How to Plan Quick Winter Weekend Getaways From NYC for Couples

laughing couple enjoying their quick winter weekend getaways from nyc by trainWinter in New York City brings the urge to bundle-up and avoid leaving home at all costs.

Thick sweaters, drinks that warm from the inside out, and any other means necessary to avoid cold are necessities this time of year.

But at the same time, getting holed-up in your apartment from November to March can leave you stir-crazy.

The solution?

A romantic getaway.

And New Yorkers are lucky enough to not even need a car to enjoy many of the options within a short distance of the City.

There are some fantastic winter weekend getaways from NYC for couples by train. But many New Yorkers limit their planning to such heavy hitters as:

  1. The Poconos
  2. The Hudson Valley and Upstate New York
  3. New Jersey
  4. Vermont

Have you considered somewhere less well-traveled (and therefore a more unique experience) and even closer?

Skip the long drive or train ride and visit downtown Greenwich, Connecticut. It’s just over the border from New York state, and the slowest local train only takes about 40 minutes to get you to the Greenwich Train Station.

But despite its proximity, it has just the New England experience you expect in our state.

In fact, Greenwich is one of the most romantic places for getaways for couples in Connecticut.

So, how do you plan a quick getaway from NYC this winter by train?

Read on.

Download a free copy of the official Greenwich, CT, Visitor’s Guide to easily find everything we mention here!

But first, a disclaimer.

Connecticut is just as cold as NYC in the winter. This is not the time of year to go exploring for hours outside, unless you enjoy skiing. In which case, enjoy your long trip to Vermont, Canada, or out West.

But you might as well take your fling somewhere new and exciting to enjoy fireplaces, hot drinks, and getting bundled up and cozy.

Besides, the only way to truly appreciate the warmth and feel alive this time of year is to experience a bit of cold, no?

Things to Do During a Winter Weekend Getaway From NYC for Couples

Greenwich, CT, has long been a destination for visitors. It’s still a fantastic getaway for New Yorkers, but there’s enough to do in the area to even attract international travelers.


While shopping on Greenwich Avenue can be appealing anytime of year, it’s especially a pleasure during the holidays, when it’s one of the best things to do in Connecticut in December.


Visit our guide to the best date ideas in Connecticut for more tips, some of the best winter activities in CT for your winter weekend getaway include:

Treat Yourselves to a Warm, Delicious Meal

Greenwich’s restaurant scene competes with New York City in diversity and quality. There are a total of 861 full-service restaurants in the area!

quick winter weekend getaways from nyc for couples by train are made infinitely better with a fireplaceTo narrow your choices down, we’ve included some of our favorites that feature fireplaces in their dining rooms. Because nothing fights the bitter winter cold like a warm meal by the fire. Here are some of our top picks for a romantic winter date night.

  • The Ginger Man on Greenwich Avenue is a warm and inviting tavern, especially in the winter, with its wood furnishings and large fireplace. While the extensive beer selection is a major draw, the food is just as excellent. Braving the cold for the 12-minute walk from the Inn will be well worth it.
  • Gabriele’s of Greenwich is a high-end Italian steakhouse only a 10-minute walk away from Stanton House Inn. A steak and a choice from their wine list should warm you and your travel companion right up.
  • Little Pub is a bit farther away in the next-door neighborhood of Cos Cob. Dark beams, tapestries, and a loud pub atmosphere make for a great place to enjoy a beer and traditional British food while connecting with pub patrons and each other. Little Pub is an 8-minute cab ride from the Inn.

While local cuisine is a highlight, there’s plenty more worth braving the cold for in the area.

Explore the Local Art Scene

Learn something new with your sweetheart at what is a cultural heart of New England in and of itself!


The Bruce Museum alone is a draw to Greenwich and only a 5-minute cab ride from Stanton House Inn. The Design District of Greenwich is also just a short walk from our inn, where you can find such galleries as:


Or walk down Greenwich Avenue to find the art galleries there. Be sure to stop at the Greenwich Art Council’s Benhdeim Gallery in the old Town Hall.

Local Theater near Greenwich

There are plenty of opportunities to see a show or other cultural attraction in Greenwich and around town! Take a look below and find the one that best suits you and your sweetheart:

  • Capitol Theatre: Located just over the border in Port Chester, NY, Capitol Theatre makes for a perfect date night. We recommend walking over to the Greenwich Train Station, riding over to Port Chester, and attending a show. You won’t even need a car!
  • Curtain Call: Another fantastic romantic evening activity in winter in Connecticut is seeing a show at Curtain Call in Stamford. This community theater can put many of New York City’s shows to shame!
  • Palace Theater: Another Stamford attraction. Palace Theater makes for an amazing date night activity. This old-time movie theater hosts plenty of shows throughout the year and is a quick cab or train ride away from Stanton House Inn.

Indulge in a Couple’s Spa Day

There’s nothing more romantic—especially in the winter—than enjoying a spa trip with your significant other. Luckily, Stanton House Inn, the most romantic B&B in Greenwich, is within walking distance of fantastic spas clustered on Greenwich Avenue in downtown Greenwich. A few of our favorite spas in Greenwich, CT include Posh Day Spa, Serenity Spa and Dream Day Spa.

Take a Connecticut Day Trip by Train

Regardless of the time of year, there’s nothing better than exploring an area, even if it requires braving the cold.


While we don’t recommend spending long hours outside, there are plenty of places for romantic Connecticut day trips within a short train ride of Greenwich. A few of our top suggestions for the most unique Connecticut attractions near us include:

  1. The Philip Johnson Glass House and New Canaan
  2. Historic South Norwalk and the Maritime Aquarium
  3. Westport, Connecticut, another one of the most cute towns in Connecticut


Be sure to read our guide to the best places to visit in Connecticut for winter vacation getaways for more destinations.

Experience Hygge at Stanton House Inn

a mug with a hot drink and a book are hygge exemplified on a romantic winter weekend getaway from nyc for couples by trainWhere else to enjoy hygge than in New England, the most northerly area on the American East Coast?

What is hygge?

It’s a Scandinavian term that loosely translates to a mood of coziness and comfort mixed with wellness, contentment, and conviviality.

And the Pearsons’ Swedish roots have helped them take an interest in incorporating hygge more into winter stays at our Connecticut bed and breakfast.

Join us and other guests in our common areas to enjoy some warmth from the environment and the community.

Wrap yourself in a blanket and cozy-up by the fireplace in our living room and watch the flames or borrow a book from our library. Enjoy a drink to warm yourself from the inside out while connecting with the team and other guests at the Inn.

If you’re not feeling sociable, take a long, hot bath in your room. The Brush Suite features an original clawfoot tub, though plenty of other rooms feature bathtubs in which to luxuriate. Or you can relax by your own fireplace.

But you’ll eventually need to brave the cold to explore the area.

While you’re welcome to spend the entire weekend at Stanton House Inn, it would be a shame to not see more of Greenwich.

After all, there are a surprisingly large number of things to do in Greenwich, Connecticut, in the winter.

Now, How to Plan the Best Winter Weekend Getaways from NYC for Couples by Train

snow on a pine branch on a quick romantic winter weekend getaway from nyc for couples by trainSound like a lot to plan?

It doesn’t have to be.

Follow our guide above to plan a perfect three-day romantic getaway to Greenwich and nearby towns. You can also download your copy of our free Greenwich, CT, Visitor’s Guide to keep everything straight while planning.


We are also proud to offer a Romance Package just for couples! This exclusive offer enhances romantic weekend getaways from NYC for couples with a bottle of champagne and chocolate-dipped strawberries. It’s the perfect addition to the pastoral, romantic escape of your dreams!


Check our availability today and book the getaway your special someone will remember for years to come!


Are you not sold on visiting Greenwich in the winter?


Then be sure to read our full list of the most romantic things to do in Greenwich, CT, if you’re open to planning a trip anytime of year.