Things To Do In Greenwich CT: Top 23 Most Unique Spots | Stanton House Inn

Things to Do in Greenwich CT: Top 23 Most Unique Spots

Spring cherry blossoms in front of the YMCA of Greenwich in downtown Greenwich, ConnecticutLooking for a getaway to escape the hurriedness of everyday life?

 
Look no further than Greenwich, Connecticut!
 
On the Long Island Sound and just a short train ride away from New York City, it’s been an irresistible vacation destination since the 1840s.
This cozy coastal town famous for its hedge funds is full of all kinds of activities to satisfy any traveler. Shopping enthusiasts have plenty of spots to explore while nature lovers will be thrilled by its beauty.
 
Plus, you’ll find unique restaurants offering delicious dishes ranging from local specialties to international cuisine!
 
So if you’re unsure what there is do in this charming spot – we’re here to help.
 
Here are some hand-picked things perfect for your trip planing whatever kind of explorer may you consider yourself being!

 

 

Below, we’ve provided a hand-picked list of the best things to do in Greenwich, CT, for every kind of traveler visiting Greenwich.

Need a visual for a quick day trip to Greenwich?

Then check out our quick video guide to visiting Greenwich, or keep scrolling for a visual guide to a day trip in Greenwich. Then, read on for descriptions of everything in the video and much more.

 

map of the top things to do in Greenwich, CT. Absolute can't miss points include: Greenwich Avenue, Greenwich Point Park, Greenwich Polo Club, and the Bruce Museum.

Map design by Stanton House Inn using resources from Flaticon.com

Table of Contents

  1. Things to Do This Weekend in Greenwich, CT
    1. Putnam Cottage
    2. Shopping, Spas, and Restaurants in Downtown Greenwich
    3. Greenwich Art Galleries
    4. The Bush-Holley House & Greenwich Historical Society
    5. The Bruce Museum
    6. Greenwich Point Park
    7. The Greenwich Audubon Center
    8. Great Captain’s Island & Little Captain’s Island
    9. Montgomery Pinetum & Pomerance Park
    10. Mianus River State Park
  2. More Things to Do in Greenwich, Connecticut
    1. Babcock Preserve
    2. Greenwich Mansions
    3. Greenwich Polo Club
    4. Old Greenwich
    5. Greenwich, CT, Real Estate
  3. What to do near Greenwich, CT
    1. Things to do in Stamford, CT
    2. Things to do in Norwalk, CT
    3. Things to do in New Haven, CT
    4. Things to do in Westchester County, NY
    5. Things to do in Mystic, CT
  4. Directions & Airports
  5. The Best Times to Visit Greenwich
    1. Greenwich Events
  6. Best Places to Stay in Greenwich, and Greenwich, CT Hotels

 

The 15 Best Things to Do in Greenwich, CT

Greenwich is a destination in its own right. Right on the coast of Long Island Sound, there are a wide variety of things to do in both Greenwich. And the trip from NYC to Greenwich is a short one, however you make it.

 

This beautiful town is the perfect location to plan a quick getaway. Greenwich is regularly rated one of the most cute towns in Connecticut, and other nearby towns are no different. Greenwich is also perfect for a longer stay to explore the hidden gems of the area.

Top 10 Things to Do in Greenwich, Connecticut, This Weekend and More

There’s a surprising amount of things to do here in town and nearby!

 

Whether a high-end shopping trip, touring Greenwich mansions is your thing, or something a little more rustic, like outdoor activities or visiting one of the four beaches, Greenwich is a perfect destination.

 

Most downtown Greenwich attractions and activities are just a short walk from our boutique inn. It’s also fun to explore other diverse neighborhoods that make-up Greenwich.

 

We can easily argue that Greenwich is one of the most unique attractions in all of southern Connecticut!

 

Though we may be a bit biased.

 

 

 Free Map of Greenwich: If you’re more the visual type, you can also download a free copy of the Greenwich, CT, Map. It has all the local attractions, activities, and things to do in Greenwich.

 

Some of our favorite things to do in Greenwich for a day or the weekend include:Top 8 attractions and activities in Greenwich, Connecticut; perfect for a day trip or a long weekend here. Don't miss: Greenwich Avenue, Greenwich Point Park, the Bruce Museum, and the Greenwich Polo Club
Infographic design by Stanton House Inn

 

Putnam Cottage, one of the best things to do in Greenwich, CT1) Putnam Cottage

Known as Knapp’s Tavern during the American Revolution, Putnam Cottage is supposedly where Revolutionary War General Israel Putnam started his ride to escape the British.

He fled Putnam Cottage and rode his horse straight over a cliff. The act earned his position on the town seal for Greenwich in one fell-swoop, as the British refused to be so daring.

 

While Putnam is quite famous here, the most famous visitor was George Washington. He stopped in and fed his troops here during the Revolutionary War. And unlike some places that make similar claims that George Washington slept there, there’s documentation to prove it!

Putnam Cottage is situated in the Putnam Hill Historic District of town, right on the Boston Post Road, AKA East Putnam Avenue. And the Putnam Hill chapter of the Daughters of the American Revolution offers tours of the house, the carriage barn, and vegetable garden out back.

Aside from Putnam Cottage, some other historic buildings to be on the lookout for in Putnam Hill include the churches: Second Congregational Church and Christ Church Greenwich.

There’s a plaque at Second Congregational Church highlighting the point where George Washington stopped to remark on the view. Back then, there was a clear view to Long Island Sound, with nothing but farms in-between the high point and the shoreline.

 

2) Greenwich Avenue & Downtown Greenwich

The top of Greenwich Avenue, looking towards First Presbyterian ChurchThere are more than enough stores to keep even the biggest shopper busy on “the Ave,” as locals call Greenwich Avenue.

Shopping

For more than a few people, one of their favorite things to do in Greenwich is shopping.

Saks Fifth Avenue, Hermes, and Lululemon are a few of the many stores you’ll find on Greenwich Avenue.

While there are plenty of very high-end opportunities in the downtown Greenwich shopping district, there are also still some local stores as well.

There’s no question that Greenwich Avenue is one of the best Greenwich CT tourist attractions in and of itself.

And once you’ve exhausted yourself from shopping for the day, there’s plenty more to do here.

Some of the historic buildings to see here include:

  • Storefronts themselves
  • The Beaux Arts Greenwich Senior Center, formerly the town hall
  • First Presbyterian Church, at the top of Greenwich Avenue

Enjoying a spa day at one of the spas along Greenwich Avenue is a great way to relax. Some of the local spas are some of the best spas in New England.

Or relax with a cup of coffee at one of the parks near to Greenwich Avenue:

  • Greenwich Town Common, centered between the Old Town Hall (now the Civic Center) and the modern Town Hall (the former high school)
  • Bruce Park, close to The Bruce Museum

Both spots feature picnic tables.

Dining

And enjoying dinner at one of the various Greenwich, CT, restaurants in our downtown is one of the most romantic things to do in Connecticut!

 

 

The shopping and dining scene alone draw people to Greenwich! A few more of our guides for dining along Greenwich Avenue down to Greenwich Harbor include:

Are you visiting Greenwich CT this weekend and looking for what to do? Read all about the events and activities in Greenwich this weekend to start planning today!

3) Art Galleries

Ever since the Cos Cob Art Colony at the Bush-Holley House, Greenwich has attracted artists of all kinds.

Each year in May, visitors flock to Greenwich, Connecticut, to view the works of over 120 artists at the annual Art-to-the-Avenue festival. During this unique event, Greenwich Avenue turns into a strolling gallery complete with musicians, street performers, and beautiful works of art for sale. This Connecticut spring festival is not one to miss!

And while Art to the Avenue is a spring event, there are plenty of Greenwich art galleries open year-round waiting to be explored!

Start at a free art gallery, the Flinn Gallery at the Greenwich Library on West Putnam Avenue, stroll along Greenwich Avenue, then finish the afternoon at the Bruce Museum.

The various art galleries and artist exhibition spaces made our list of the most romantic things to do in Greenwich, by the way.

Bush-Holley House and Greenwich Historical Society4) Bush-Holley House & Greenwich Historical Society

Sited on lovely Strickland Road, the historic Bush-Holley House has served as:

  • A farm
  • A hotel
  • A boarding house
  • The site of the Cos Cob art colony, the first in Connecticut and former center of American Impressionist art

John Henry Twachtman founded the Cos Cob art colony around 1889. Later, many other prominent Impressionists joined him, including Theodore Robinson, J. Alden Weir, and Childe Hassam.

Today, the Bush-Holley House is the home of the Greenwich Historical Society.  This National Historic Landmark offers tours of the house and the town’s colonial and artistic past with two exhibits:

  • One on the period of the New Nation (the Revolutionary War Era, 1790-1825)
  • And another about the Cos Cob Art Colony (1890-1925)

The Greenwich Historical Society will teach you such facts as why locals named Greenwich, Connecticut, in honor of Greenwich, in London.

Greenwich was Queen Elizabeth’s favorite town, so locals hoped sharing the same name would gain her favor, by the way.

The historic buildings and gardens at the Bush-Holley House are well-worth a visit to learn the fascinating history of Greenwich!

5) Bruce Museum

Near the Greenwich harbor, the Bruce Museum offers both science and art exhibits. Its wide array of holdings include items related to anthropology, natural history, decorative art, and fine art. A visit to the Bruce Museum is wonderful throughout the year with its rotating exhibits, as well as festivals and education programs.

And their gift shop is a great choice for unique presents and Connecticut souvenirs.

Most locals have fond memories of visiting the Bruce Museum as kids. But this Greenwich, CT, museum has more than enough appeal for adults, too.

The Bruce Museum also hosts 2 great events. The Outdoor Arts Festival happens in the fall, while the Outdoor Crafts Festival is in the spring.

Be sure to checkout this top pick of Connecticut museums the next time you’re here. And getting a little fresh air afterwards at nearby Bruce Park is never a bad idea.

 

Autumn at Greenwich Point Park, a walk there is one of the best things to do in Greenwich, CT6) Greenwich Point Park

What started as a waterfront estate of wealthy New Yorker J. Kennedy Tod named Innis Arden is now a favorite Greenwich park.

Greenwich Point Park is now the most visited of the fantastic beaches near Greenwich, CT. Little hidden extras like a view of the Manhattan skyline on the horizon add to the miles of walking trails.

A long sandy beach makes it by far the best of all the Greenwich beaches along Long Island Sound.

But Greenwich Point Park also has plenty of opportunities for boating and water activities.

And the views of the Manhattan skyline are a wonderful sight. Plus, the Bruce Musem Seaside Center here is another opportunity to explore local natural history exhibits.

 

7) Greenwich Audubon Center

The Greenwich Audubon Center opened in 1942. It was the National Audubon Society’s first environmental education center. The Greenwich Audubon Center is made up of 285 acres of land and is home to a large number of native plant and animal species. There are miles of walking trails to explore as well as conservation events and nature education programs at the Kimberlin Nature Education Center. The Hilfiger Children’s Learning Center within the nature center especially is a major draw for families.

When you visit Greenwich Audubon Center, you’ll always find something exciting to do!

8) Great Captain Island & Island Beach

Locals call Little Captain’s Island in Greenwich Harbor simply Island Beach. The ferry from Arch Street to the island is relaxing, and sitting on the beach looking back towards the Greenwich coast is a gorgeous view.

Time has preserved Great Captain Island, the largest of the chain of three islands off the coast of Greenwich, in its natural state. Great Captain Island is an ideal opportunity to see the diverse bird species in our area, as well as one of the most beautiful and historic Connecticut lighthouses on the island. The town offers ferry service to both Great Captain Island and Island Beach in the summer months from the Arch Street ferry dock.

The ride through Greenwich Harbor, past the mansions of Belle Haven, is delightful. And the harbor walk from Arch Street down Steamboat Road is a pleasant way to pass some time while you wait for your ferry time.

9) Montgomery Pinetum & Pomerance Park

These two parks interlock and are nestled a short distance from the Post Road in Cos Cob. Both parks, former estates, feature interesting history between them.

Montgomery Pinetum Park

 

Park bench overlooking at pond at Montgomery Pinetum in Cos CobMontgomery Pinetum, as the name implies, is most famous for the rare conifers scattered throughout the site. Colonel Robert Montgomery, a successful businessman and horticulturist, planted the trees on his estate. His most famous contributions to society were:

  • A donation of 200 specimen trees to the New York Botanical Garden in 1947
  • The Fairchild Tropical Garden in Coral Gables, Florida
  • The Pinetum named in his honor here in Greenwich

The grounds of Montgomery Pinetum Park are lovely, and connect to 102 acres of forest full of trails to explore.

This is also the home of the Greenwich Botanical Center, with the Greenwich town greenhouse and garden education center.

Pomerance Park

Walk through the hiking trails to reach Pomerance Park. A more recent acquisition for the town of Greenwich, this public park includes a beautiful pond in the middle of more rugged woods.

This park was the seminal site of the Boy Scouts of America. To stop local boys from drawing lewd images and obscenities on his gate, Ernest Thompson Seton started a group the “League of Woodcraft Indians” that eventually grew into the more famous organization.

Two-time Pulitzer prize historic writer Barbara Tuchman later occupied the property, where she wrote, The Guns of August, a critique of the events leading up to the First World War. This book heavily influenced President John F. Kennedy when he and his staff were handling the Cuban Missile Crisis.

The town tore-down the historic buildings on the site to avoid dealing with partying teenagers, but the stone foundation and walls still stand.

10) Mianus River State Park

The Mianus River in Mianus River State Park, from the Greenwich, Connecticut, sideNamed after the 20-mile river that flows through it, Mianus River State Park is situated between Stamford and Greenwich, Connecticut. The park features over 400 acres of forests, wetlands, rock formations, and gardens that are just waiting to be explored.

This historic State Park is a beloved destination for outdoor enthusiasts and attracts everyone from joggers and hikers to mountain bikers and fishermen. It’s one of the best state parks in Connecticut, let alone Greenwich and Stamford.

Even More Things to Do in Greenwich, CT

Finished-up the top 10 list? There’s plenty more things to do in Greenwich. After all, it’s the largest town in Connecticut by geographic size, so of course there’d be more to explore.

Back Greenwich

Most of Greenwich’s landmass stretches north from the Boston Post Road towards the town of Bedford, New York.

This much less densely populated portion of town features old farmsteads, palatial estate mansions, and tranquil woods and streams. Plus, the aforementioned Greenwich Audubon Center in North Greenwich.

It’s the perfect space to enjoy the best Connecticut outdoor activities!

Hiking trails in Babcock Preserve

For an afternoon hike, the Babcock Preserve in Greenwich, CT, offers 300 sprawling acres of woodlands, an extensive network of trails, and a wide variety of plants and animals. The Babcock Preserve is the largest town park in the area and is an ideal destination for nature lovers and outdoor enthusiasts. This public park is in the area north of the Merritt Parkway, so the next time you’re passing by, grab your hiking boots, pick up a Babcock Preserve trail map, and raise your heartrate!

Driving or Biking by Greenwich Mansions

historic mansion in the Cos Cob neighborhood of GreenwichMore than a few guests newly arrived in Greenwich will remark on how many schools and institutions there are in Back Greenwich.

The reality is that so many of the mansions in Greenwich are so large that they just look like institutions.

Taking a trip around Back Greenwich to see some of the largest estates can be a pleasant afternoon in and of itself.

 

Watching a Greenwich Polo Club Game

Polo playersIf dressing up, reveling in the sunshine, and watching a grand old-fashioned game of polo sounds like a day well-spent, you’re in luck!

The Greenwich Polo Club is recognized as one of the most elite in the world. Watching one of the White Birch Polo Team matches is a summer tradition in Greenwich.

The Greenwich Polo Club experience is akin to the Kentucky Derby, except the match lasts much longer than a horse race.

Free things to do in Greenwich

While Greenwich is known for wealth and success, not everything requires your wallet.

In fact, some of the best free things to do in Connecticut are right here in Greenwich, such as:

Top things to do in Greenwich with kids

Many of our guests come to town to spend quality time with kids. So a list of family-friendly activities in Greenwich seems necessary.

Some of the best things to do with kids in Greenwich, Connecticut, include:

  • The Bruce Museum and Greenwich Historical Society
  • Exploring the parks, like Binney Park, Greenwich Point Park, Bruce Park, Byram Shore Park, and Cos Cob Park, with lunch at picnic tables or just to play
  • The Hilfiger Children’s Learning Center at Kimberlin Nature Education Center in the Greenwich Audubon Center is worth a visit
  • The hiking and walking trails throughout town

Things to do in Greenwich at night

Many of our guest recommendations for date night ideas and the best things to do at night in Greenwich center around the restaurants and bars of Greenwich Avenue and West Putnam Avenue.

Downtown Greenwich and nearby lends itself to several different varieties of nights on the town, including:

There are even still dive bars in the area, if you’d rather keep your favorite flannel on!

Things to do in Old Greenwich

When it comes to attractions, Old Greenwich is more than Greenwich Point Park. Greenwich’s own beachtown offers such quaint and downright cute points of interest as its own downtown shopping area and Binney Park.

It also features even more fantastic dining options. Some Old Greenwich favorites include Lugano, Le Fat Poodle, and Applausi.

Greenwich Real Estate

Let’s face it, there’s a reason that realtors setup shop on the main street of most tourist destinations.

Even if you have no plans to actually purchase a home, checking out Greenwich, CT, real estate market for sale can be a fun way to pass some time or fantasize.

Besides, open houses are a great way to see the inside of some gorgeous houses in the area. And they’ve usually got some decent food.

That said, the various hedge funds and investment bankers in town and in New York City have pushed home prices and real estate in general quite high, so be ready for some sticker shock.

How to get married in Greenwich

Are you planning a wedding in town?

Congratulations and best wishes!

In case you need some ideas, be sure to read our guide to wedding venues in Greenwich. It’s got wedding venues both in town and in the surrounding towns.

What to Do Near Greenwich, Connecticut

One of the best parts about being in Greenwich is its proximity to so many other attractions and activities in nearby towns. All Westchester County, NY, Fairfield County, and the Connecticut shoreline are easily accessible from Greenwich.

It definitely broadens the possibilities for CT day trips!

Be sure to download the Connecticut Travel Guide for our tips on the best attractions, activities, and things to do across Connecticut.

Top Things to Do in Stamford, CT

glass ceiling at the usb building in stamford, one of the best things to do in greenwich and stamford, ctJust to the east of Greenwich on Long Island Sound sits the city of Stamford, Connecticut. The third-largest city in Connecticut makes a modern city’s amenities easily accessible to visitors and locals in Greenwich.

Without the trek into New York City, anyway.

Check-out our list of the top things to do in Stamford, Connecticut, or check-out some of our most popular guides on Stamford:

The drive from Greenwich CT to Stamford CT is only about 10 minutes.

Things to do in Norwalk, Connecticut

A little further up the Long Island Sound shoreline from Greenwich and Stamford is the unpretentious and diverse city of Norwalk.

A former industrial town, Norwalk is now known for its diverse food scene, Victorian history, and the Maritime Aquarium.

Be sure to check-out our guide to the activities, attractions, and things to do in Norwalk, CT, before you visit!

Things to do in Fairfield, CT

The charming beach town of Fairfield, Connecticut, hosts an expansive territory to explore.

The list of attractions in Fairfield includes history, the arts, and hiking. Plus, plenty of beaches.

Best things to do in Bridgeport, Connecticut

Yes, I spent the time writing a guide to Bridgeport!

If it’s one thing locals seem to be united on, it’s making fun of the largest city in Connecticut, and the fifth largest in New England.

But there’s actually a surprising number of things to do in Bridgeport, Connecticut. Holdover from its wealthy heydays include:

More recent additions, thanks to low rents and ample space for the Gold Coast include:

Top Attractions in New Haven, Connecticut

architecture yale campus things to do in new haven ct Things to Do in Greenwich CT: Top 23 Most Unique SpotsAbout an hour drive from Greenwich, there’s more to do in New Haven than just visiting IKEA or Yale University.

That said, Yale University does host a number of major New Haven attractions. And sometimes, you just have to have some Swedish meatballs.

But the birthplace of hamburgers and apizza-style pizza in America has a thriving culinary scene.

And some major historical moments of America’s Industrial Revolution happened here. Plus, a few of the most impressive art and scientific collections in the Western Hemisphere.

Be sure to read through our guide to the best activities, attractions, and things to do in New Haven, CT.

Things to Do in the Hudson Valley of NY

The Hudson River Valley is closer to Greenwich than much of Connecticut. And there are plenty of things to do in the Hudson Valley while exploring the stretch from Beacon, NY, down to Yonkers, New York.

From Halloween festivities in Sleepy Hollow, NY, to summer hiking throughout the region, there’s plenty to do here.

Some of ourfavorite things to do in Westchester County and the Hudson Valley include parks, attractions, and cute, quaint towns.

Best Things to Do in Mystic, Connecticut

BF Clyde's Cider MillMystic is about an hour and a half from Greenwich, almost to the Rhode Island border.

But we get asked about this destination a lot, especially guests on driving tours up the Long Island Sound coast, stopping with us before visiting Mystic.

And luckily, everyone in Connecticut has been to Mystic and Stonington, CT, on multiple occasions.

Check out our list of the best activities, attractions, and things to do in Mystic, Connecticut, before your next trip.

Greenwich, CT, Directions & Airports

Ready to plan a trip to Greenwich, one of the easiest train trips from NYC?

Be sure to read our guide for directions to downtown Greenwich. It has driving directions to various points in Greenwich. It also features a guide to taking Metro North line from Grand Central Terminal in NYC to the Greenwich train station at the bottom of Greenwich Avenue.

We also have a guide to the airports closest to Greenwich, Connecticut.

Best Times to Visit Town

Spring, summer and fall are the busiest times of the year to visit Greenwich, and for good reason. The weather is perfect for a visit to Greenwich, as our hottest days are still quite pleasant compared to the rest of the country.

And even thunderstorms pass quickly. As they say about New England weather, if you don’t like it, wait 10 minutes.

Springtime in Connecticut

And spring in Connecticut features bursts of flowers to celebrate the longer, warmer days after the cold nights of winter.

Don’t miss our guides to individual months:

Connecticut in the Summer

Summer in Connecticut is absolutely glorious. Perfect weather lends itself to long days of hiking, CT beaches, or any other activity you can think of.

Be sure to read our guides to the month you’re thinking about visiting CT in the summer:

Fall

There’s a reason why Fall in Connecticut is so well-known. It’s worth a trip here in September, October, or even November.

Winter

Second Congregational Church in winter, just around the corner from Stanton House Inn in downtown GreenwichBut winter in Connecticut has its own peaceful tranquility.

Greenwich and Connecticut in general still offers a New England getaway without the drive, or the need to figure-out how to ski.

And no matter where in the state you are, there are plenty of winter activities to keep you entertained.

We’ve got guides for these months, as well:

Be sure to read our guide to attractions, activities, and things to do in Greenwich in winter to start daydreaming!

Top Greenwich Events

With a multitude of events taking place throughout the year, it can be difficult to choose which ones to attend.

That’s why we’ve compiled a list of some of our favorites!

See the full list and our calendar of Greenwich events, but top picks include:

  • Focus on French Cinema
  • Bruce Museum’s Outdoor Spring Crafts Festival
  • Greenwich International Film Festival
  • Greenwich Wine and Food
  • The annual Art to the Avenue event on Greenwich Avenue
  • Outdoor Fall Arts Festival at the Bruce Museum
  • Greenwich Holiday Stroll and Fair

Some of our favorite annual events in the rest of Fairfield County (and nearby) include:

  • Oktoberfest at Bear Mountain

What About Hotels? Where’s the Best Place to Stay in Greenwich, CT?

That’s easy!

 

The living room, dining room, and hallway of Stanton House InnStanton House Inn is a downtown Greenwich, CT, bed and breakfast inn. A former boarding house, our inn now offers all sorts of cozy Greenwich accommodations. From romantic suites (some with whirlpool tubs in the room) to spacious historic guest rooms, we have you covered.

Our serene bed and breakfast inn is close to everything downtown. The Inn’s common areas are an opportunity to explore the inside of a beautiful historic Greenwich mansion. The outdoor swimming pool, patio, and gardens surrounding our bed and breakfast are also a popular attraction in the warm months.

Be sure to explore our list of CT vacation packages to plan a romantic weekend getaway in Greenwich, Connecticut. Our bed and breakfast spa services add a little something special to your stay.

If a Greenwich, CT, bed and breakfast inn isn’t for you, be sure to explore our guide to Greenwich, CT, hotels to find one that’s perfect for you. Options for hotels within Greenwich’s town borders, all of which are dog-friendly getaways, are:

And there are plenty more chain hotels to browse among the list of hotels in Stamford, CT, right next door.

We hope to see you soon!


Updated and republished August 11, 2023