Towns Near Greenwich CT: Top 3 Most Unique | Stanton House Inn

One of the most attractive aspects of Connecticut’s Gold Coast is the region’s collection of unique and charming towns! Everyone knows that Greenwich, CT, is one of the best towns in the Northeast to visit for its:

And the trip from NYC to Greenwich is so easy!


If this historic Connecticut destination is already one of your favorites, why not take a day trip to one of the fantastic towns near Greenwich, CT, next time you visit?


That way, you can still stay at one of your favorite hotels in Greenwich, CT, while discovering even more about the area.


Here are just a few of the best New England towns perfect for a day of exploring. You can find many more on our list of cute towns in Connecticut.


Enjoying the splendor of Greenwich and devoting a day to exploration is the best way to see New England. Before honing in on what might become one of your new favorite towns near Greenwich, CT, you’ll want to make sure your visit to Greenwich is filled with unforgettable experiences.


Check-out our visitor’s guide to Greenwich, CT, for our full list of attractions, activities, and things to do in the area.

Here Are the 3 Best Towns Near Greenwich, CT

Stamford, CT

Geographically speaking, the city of Stamford, CT, is Greenwich’s next-door neighbor. This little city is one of the most “up-and-coming” cities outside of  New York City, so it’s worth a few hours of your time! We highly recommend visiting what the locals call “Little Manhattan” for its excellent restaurants, especially along Bedford Street in Downtown Stamford. There are also many exciting attractions, activities, and things to do in Stamford. Some visitor favorites include the Stamford Museum and Nature Center, Palace Theatre, and Avon Theatre.


towns near Greenwich, CT

New Canaan, CT

If you’re a fan of classic New England architecture with plenty of Old World charm, the town of New Canaan, CT, is a great place to spend an afternoon. Here, you’ll see beautiful churches, a walkable downtown district, and a 19th-century train station. In addition to the scenic sights, there are plenty of draws for art enthusiasts! To begin your tour of artistic New Canaan, take a stroll down to the Philip Johnson Glass House, the studio where the prominent artist himself once worked. New Canaan is also a favorite spot for CT fall fairs and festivals like the Harvest Fest.


Bedford, NY

Another one of the picturesque towns near Greenwich CT is right over the border in Westchester County, New York. The town of Bedford, New York, includes three small cities: Bedford Village, Bedford Hills, and Katonah. All three are lovely places to spend an easygoing afternoon! Bedford Village features a classic village green in a downtown district that’s listed on the National Registry of Historic Places. Bedford Village is also near the Mianus River Gorge Preserve, one of the best hiking trails near Greenwich and only old-growth forest left in the area.


The village of Katonah, NY is a charming little town that boasts its own train station. Wander for a bit here on one of the most charming train trips from NYC. Be sure to stop into the Katonah Museum of Art, a famous art museum and classical music venue.


Tarrytown, New York

Not quite as close as the other towns on this list, but Tarrytown, New York, is a personal favorite of mine. On the opposite side of Westchester County from Greenwich, the village of Tarrytown, NY, is a great spot to take a walk along the Hudson River, or explore the forested hills above it. Rockefeller State Park Preserve is a personal favorite.


Afterwards, head to Tarrytown’s Main Street for restaurants featuring cuisine from all over the world.


Stay Near All of the Best Towns Near Greenwich, CT!

No place does classic New England better than Greenwich, CT. That doesn’t mean you can’t branch out and explore the other Fairfield County destinations, though! Greenwich serves as an ideal jumping-off point for all of the area’s best destinations.


Be sure to read our guide to even more day trips in Connecticut, including the best beaches in all CT.


That’s why there’s no better place to rest your head than Stanton House Inn! This historic bed and breakfast features vibrant and airy suites, plus plenty of premium guest services that will make you feel right at home. Select rooms feature elegantly charming details like fireplaces, clawfoot tubs, and views of the inn’s immaculate garden!


If you’re ready for a tour of the best towns near Greenwich, CT, book a stay at Stanton House Inn today! We’ll be happy to provide even more recommendations from our local perspective so you can make the most of your stay. Happy exploring!

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