Concierge Calendar - October 2026

October 2026 Calendar - 3 column








October Events




Curated by the

KMS Team at Compass


October brings more to Fairfield County than pumpkin spice and Halloween festivities. We have gathered a selection of events and creative ideas to inform, entertain, and inspire you, helping you and your family find even more reasons to love your home.


Simply click any image below for more information.

October 1

TRENDS & STYLES

Tonight’s outstanding Fall Fashion Show, presented by Jennifer Butler, supports the programs and services of the Fairfield Library.

October 2

A Radio Play

Experience the golden age of radio with three

Hitchcock thrillers, reimagined as a 1940s broadcast by Westport Community Theatre.

October 3

Drop in, 12-4pm

Please join us for seasonal refreshments and an opportunity to view the renovations of the historic Westport Bank & Trust Building.

October 4

carnival

The 16th annual St. Francis of Assisi Family Fun Carnival is this weekend, noon to 6 pm. Rain or shine, it's a favorite Weston activity!

October 5

MOMS UNHINGED

This popular comedy show is in Fairfield for a special performance. Enjoy a hilarious night of motherhood, marriage, and midlife sagas.

October 6

HEALING PROCESS

Ecopsychologist Jennifer Boyd leads this Verso U course exploring the evolving field of psychedelic-assisted mental health healing.

October 7

GIRLS ON THE RUN

Girls, grades 3–7, can participate in this weekly program, building endurance and friendships. Running a 5K is the culminating, celebratory event.

October 8

night out

Weave and decorate a Cherokee single-wall basket out of reeds while hanging out with friends. Bring drinks and snacks, Earthplace has the rest covered!


October 9

WRISTBAND NIght

The New Canaan Nature Center is hosting its Fall Fair this weekend. To skip the ticket lines and head straight for the rides this evening, pre-order your wristbands!

October 10

Thrills & Chills

Special weekly event at Adventure Park features changing themes plus 15 trails, 44 zip lines and 190 treetop platforms, to challenge all skill levels.

October 11

Fall Fav

Today's arts festival features local artists, exhibits, activities and a Young Entrepreneurs Market, showcasing kids creative ventures.

October 12

ART ~ History

Kids participate in an art project inspired by creativity, nature, lore and Indigenous culture traditions in this morning camp at MoCA.

October 13

Creativity

Teens decorate a sugar pumpkin, making it spooky, silly, or sweet. The library will display them and the public will vote for their favorite.

October 14

LiBRARY ROCKS

Playing in the Wilton Library Brubeck Room tonight, The Lonetown Boys bring the timeless music of Hank Williams to life.

October 15

Networking

"Leash" new business opportunities or "fetch" new local contacts at this after-hours event sponsored by Wilton Chamber of Commerce.

October 16

Nueva Miriachi

Experience the vibrant spirit of Mariachi Herencia de México as they return to the Quick Center for an evening of masterful artistry and chart-topping hits.

October 17

treasure hunt

Following last spring's success, the Nolan Team at Compass is hosting another Town-wide Tag Sale on Saturday, October 17. Join us as a shopper or seller!

October 18

SUNDAY FUNDAY

Head to Wakeman Town Farm for a family-friendly event with live music by Third Rail, lawn games, bubbles, animal encounters, and crafts for the kids.

October 19

monday meander

Meet under the arches at the Pequot Library for a 45-minute walk through the historic Southport village neighborhood.

October 20

WEDDed BLISS?

Napoleon at Pemberley blends Jane Austen’s elegant world with adventure in a comedy about marriage, ambition, and destiny.

October 21

Ah-Beetz

New Haven Museum's exhibit traces the origin of the city’s “Big 3” pizzerias & explores the relationship of family, food and community.

October 22

Abstraction

Artist Melissa Benedek teaches expressionism using color, movement, and music to help your paintings unfold naturally. Adult class.

October 23

Spirits of 1776

At Lachat, the American Revolution is unfolding and danger lurks in this interactive experience, with fallen soldiers & and other evil spirits.

October 24

Halloween Fest

Calling all little goblins and ghouls! Stepping Stones Children's Museum invites you to B a fun-filled event for the whole family.

October 25

ON THE GREEN

Fairfield’s Halloween event features trick-or-treating, art, food, and a bounce house, presented by the Town and local organizations.

October 26

HUNTERS MOON

Celebrate Bat Week with a guided night hike, observing nocturnal wildlife. View autumn constellations too, at Earthplace after dark.

October 27

POT OF FONDUE

Settle into fall with a wine and cheese event. The Fairfield Cheese Company takes you on a tasting journey through the French Alps.

October 28

ANNUAL PARADE

Trick-or-treat down Main Street to Veteran's Green for a Monster Mash with DJ Kenny Michaels, hosts - PAL and Westport Town Hall.

October 29

Scarecrow-ooza

Stop by the Morehouse Field in Easton to view the town's creations lining the split-rail fence. Come back on the 30th for trunk-or-treat!

October 30

Costume READY?

Fairfield Center Stage and SHU Community Theatre co-produce this cult classic, with a live cast performing in front of the screen.

Newcomer or long-timer, we hope you all find something new to enjoy near home this month.

Compass Connecticut, LLC is a licensed real estate broker. All material is intended for informational purposes only and is compiled from sources deemed reliable but is subject to errors, omissions, changes in price, condition, sale, or withdrawal without notice. No statement is made as to the accuracy of any description or measurements (including square footage). This is not intended to solicit property already listed. No financial or legal advice provided. Equal Housing Opportunity. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions.
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