Labor Day Weekend in Greenwich, CT: the Ultimate Guide

Labor Day is always the first Monday in September in the United States.

New York City unions started the holiday in 1882 as a way to celebrate their members being in unions.

But today, it’s a long weekend and the official close to summer in CT.

So enjoy summer’s last hurrah by taking some time to do more than sit on your couch in Greenwich, Connecticut.

Here’s the ultimate guide to enjoying Labor Day weekend in Greenwich, CT.

And get our full list of Labor Day weekend activities when you download the free Greenwich, CT, Visitors Guide.

What to Do in Greenwich on Labor Day Weekend

Greenwich is an easy, short drive or CT day trip on MetroNorth from the epicenter of the start of Labor Day in NYC.

But Greenwich, Connecticut, is both more relaxed, more bucolic, and significantly cooler than the City on a summer weekend.

So best avoid New York City and head to Greenwich for the weekend.

Summer Activities to Enjoy One Last Time in Greenwich

Think back to your youth, when summer was a never-ending wonderland of free time. Recreate that feeling with a weekend of relaxation, starting with a sunrise or two.

Witness a Summer Sunrise in Greenwich

I admit I had a hard time getting-up when I was young to witness a summer sunrise. But if you have the fortitude for it, have at it.

First light is shortly before 6am in Greenwich during Labor Day weekend, while actual sunrise is not until about 6:20am. You can always get up, pick a scenic location in downtown Greenwich to view it, then catch a couple more hours of sleep before breakfast.

Get One Last Beach Day in Greenwich

No long weekend would be complete without a trip to the beach. And the beaches near Greenwich, CT, are superb.

While all of them are open, Labor Day weekend is your last chance to take the ferry out of Greenwich harbor to enjoy Island Beach. Daily Island Beach ferry service ends immediately after Labor Day weekend every year.

Don’t forget to grab your beach park passes if you’re not a town of Greenwich resident. Or purchase our Connecticut beach vacation getaway package if you’d prefer we pick them up for you.

Week Before Labor Day Weekend Events

If you want to extend the Labor Day weekend to include Thursday evening (and Friday), check-out the Sheffield Island Lighthouse Clambake.

Sheffield Island Lighthouse Clambake

Clambakes are classic New England summer affairs. This particular clambake is held every Thursday in the summer, but the last one before fall seems a great time to experience it.

Take the train to the South Norwalk train station (or drive from Greenwich) and walk down to the Sheffield Island ferry landing on North Water Street.

From there, you’ll enjoy a roundtrip cruise to the Sheffield Island Lighthouse as well as panoramic views of Long Island Sound.

Once on the island, you’ll dine in the festive tented pavilion setup on the lawn, and enjoy a tour of the lighthouse if you’re interested. Dinner is provided by Chef Clyde Ripka of Ripka’s Beach Cafe.

The entire trip is priced at $65 or $79 per person, depending on what food you order in advance. Speaking of which, be sure to reserve your tickets for the Sheffield Island Clambake in advance, as lobster is not something you cook last-minute.

Labor Day Weekend Events

There’s plenty more to do later in the weekend. A few top picks are:

Greenwich Farmers Market

The Greenwich Farmers Market has met at the Arch Street parking lot in downtown Greenwich for over 25 years. While there aren’t a lot of farms left in Fairfield County, plenty of farmers make the trek down from other parts of Connecticut to sell their produce.

Poke around, chat with farmers, and pick-up some seasonal vegetables or fruits on Saturday.

See a Greenwich Polo Match

The next cocktail party you attend, tell them you saw a polo match. They’ll know you were visiting Greenwich.

Greenwich Polo has a match every Sunday through the summer. Gates open at 1pm, with matches running from 3 to 5pm. Tickets are $40 and up, but really this is one of those things you need to experience at least once.

Summer Events at the Bruce Museum

The Bruce Museum regularly changes its exhibits. For Labor Day weekend, visit the Bruce Museum to see the National Geographic Photo Ark. This traveling exhibit features the work of National Geographic photographer and Fellow Joel Sartore.

The National Geographic Photo Ark is an ambitious project committed to documenting every species in the world’s zoos and wildlife sanctuaries—inspiring people not just to care, but also to help protect these animals for future generations.

Labor Day weekend is the last one this exhibit will be at the Bruce Museum, so don’t miss out!

The Bruce the Museum will be closed on Labor Day, but the Bruce Museum Seaside Center at Greenwich Point Park will be open. Regular park admission rules apply for entry to the Seaside Center.

More Things to Do in Fairfield County on Labor Day Weekend

Stamford Labor Day Weekend Events

Next door to Greenwich, Stamford is an easy drive or train-ride away. And there are a couple events happening there the weekend of Labor Day worth checking-out.

St Leo Fair

Summer fairs are standard in New England. Every church holds one, especially the Catholic ones.

The St. Leo’s Fair is no different. It’s hosted every Labor Day weekend by St. Leo’s church in Stamford. Free admission to the church grounds gets you the chance to enjoy rides and carnival games, sample international foods, and gamble a little at the Bingo Parlor. Plus, there’s live music every night of the fair at 7:30pm.

Your New England summer is not complete until you’ve been to a fair to have a Pizza Fritta (locally pronounced, “pizza freet”).

Hours for the Fair will be 6pm to 11pm on Tuesday through Friday; and 2pm to 11pm on Saturday.

Once Endangered: The Return of Wolves & Peregrine Falcons

The Stamford Museum and Nature Center always has an interesting exhibit on-site. And Labor day weekend typically marks the end of that exhibition. So, you get one last chance to see it!

Sunset Cruises in Norwalk on Labor Day Weekend

If you missed Thursday’s clambake, you can at least get a sunset cruise or two in while you’re visiting Fairfield County.

Take the train or drive up to South Norwalk and grab a sunset cruise on the Maritime Aquarium’s research vessel to enjoy a 90-minute cruise timed with the sunset. Weather-permitting, you’ll get to watch the sun set over Connecticut, and enjoy the warm reflections of the summer sun’s last rays bouncing off of Long Island Sound. Added benefit is this one is BYOB, as well as your own food.

Westport Labor Day Weekend Events

Westport is a beautiful little town just a short train ride away from Greenwich.

Blue Views and BBQ Festival

Westport, Connecticut’s premier music festival delivers soulful, Southern-inspired food and music to the banks of the Saugatuck River in downtown Westport. Blues, Views and BBQ has long been a venue for introducing up and coming and local talent along with marquee headliners. Tickets are $15-90.

Even More Top-Rated Labor Day Weekend Activities

And of course, you’ll still be able to enjoy (though obviously, call ahead, just in case):

All of which is within walking distance of the Stanton House Inn.

And for even more Labor Day events across CT, be sure to read our full guide.

Where to Stay at the Stanton House Inn on Labor Day Weekend

Reserve a room with a view of our outdoor pool and enjoy one final swim for the summer.

Poolside rooms are:

And rooms with views of the pool include:

Plus, we’ll be able to make these recommendations and more for your visit each morning at breakfast in the dining room.

Not feeling a stay in one of our bed and breakfast rooms? Then read our guide to hotels in Greenwich. There’s sure to be a good fit!

What Not to Do in Greenwich on Labor Day (ie: What’s Closed)

Don’t worry, the list of things you can’t do on Labor Day in Greenwich won’t exactly be devastating:

Libraries
NY Stock Exchange
Banks
All U.S post offices are closed
Federal Offices
State Offices
Town Hall and municipal offices (so buy beach passes in advance)
Schools

Should be a relaxing weekend, quite frankly.

Be sure to read our full guide to things to do in September in Connecticut, to plan this coming weekend, or any weekend in September.

Updated and republished: June 13, 2023

Labor Day Weekend Greenwich CT Guide

What to Do in Greenwich on Labor Day Weekend