glass ceiling at the usb building in stamford, one of the best things to do in greenwich and stamford, ct

Just a short train ride away from New York City is Greenwich, CT.

 

Located on the Long Island Sound, this charming coastal town offers a variety of interesting things to do. It’s a perfect place to escape the hustle and bustle of everyday life! Whether you and yours love shopping, exploring the wonders of nature, or trying new restaurants, there’s something for you to enjoy here!

 

Not convinced on planning a visit to Greenwich, CT?

 

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

 

Local insight is so important to planning an unforgettable vacation. Let us take care of the tedious researching for you!

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
    1. Babcock Preserve
    2. Greenwich Mansions
    3. Greenwich Polo Club
    4. Old Greenwich
  3. What to do near Greenwich, CT
    1. Things to Do in Stamford, CT
    2. Things to Do in Westchester County, NY
  4. The Best Times to Visit Greenwich
    1. Greenwich Events
  5. Best Places to Stay in Greenwich, CT

The 14 Best Things to Do in Greenwich, CT

Greenwich is a destination in its own right. Located on the coast of Long Island Sound, there are a wide variety of things to do in both Greenwich.

This beautiful town, and other nearby towns, are all the perfect location to plan a quick getaway. They’re 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 and touring Greenwich mansions is your thing, or something a little more rustic, Greenwich is a perfect destination.

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

While this video is a little old, it’s full of some of the major sites in town. It’s so helpful, we’re willing to overlook the fact that it doesn’t mention us!

 

 

Read on for descriptions of everything in the video and more.

 

 

 

Free Map of Greenwich, CT: 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:

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

Known as Knapp Tavern during the American Revolution, this is supposedly where Revolutionary War General Israel Putnam started his ride to escape the British. He rode his horse straight over a cliff and earned his position on the town seal for Greenwich in one fell-swoop, as the British refused to be so daring. Putnam Cottage is situated in the Putnam Hill Historic District of town, right on the Post Road, and offers tours.

2) Enjoy Fantastic Shopping, Spas, and Restaurants in Downtown Greenwich

There are more than enough stores to keep even the biggest shopper busy on “the Ave,” as locals call it. For more than a few people, one of their favorite things to do in Greenwich is shopping. While there are plenty of very high-end opportunities in the downtown Greenwich shopping district, there are also still some local Greenwich Avenue 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.

 

Enjoying a spa day at one of the spas in Greenwich, CT, is a great way to relax. And enjoying dinner at one of the various downtown Greenwich, CT, restaurants is one of the most romantic things to do in Connecticut!

 

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 downtown Greenwich.

 

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

3) Greenwich Art Galleries

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.

And while Art to the Avenue is a spring event, there are plenty of Greenwich art galleries open year-round. The many art galleries that line the streets of downtown Greenwich are just waiting to be explored!

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

This is the site of the first art colony in Connecticut and former center of American Impressionist art. Today, the Bush-Holley House is the home of the Greenwich Historical Society.  This building offers tours of the house with two exhibits: one on the era of the New Nation (1790-1825) and another about the Cos Cob Art Colony (1890-1925). The historic buildings and gardens on the site are well-worth a visit!

5) The Bruce Museum

Located in downtown Greenwich 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.

Most locals have fond memories of visiting the Bruce Museum as kids. But it 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 museums in Greenwich, CT, the next time you’re here.

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 water-front estate of wealthy New Yorker J. Kennedy Tod named Innis Arden is now a favorite park. Greenwich Point Park is now the most visited of the fantastic beaches near Greenwich, CT, with miles of walking trails. A long sandy beach makes it by far the best of all the Greenwich beaches. But the park also has plenty of opportunities for boating and water activities, and even gorgeous views of the New York City skyline!

7) The Greenwich Audubon Center

The Greenwich Audubon Center opened in 1942. It was the National Audubon Society’s first environmental education center. The 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 trails to explore as well as conservation events and nature education programs. When you visit Greenwich Audubon Center, you’ll always find something exciting to do!

8) Great Captain’s Island & Little Captain’s Island

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

Time has preserved Great Captain’s Island, the largest of the chain of three islands off the coast of Greenwich, in its natural state. It is an ideal opportunity to see the diverse bird species in our area, as well as the beautiful lighthouse on the island. The town offers ferry service to both islands in the summer months.

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

Montgomery 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 are lovely, and connect to 102 acres of forest full of trails to explore.

Pomerance Park

Walk through the trails to reach Pomerance Park. A more recent acquisition for the town of Greenwich, Pomerance 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 mansion to avoid dealing with partying teenagers, but the stone foundation and walls still stand.

10) Mianus River State Park

Named after the 20-mile river that flows through it, Mianus River State Park is situated between Stamford and Greenwich, Connecticut, and 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 parks in Greenwich, or Stamford for that matter.

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 Bedford, New York.

 

This much less densely populated portion of town features old farmsteads, palatial estate mansions, and tranquil woods and streams.

Hiking 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. This preserve is the largest town park in the area and is an ideal destination for nature lovers and outdoor enthusiasts. This park is close to 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

More 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

If 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 their matches is a summer tradition in Greenwich. The experience is akin to the Kentucky Derby, except the match lasts much longer than a horse race.

Things to do in Old Greenwich, CT

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.

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!

Top Things to Do in Stamford, CT

Just to the east of Greenwich 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 long trek into New York City, anyway.

Check-out our list of the top things to do in Stamford, Connecticut.

Things to Do in Westchester County, NY

Westchester is closer to Greenwich than most of Connecticut. And there are plenty of things to explore in the county stretching from Peekskill down to Yonkers, New York.

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

The Best Times to Visit Greenwich, CT

Spring, summer and fall are the busiest times of the year to visit Greenwich, and for good reason. The weather is perfect, 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.

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

But winter 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.

Be sure to read our guide to planning a romantic winter getaway to Greenwich to start daydreaming!

Greenwich Events to Experience

With a multitude of Fairfield County 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:

  1. Focus on French Cinema
  2. Greenwich Town Party
  3. Bruce Museum Outdoor Spring Crafts Festival
  4. Greenwich International Film Festival
  5. Greenwich Wine and Food
  6. Outdoor Fall Arts Festival at the Bruce Museum
  7. Greenwich Holiday Stroll and Fair
  8. Greenwich Polo Club matches
  9. Labor Day Weekend

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

  1. Norwalk Oyster Festival
  2. Caramoor Summer Music Festival in Katonah
  3. Harvest Fest in New Canaan
  4. Oktoberfest at Bear Mountain

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

That’s easy!

staying in a romantic suite with a hot tub is one of the most romantic things to do in Greenwich, ConnecticutThe Stanton House Inn is a downtown Greenwich, CT, bed and breakfast inn. We offer all sorts of cozy Greenwich accommodations. From romantic honeymoon 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 in downtown Greenwich. 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.


Updated and republished May 29, 2020