For many who are leaving the city and considering the NYC suburbs, one of the biggest hesitations is losing the walkability that the city offers and becoming isolated in a home away from conveniences. If you are looking for a home that is still within walking distance to the downtown amenities, schools and parks, there are a handful of walkable Westchester towns and Fairfield County locations we suggest exploring. Below are some of the most walkable towns in Westchester County, New York and Fairfield County, Connecticut.

Tarrytown

This sought after Rivertown features a charming and lively downtown that is full of mom-and-pop shops, musical and cultural events, and diverse dining options. The train is situated near the waterfront along with the Scenic Hudson RiverWalk Park, which is just another draw to this scenic and walkable Westchester town. New construction luxury townhouses and condos are sprawled along the waterfront, while the streets surrounding downtown offer single-family homes within walking distance to the downtown amenities. If you’re looking for a character-rich town with walkable features and an easy commute to the city, Tarrytown may be fit for you. It’s one of the most walkable towns in Westchester County.

Pleasantville

A small town with a large personality, Pleasantville is perfect for anyone—from singles and young families to empty nesters. The quaint shops, cultural events, and entertainment make this hip and walkable village one of the most desirable towns in Westchester, New York. With many of the town’s amenities spread across the stretch of downtown, you’ll discover new and exciting spots depending on the direction you explore. Touted as a “walk to all” town, the tree-lined streets are full of homes on compact lot sizes. Plus, Pleasantville is a desirable location within the county, convenient to major highways, surrounding cities, and town centers.

Mamaroneck

Mamaroneck, a diverse and culturally rich town on Westchester County's Sound Shore, in known for its excellent connectivity. Mamaroneck Avenue, with its pedestrian-friendly sidewalks, leads directly to the Metro-North station and parks, fostering a walkable and cohesive community. Tree-lined streets and well-maintained sidewalks make strolling through the town a pleasant experience. Mamaroneck’s waterfront parks and marinas along the Long Island Sound are easily accessible, providing beautiful views and recreational opportunities just a leisurely walk away.

Larchmont

As a quaint village with two separate downtown areas, this shoreline village offers walkability for many of life’s daily activities. From walking kids to school and their after-school activities to everyday errands and shopping trips, you’ll find homes that accommodate this lifestyle. The train is also within walking distance for a convenient commute to the city. The town’s quiet sophistication along the Sound Shore appeals to many city transplants looking to ease into suburban living. If you’re exploring what are the most walkable towns in Westchester County, NY, Larchmont is worth considering.

White Plains

As a centralized location with one of the county’s most diverse mix of housing options, White Plains is one of the best towns in Westchester County, NY for those who still long for a city vibe. From co-ops and condos in the heart of the downtown, to single family homes on tree lined streets within city limits, there is a home and lifestyle for just about anyone. Its extremely walkable downtown is home to many commercial offices, a diverse mix of restaurants, and prime shopping malls. Plus, a quick 35 minute train ride to Grand Central makes this one of the best places to live in Westchester and commute to NYC.

Pelham

Pelham boasts a small village with a quick commute to the city. As a strongly residential town, you'll find many homes on sidewalk-lined streets that are within a mile from the village downtown and train. This town is full of history and a mix of architectural styles - anything from colonials and Victorians to Tudors and ranches. You can expect a close-knit, supportive community that appreciates everything their town has to offer them and many residents will tell you that Pelham is one of the best towns in Westchester.

Katonah

Within this Northern Westchester hamlet, you’ll find a community that is full of pride for maintaining their heritage and small town appeal. Quaint yet energetic, the downtown has a variety of established and new mom and pop shops, artistic and cultural events, and plenty of green space for exploring, making it one of the best downtowns in Westchester. Being within walking distance to the village and train is a beloved lifestyle that many long to achieve. The surrounding homes are on picturesque streets and full of character and the walkability to town allows residents to stay connected to the heart of this village, making Katonah one of the many towns in Westchester, New York where walkability and charm go hand in hand. 

Stamford

If you’re looking for walking towns, look no further than Downtown Stamford. This standout walkable town in Connecticut offers a true city vibe, with restaurants, shopping and entertainment within steps from your front door. 

Due to its flourishing restaurant and bar scene, Stamford attracts many young individuals, with Harbor Point recognized as the main entertainment area and the second most walkable neighborhood in Stamford. Located directly on the Long Island Sound, Harbor Point is considered a “Live-Work-Play” community with an abundance of shopping and dining options. The Harbor Point Trolley is the most exciting way to get around town, which runs everyday and makes 14 stops throughout - and best of all, it's free. 

Cos Cob

With only about 7,000 people and with a size of only 4.5 square miles, Cos Cob is an intimate and convenient community. Cos Cob is a neighborhood of Greenwich, the closest CT town to NYC. Playgrounds, the post office and the terrific public library are often no more than a five-minute stroll away, and it is not uncommon to see people making their way there on the shoulders of roads, undeterred by the occasional lack of sidewalks. The town’s commercial hub, which houses coffee cafes, gourmet cheese shops, upscale juice bars and numerous dining options, is bordered by residential neighborhoods on both sides, allowing families to enjoy a variety of options only minutes from their doorsteps. It’s one of the best small towns in Connecticut for walkability and community charm.

New Canaan

New Canaan is a beautiful town that attracts many young families due to its highly rated public school system and one of the best downtowns in Connecticut. You can find a classic colonial home or modern masterpiece within walking distance to fine restaurants, boutiques, antique shops, a movie theater, and interior design shops. Elm Street is considered the heart of the town center and from there you can walk up and down small alleyways to find hidden gems.  Surrounding town you can find a mix of newly built luxury townhouses that could cost as much as $3 million, as well as more modest condos, ranging from $350,000. New Canaan is widely considered one of the nicest towns in Connecticut and a best town to live in CT for those seeking both style and substance.

Fairfield

Fairfield, CT's walkable downtown is a vibrant and inviting area that epitomizes the charm and convenience of suburban living with numerous shops, restaurants and cafes. Centered around the bustling Post Road, the downtown area allows residents to embrace a lifestyle where daily errands, social gatherings, and an active lifestyle seamlessly combine. Well-maintained sidewalks and pedestrian-friendly paths encourage exploration of the town's hidden gems, from charming parks and scenic overlooks to local shops and markets. Landmarks such as the Fairfield Theatre Company and the Fairfield Museum and History Center add cultural depth to the downtown experience. Additionally, seasonal farmers markets, street fairs, and outdoor concerts bring the community together, enhancing the lively atmosphere and making Fairfield one of the best towns in Connecticut.

So if you’re considering leaving the city to explore life in the NYC suburbs, one of these walking towns may be a good option for you. They provide all of the charm and serenity of suburban life without sacrificing convenience. If you’re interested in learning more about any of these towns in Westchester County, NY or Fairfield County, CT, reach out to us today. 

Take our quiz to find out which neighborhood best fits your personality or head over to our resources to learn more about the lifestyle and appeal of other wonderful towns in the NYC suburbs.