Travel like a local.

Podcast, Reedy Press

Putnam Cottage, Bruce Museum & Connecticut Art Trail in Greenwich, Connecticut

Best things to do in Greenwich Connecticut - Stasha Healy - Roebling Bridge by Marlene Pixley

The Roebling Bridge, designed by the firm that also designed the Brooklyn Bridge in NYC. Photo by Marlene Pixley

I’m really excited to interview author Stasha Healy, author of Secret Connecticut about Greenwich, Connecticut. Stasha’s tips for the best things to do in Greenwich are awesome because she spent her teenage years in Greenwich, moved away for college, then came back to start a family. She loves how the locals are well-educated and philanthropic, supporting education and the arts.

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Best things to do in Greenwich Connecticut - Stasha Healy - Durston Saylor Greenwich Historical Society

Durston Saylor Greenwich Historical Society

Greenwich, Connecticut

We share a lot of resources and local suggestions in today’s podcast, but you should also check out Town of Greenwich, the local visitor’s bureau. They are a wealth of information and can help you plan an itinerary based on your time, budget, and interests.

If you’d like to learn how to travel for free using airline miles and hotel points, check out my free 7-day email course.

Best things to do in Greenwich Connecticut - Stasha Healy - Bruce Museum w dino

The Bruce Museum with a dinosaur statue outside

Getting around Greenwich

The local airport is Westchester County Airport (HPN), which is about a twenty-minute drive to downtown. Or you can fly into Newark Liberty International Airport (EWR) and take the Amtrak to Stamford, which is the town next to Greenwich. You can catch a cab or rideshare from the train stop to the city.

Stasha says that, depending on your itinerary, you might want to rent a car. For the best offers, visit Avis, Budget, or Hertz.

Uber and Lyft are excellent ways to get around. You can also use the Greenwich Taxi company as well.

When you only need a car for a couple of hours, you can rent by the hour with Zipcar. Join now to get $25 loaded into your account.

Best things to do in Greenwich Connecticut - Stasha Healy - Greenwich polo

Catch a polo match during your visit.

Places we talked about on the podcast

Here is a map of all of the places we talked about on the podcast episode with Stasha Healy about Greenwich, Connecticut. You can zoom into the map and click on each dot to explore the city.

  • Red dots = best places to eat in Greenwich, Connecticut
  • Green dots = best things to do in Greenwich, Connecticut
  • Yellow dots = best places to stay in Greenwich, Connecticut

Who is Stasha Healy?

Anastasia Mills Healy is a career travel writer and editor, formerly on staff at Condé Nast Traveler, Fodor’s, and Travel Agent. She’s been a freelance writer and editor for more than a decade for publications including Time Out and Frommer’s, and she also provides content for travel industry clients and other businesses. An award-winning writer, Stasha is a proud member of professional organizations including the Society of American Travel Writers.

A Connecticut resident on and off since 1980, she resides in Greenwich where she’s working on a novel. Stasha has been to 64 countries (goal is 100) and all 50 U.S. states (yes, Connecticut is one of her favorites!). Stash took her intimate knowledge of Connecticut to write her book, Secret Connecticut: A Guide to the Weird, Wonderful, and Obscure, for Reedy Press.

Best things to do in Greenwich Connecticut - Anastasia Mills Healy

Here are a few articles that she’s written:

You can connect with Stasha on her website and on Twitter, Facebook, and Instagram. You can support this podcast and our guest by buying her book, Secret Connecticut, through our Amazon affiliate link.

Big thanks to today’s affiliate partner – Acorns

With Acorns, you can invest spare change automatically on every purchase that you make. With your registered cards, purchases are rounded up to the next dollar and added to your investment account. When you shop at participating retailers, you can also earn bonus dollars called “Found Money.” Acorns is a great way to build up your travel fund automatically.

I’ve been using Acorns for years, and I love how easy it is to use. For a limited time, when you sign up at, we’ll both earn $5.

Best things to do in Greenwich Connecticut - Stasha Healy - Island Beach

Enjoy the warm Greenwich summers relaxing on Island Beach

Stay tuned for our next episode

Listen to the next episode when Victoria Greene of TORsAdventures – Travel like a Billionaire shares the best things to do in Whidbey Island, Washington. In this episode, Tor and I talk about exploring Fort Casey State Park, whale watching in Puget Sound, and hiking at Price Sculpture Forest. We hope you’ll join us when We Travel There.

What’s your favorite part of Greenwich? Send us a Tweet, let us know in the comment section below, or continue the discussion in our Facebook group!

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To see which cities we’ve interviewed and scheduled, please visit If you’d like to be a guest on the show, please submit an application at

Related episodes

Greenwich is just outside of New York City. Listen to our episodes for NYC and the surrounding area to learn what else there is to do nearby.

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