Fall is such a wonderful season to be outside as a family.
Pop by a local farm to pick apples or pumpkins. Jump on a hayride.
However, if you are looking for a few more ideas besides apple and pumpkin picking, I’ve got you covered!
Check out my picks for Fall Family Activities in the Hudson Valley, NYC, Westchester County and Connecticut.
Fall Activities Hudson Valley
New York Renaissance Faire, Tuxedo, NY
When: Saturdays, Sundays, and Labor Day, August 26, 2023 to October 8, 2023
Details: If you’re looking for something Fall activities in the Hudson Valley, check out the New York Renaissance Faire!
In Tuxedo, NY, not far from Westchester or Fairfield Counties, lies a magical faire sure to enchant its visitors with themed games, rides, performances, and of course, jousts.
Kids will love seeing the costumed performers and attractions from days of yore.
Tickets can be purchased in advance and used any day during the Faire’s run.
Adults tickets cost $42 and children aged 5 through 12 are $18 (Ages 4 and under are free).
Tickets include access to all entertainment and performances.
Rides, carnival games, and food vendors are an additional fee.
Fall Activities Westchester County
Chappaqua Children’s Book Festival, Chappaqua, NY
When: Saturday, September 30, 2023 from 10am to 4pm
Details: Your kids will love this favorite Fall activity in Westchester County.
On September 30th, head to the Chappaqua Train Station with your kiddies to meet over 180 of their (and your) favorite children’s authors and illustrators at the 10th annual Chappaqua Children’s Book Festival!
The list of attending authors and illustrators is truly remarkable.
Author of the New York Times #1 bestselling Magic Tree House series, Mary Pope Osborne, will be at the Chappaqua Children’s Book Festival.
The event is the LARGEST children’s book festival in the metropolitan New York area!
Admission is FREE.
Authors will be selling copies of their books for autographs.
Fall Activities Connecticut
Westoberfest Fall Festival – New England Craft Beer Tasting, Westport, CT
When: Saturday, October 14, 2023 from 2pm to 5pm
Details: In Munich, Germany, fall is synonymous with Oktoberfest and while the famous festival is actually celebrated there from mid-September to early October, here in the States, the celebrations tend to happen a little later in October (whoops!)
If you are hoping to celebrate Oktoberfest this year without having to leave the kids at home, consider the Westoberfest celebration happening on October 14th at the Elm Street Lot in Westport, CT.
There will be craft beer tasting, delicious foods from Walrus Alley, Little Pub, LobsterCraft and more!
There will be over 60 varieties of craft beer at Westoberfest!
Enjoy live music by “One Bad Oyster”.
To entertain the smallest guests, there will be a family-friendly section with design-your-own MoCa Westport Halloween candy tote bag art projects with MoCA Westport, face painting by Fancy Faces Face Painting, pumpkin decorating activities with The Artists Collective of Westport, Pete and Chris Amusements with amusements and games, bubble show and much more!
Be sure to buy your tickets in advance to save!
Advance ticket prices: Single for $45, Social pack of 10 for $400 and Designated Driver for $10
For on-the-day tickets, Single for $55
The event is rain or shine (beer tasting area will be tented) and will take place at Elm Street in Westport, CT.
Westoberfest is the perfect Fall activity in Connecticut for families!
Set Sail: The OGRCC Annual Sailboat Regatta, Old Greenwich, CT
When: Sunday, October 15, 2023 from 1pm to 4pm
Details: If you are looking for things to do in Connecticut this Fall, what about joining a sailboat regatta? Kids (and adults) of all ages will enjoy this favorite Connecticut Fall Activity!
Back for its 59th year is the annual Model Sailboat Regatta in Old Greenwich, CT’s Binney Park.
Model sailboat enthusiasts of all ages can come join the fun.
Categories for homemade boats, motorized and remote-controlled boats are spread out throughout the afternoon.
Bring a picnic lunch and join in on the fun!
Tickets to join a sailboat regatta cost $10 per entry with a $25 family maximum and all the money raised will go to the OGRCC’s scholarship fund that supports 65 families each year.
Tickets can be purchased in advance here.
Fall Activities: NYC
Governors Island, New York, NY
When: Governors Island is open year-round. The South Island Park is open until 6pm daily.
Details: While not located in the suburbs, Governors Island is just as idyllic and tree-lined as a suburb, but with the level of culture and arts you expect from NYC.
The island is accessible by a quick ferry ride from Lower Manhattan or Brooklyn, and visiting in the fall is perfect since there is a lot of walking and outdoor time involved.
There is a ton going on, especially on weekends, on Governors Island.
Governors Island is a spectacular and exceptional destination for transformative public art, unforgettable events, cultural and educational programming, and recreational activities for people of all ages.
There are hammocks to lie in, wooden climbing structures to play on, a Slide Hill to race down and so much more.
Activities, public programs and events will be updated here on an ongoing basis.
No matter how you spend your day at Governors Island, it is so worth the visit.
You may also be interested in:
Top 5 Places to Go Apple Picking in the New York Tri-State Area
Pros and Cons of Cruising from New York
20 Family-Friendly Indoor Activities in the NY Tri-State area
Private School versus Public School
Seriously, Sam? 10 Simple Rules to Throw Your Child a Birthday Party that Doesn’t Suck
About Marissa Millman
A corporate lawyer by day and blogger at Donuts at the Disco by night, Marissa Millman is so excited to finally let her more creative side shine as a blogger. Marissa was born on Long Island and spent her entire life in New York before meeting her CT born husband, Michael, in 2006 and eventually moving with him to Greenwich, CT in 2011. Together, they have two CT-born little ladies, and over time, their passion for exploring and experiencing all that’s around them has become a family affair. Marissa started her blog in the summer of 2018 to share what her family is up to in hopes that it may inspire other families to do some of those same things. Website: Donuts at the Disco. Instagram and Facebook @donutsatthedisco
About Suburbs 101
Suburbs 101 is an online lifestyle guide for the New York Suburbs of Westchester County, Long Island, Fairfield County and Northern New Jersey. Get the inside scoop on what it’s really like to live in the New York suburbs through our weekly interviews with local suburbanites and features on Food, Fashion, Home, Travel, and Local Events. Be sure to Follow Us on Instagram, Like Us on Facebook and subscribe to our Monthly Newsletter.