Events and Things to Do in Westport, CT

Seven Acres Montessori Virtual Prospective Parent Event

OCT

1

10:00 AM

Wilton, CT

Seven Acres Montessori is an independent non-profit school accredited by both The Association Montessori Internationale and The...

LIVE WEBINAR: Building Your Child’s Independence: Executive Function Coaching at Home and at School

OCT

1

7:00 PM

Litchfield, CT

Any adult who has helped a learner—formally or informally—has access to two useful voices: a “Teacher Voice” that provides...

Large Estate Sale - Weston

OCT

2

9:00 AM

15 Birch Hill Rd, Weston, CT

Large Estate Sale - Weston This lovely Barn Style Home is filled with treasures. Lovely Antiques and vintage items. Signed...

Fun Petite Downsizing Sale

OCT

2

12:00 PM

Fairfield, CT

FUN PETITE DOWNSIZING SALE FAIRFIELD, CT • BEACH AREA   FRIDAY, OCT. 2nd & SAT OCT. 3rd  TIME: 12–4 PM Designer Clothing & Home...

26 Ways of Looking a Black Man: Free concert with Sidney Outlaw at UU Westport

OCT

2

7:00 PM

The Unitarian Universalist Congregation in Westport, 10 Lyons Plain Rd, Westport, CT

Please join us in welcoming Grammy-nominated baritone Sidney Outlaw for a special evening of music at UU Westport. Accompanied...

College Day- A Free Local Event

OCT

3

9:00 AM

Weston-Redding-Easton, CT

Families lose the college admissions game without ever realizing it.  Not because they weren't smart. Not because their kid...

Fun Petite Downsizing Sale

OCT

3

9:00 AM

Fairfield, CT

FUN PETITE DOWNSIZING SALE FAIRFIELD, CT • BEACH AREA   FRIDAY, OCT. 2nd & SAT OCT. 3rd  TIME: 12–4 PM Designer Clothing &...

PopShop Market at Westport Museum for History & Culture

OCT

3

10:00 AM

Westport Museum for History and Culture, 25 Avery Pl, Westport, CT

Saturday, October 3, 2026 Time: 10:00 AM–4:00 PM Location: Westport Museum for History & Culture 25 Avery Place, Westport,...

Fairfield Celebrates Down Syndrome

OCT

3

10:00 AM

909 Reef Rd, Fairfield, CT

It's a day for individuals with Down syndrome and other neurodivergent individuals, their families and friends to celebrate...

Darien Commons Pumpkin Parking Lot Party

OCT

3

12:00 PM

126 Heights Rd, Darien, CT

Get ready for an afternoon of fall fun for the whole family at our Pumpkin Parking Lot Party, proudly sponsored by BMW of...

Strides for Strength

OCT

4

8:00 AM

Seaside Park, 1 Barnum Dyke, Bridgeport, CT

Strides for Strength walk & 5K to benefit the patients and programs of Norma Pfriem Breast Center part of Smilow Cancer...

The Bard At Bristow - An Immersive Stroll

OCT

4

11:00 AM

New Canaan, CT

Overview Immerse yourself in William Shakespeare’s timeless tales on a scenic stroll through Bristow Bird Sanctuary....

First Folk Sunday

OCT

4

12:00 PM

Saugatuck Rowing and Fitness Club, 521 Riverside Ave, Westport, CT

Westport, CT – Westport tends to produce top-notch musicians. Many have moved away and yet many want to return when invited to...

Open House - PreK-12

OCT

4

1:00 PM

King School, 1450 Newfield Ave, Stamford, CT

Join us for our Open House on Sunday, October 4 from 1:00-3:00 p.m. Discover the power of a King education firsthand. Learn...

Walk The Extra Mile With Rach's Hope!

OCT

4

3:00 PM

Westport, CT

💙 WALK THE EXTRA MILE WITH RACH’S HOPE! 💙 Join us on Sunday, October 4, 2026 at 3:00 PM at Compo Beach in Westport, CT for the...

Fairfield Harvest Market October 17th - Vendors Being Accepted

OCT

17

10:00 AM

611 Old Post Rd, Fairfield, CT

The Fairfield Chamber of Commerce is happy to announce that its annual “Fairfield Harvest Market” event, will be held on the...

FCDS Open House - Saturday, October 17

OCT

17

10:00 AM

Fairfield Country Day School, 2970 Bronson Rd, Fairfield, CT

Confidence. Curiosity. Character. It all starts with the right foundation. Discover how Fairfield Country Day School helps boys...