What to Do for Labor Day Weekend in Westchester County

For those of you who can’t or would rather not send off summer with the traditional outdoor blowout, here are four of our favorite alternative celebrations this weekend.

Adobe Stock / Mark

Westchester has a lot to offer this Labor Day weekend. We’ve compiled a list of events and activities to keep you and your family entertained over the next few days.

It’s hard to believe, but Labor Day weekend is practically here in Westchester. Kick off the long weekend in style with an abundance of activities around the 914. Browse through our guide for inspiration so you’re ready to go when your OOO message kicks into gear.

WGGCon 2023

Croton Point Park, Croton-on-Hudson
Labor Day weekend

Calling all gamers! The Westchester Gaming Group will be holding its WGGCon this weekend at Croton Point Park. Kicking off on Friday, there will be a hot dog cart at 6 p.m., and the movies Princess Bride and Galaxy Quest will show after dark. Saturday’s festivities start in the morning with some games, a barbecue at 5 p.m., and a game auction. Bright and early on Sunday, attendees can run the Croton Point Pointless 5K to get their heart rate up. Gamers are encouraged to pack their favorite games to play. Check out the website for the full schedule of activities.

- Advertisement -

Kykuit Tours

Kykuit, Sleepy Hollow
September 1-4, 10:30 a.m. – 3:30 p.m.

Go outdoors while the weather still permits and spend your Labor Day exploring the charming Kykuit home. Sign up for a tour anytime between 10 a.m. and 5 p.m.; tickets cost between $20 and $65. Learn all about the four generations of Rockefellers who lived in this home built between 1906 and 1913. The estate offers three tours: the classic tour, great for first time visitors; the grand tour, which includes the classic tour plus extra time in the gardens and art galleries; and the selected highlights tour, which includes the main floor, inner garden, and west terrace.

2023 Hudson River Arts & Crafts Festival

Senasqua Park, Croton-on-Hudson
September 2, 11 a.m. – 5 p.m.

This year, the Hudson River Arts & Crafts Festival extends its hours due to the success it saw last year. This is an outdoor festival with gorgeous views of the Hudson, during which local artisans can set up shop and sell their handmade goods. There will be crafts of all kinds plus free parking and admission. The rain date is September 3.

- Partner Content -

Lawn Bar Party

Goosefeather, Tarrytown
September 2-3, 12-8 p.m.

Goosefeather, Chef Dale Talde’s restaurant located at the Tarrytown House Estate, hosts a friends-and-family lawn bar party from noon to 8 p.m. There are no tickets for this event, but all food and beverages will be available for purchase, and there will be lawn games.


View this post on Instagram


A post shared by Goosefeather (@goosefeatherny)

Labor Day Firework Shows

Playland Park, Rye
September 2-3, 8:30 p.m.

- Advertisement -

Celebrate the holiday weekend at Playland this Saturday and Sunday evening. Starting at 8:30 p.m., there will be a festive firework display along the Long Island Sound.

Lyndhurst Ramble Tour

Lyndhurst Mansion, Tarrytown
September 3

The historic site offers a walking tour each Sunday up until October 1, making it the perfect destination during Labor Day weekend. Visitors have the chance to tour the Gothic Revival estate, which overlooks the Hudson and sits on 67 acres. The walk makes stops at the unglazed Lord & Burnham steel-framed greenhouse, the oldest regulation bowling alley in the U.S., and the 1911 unrestored pool building. The tour lasts two hours and starts at the Welcome Center. Tickets are $32.

Songs for Labor Day: Workers’ Struggles, Organizing, and Unions 

St. Paul’s Church Historic Site, Mt. Vernon
September 4, 1 p.m.

Dive into the history behind Labor Day this holiday weekend. Learn about the labor movement and how it still has an impact on our lives to this day. Music historian Robert Cohen will explore the history of the labor movement through recordings, songs, and commentary. This event is free.

Vintage & Artisan Flea Market 

Westchester Ave, Pound Ridge
September 4, 10 a.m. – 4 p.m.

Pound Ridge will hold its second annual vintage flea market during Labor Day weekend. Shop for unique pieces and local artwork from the 50 vendors who will be in attendance. Alex Cano, Dan Ziotnick, and Jones Music NYC will provide the music, and seven food trucks will serve up grub.


View this post on Instagram


A post shared by Shop Pound Ridge (@shoppoundridge)

Related: These 4 Westchester Landmarks Are Reopening for Historic Visits

Our Best of Westchester Party is July 24!

Our Westchester Home Design Awards event is June 26!

Our Wine & Food Festival returns June 4-9!

Our Wunderkinds event takes place on May 23!

Our Best of Business Ballot is open through May 15!

Our Healthcare Heroes Awards event takes place on May 9!

Our Westchester Home Builders Awards take place on April 4!

Our Diversity, Equity & Inclusion Forum is March 14!

Unveiled: A Boutique Bridal Brunch is February 25!

Holiday flash sale ... subscribe and save 50%

Limited time offer. New subscribers only.