Passionate About the Community
and the Moms Who Live Here

A Mom’s Guide to Fairfield County :: September 2018

It’s hard to believe that the summer is coming to a close – it’s September! We love summer, but we also can’t wait to wear boots, eat and drink pumpkin everything, and go apple picking! Here is a list of family fun events to enjoy this month. This is in no way intended to be a comprehensive event guide, so if you have suggestions or any great events that we’ve missed, please leave a comment to let us know!


  • All Month :: Find an adventure at Discovery Adventure Park. This month’s activities include End of Summer Bash on September 9 and Glow in the Park on September 14 and September 28.
  • All Month :: On different days throughout the month, residents of Fairfield, Trumbull, Stratford, and Monroe residents can enjoy admission to the Beardsley Zoo for only $5.00 per person with ID. You will get to meet and greet local officials as well as business and civic leaders, your friends, and your neighbors. 
  • Monday, September 17 – Sunday, September 23 :: Enjoy delicious food at discounted prices at Black Rock Restaurant Week.
  • Friday, September 21 – Sunday, October 14 :: Watch Legally Blonde The Musical at the Downtown Cabaret Theatre. 


  • Sunday, September 9 :: Have fun with the family at Kids Day 2018, hosted by the Brookfield Volunteer Fire Company. They will have trucks on display, kids activities and fire truck rides. Amber alert, Brookfield Police and Brookfield Parks and Recreation will be on hand as well as other local agencies. Lifestar helicopter will be on display (weather and call pending). There will also be a stuff a truck to benefit the Brookfield Food Pantry.



  • Saturday, September 8 :: Party in the Park at Owen Fish Park for a family fun day to raise money for the Four Corners Beautification Project. There will be relay races, giant inflatable waterslides, face painting, bocce and cornhole, a homerun derby, a live band, food trucks, and more.
  • Friday, September 14 – Sunday, September 16 :: Celebrate the end of summer with Our Lady of the Assumption Church’s SeptemberFest.
  • Saturday, September 15 :: Head over to the Fairfield University Bookstore for a free Batman comic book to celebrate Batman Day.
  • Saturday, September 15 – Sunday, September 16 :: Get your color on and rally for a 5K run/walk and stroll to benefit The Kennedy Center Autism Project. There will be lots of things for the kids to enjoy, including Casey Carl’s Bubblemania, Bounce House, Face painting, Sensory Tent, Games, Entertainment and Much More. There will also be Food Trucks.
  • Sunday, September 30 :: Head over to the Fairfield Food Truck Festival, where there will be more than 25 trucks serving great food on Jennings Beach.


  • Thursday, September 13 – Saturday, September 15 :: Find treasures at The Tiny Tots Kids Consigment Fall Sale.
  • Saturday, September 15 – Sunday, September 16 :: Join Audubon Greenwich for a family-friendly nature festival to celebrate the fall season and annual  migration of raptors at the 20th Annual Fall Festival & Hawk Watch
  • Saturday, September 21 – Sunday, September 22 :: Celebrate community, charity, food, beverage and more at the Greenwich 2018 Wine + Food Festival presented by PepsiCo
  • Sunday, September 23 :: Go Wild! in support of The Greenwich Land Trust and enjoy activities and entertainment for all ages, including tasty treats from local food trucks, live music as well as hot air balloon rides, a petting zoo, arts & crafts, and the ever-popular bungee trampoline. 


  • Saturday, September 8 – Sunday, September 9 :: Kick-off New England’s fall season at the St. Peter’s Annual Apple Festival.
  • Sunday, September 23 :: Party in the Park at Wolfe Park to support the Monroe Playground Foundations – Kids Kreation Rebuilding Project. There will be delicious food, a 9-hole mini golf course, bounce houses, games, face painters, a DJ and a live band.

New Canaan

  • Saturday, September 15 :: Celebrate the Fall Cider Season at New Canaan Nature Center for Cider Saturday. Enjoy an early autumn afternoon of family fun with cider press demonstrations, old-fashioned games, a pumpkin scavenger hunt, seasonal harvest crafts for kids, baked apples, and corn bread on a stick! 



  • Thursday, September 6 :: Enjoy free admission and activities at Stepping Stones Museum from 5-8 p.m.
  • Friday, September 7 – Sunday, September 9 :: Head over to Veteran’s Memorial Park for three days of continuous family-friendly activities and entertainment at the 40th Annual Oyster Festival. Children under 5 years old are free!
  • Sunday, September 30 :: Join the Norwalk Historical Society at Mill Hill Historic Park for a celebratory event honoring the lives of the brave women who worked on the home front during WWII for Rosie the Riveter Day. Free event!


  • Sunday, September 23 :: Watch the Great Pumpkin Weigh Off at Ballard Park while also enjoying music, kids activities, pumpkin decorating contest, exhibitors, shopping and farm stands!


  • Saturday, September 15 – Sunday, September 16 :: Shop craft and artisan boutiques at Arts & Crafts on Bedford. Don’t miss the Imagination Station with “hands on” activities for kids including farm animals, chalk the walk, face painting, crafts and more!
  • Thursday, September 27 – Sunday, September 30 :: Join the community of the Greek Orthodox Church of the Archangels for their annual Greek Fest! Come experience the flavors, sights, sounds and traditions of Greece in Stamford. Fun for the whole family, including a kids carnival!
  • Sunday, September 30 :: Enjoy interactive hands on STEM experiences and displays from local teachers, students, parents, businesses and STEM related organizations at Mill River Park for Stamford STEMfest.


  • Saturday, September 22 :: Touch-A-Truck with St. James School. There will be over 60 amazing trucks on display, including swat vehicles, bucket trucks, garbage trucks, fire, rescue, military and more.


  • Saturday, September 8 :: Join LIVFREE for a movie night to bring the community together to bring awareness to Childhood Cancer Awareness Month. They will be showing Disney’s COCO and will have a variety of activities from 4PM to 7PM including games and food trucks. The movie starts at 7PM. 
  • Sunday, September 16 :: Peruse over 30 juried crafters, 20 fine artists, authors, Community booths, food trucks and food vendors, a Children’s Creative Center, and enjoy local entertainment at the 40th Annual Trumbull Arts Festival. All activities are free of charge.
  • Friday, September 21 – Sunday, September 23 :: Shop Just Between Friends at Insports Center to find some great deals on new and gently used children and maternity items.
  • Saturday, September 29 – Sunday, September 30 :: Head over to the 42nd Annual Apple Festival at Christ Episcopal Tashua. There will be their famous homemade pies, gourmet quiches and baked goods, a variety of arts and crafts from local and out of state artisans, locally grown apples, cider, pumpkins, gourds, cornstalks, and colorful mums and other fall plants, plus children’s games, raffle prizes, entertainment, local non-profits and more.


  • Saturday, September 15 :: Gather the kids and head over to the Emmanuel Church 112th Family Fair. The event is free and features great eats, entertainment, kids activities and more! 


  • Saturday, September 8 :: Experience a Slice of Saugatuck for the 7th annual food tasting and retail experience including family fun and live music.
  • Sunday, September 29:: Welcome the season of crisp air, fresh apples, and colorful leaves at terrain’s annual Autumn Bounty Festival! They’ll be hosting a Saturday celebration with live music, crackling fires, and lots of local friends and artisans from Phoencia Flea.

Just Outside of FC – Valhalla, NY

  • Sunday, September 30 :: Join the Ronald McDonald House of Greater Hudson Valley for the 4th Annual Dylan J. Hoffman Memorial Walk and Family Fun Day. The walk will be a leisurely stroll around the campus of the Westchester Medical Center (approximately a 1.2 mile lap) and then enjoy fun family activities! Dylan lived a short life, but his memory and spirit are alive and well. This event, hosted by the House in conjunction with the Hoffman Family, is a celebration of his life and the thousands of families who have stayed with the House since is inception. 

Looking for more fun?

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