment of Greenwich in our historic inn. From here, you’ll be able to reach the best Fairfield County destinations and the most cute towns in Connecticut, as well.


Recognized as the most romantic bed and breakfast in Connecticut, The Stanton House Inn is a destination for couples. Our beautiful guest rooms exude historic charm while the rest of the inn warmly welcomes visitors with lovely decor and tranquil ambiance. Don’t forget to take advantage of our inn’s exclusive vacation packages and extras! Book your stay at the Stanton House Inn today and we look forward to welcoming you soon!


Updated and republished: October 8, 2023

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