Friday October 2, 2026

26 Ways of Looking at a Black Man
7:00 pm
The Unitarian Universalist Congregation in Westport
10 Lyons Plains Road, Westport
Doors open at 6:40
10 Lyons Plains Road, Westport
Doors open at 6:40
A free concert by Grammy-nominated baritone Sidney Outlaw and pianist Piotr Kozlowsk, presenting the Connecticut premiere of 26 Ways of Looking at a Black Man, with music by B.E. Boykin and poetry by Raymond Patterson. An opportunity to hear a world-class performer presenting a deeply meaningful work that centers around Black artistry, identity, and lived experience. Free parking, handicap accessible. Light refreshments following the concert.
Saturday October 3, 2026

Earthplace Fall Festival
11:00 am – 3:00 pm
Earthplace
10 Woodside Lane, Westport
10 Woodside Lane, Westport
A day of family fun at Earthplace. The favorite fall tradition is back with hay rides, the corn pool, apple slingshot, pumpkin bowling, food trucks, animal encounters (including birds of prey), and more. Purchase tickets in advance here. Also, you can buy raffle tickets here and get three chances to win great prizes. The winner will be announced at the festival. All ticket proceeds directly support Earthplace.

Playing With Light
1:00 pm – 3:00 pm
Weston Public Library
A reception for an exhibition of photographs about light, shadow, reflection, color, and the little accidents that can turn an ordinary moment into something worth stopping for, when light becomes the subject. The exhibition runs from October 2 to November 28.
Saturday & Sunday October 3-4, 2026

Family Fun Carnival
12:00 pm – 6:00 pm
St. Francis of Assisi
35 Norfield Road
35 Norfield Road
The 16th annual carnival features a hayride (on Sunday afternoon), inflatables, games for children and adults, a silent auction and raffles, live music, face painting, crafts vendors, food trucks, and burgers, Italian sausage, hot dogs, cotton candy, pretzels, and drinks. A blessing of the animals takes place in the parking lot on Saturday at 11:00 am.
Sunday October 4, 2026

Native American Life
2:00 pm – 4:00 pm
Weston History & Culture Center
104 Weston Road
104 Weston Road
Dressed in traditional clothing, Drew Shuptar-Rayvis, a citizen of the Pocomoke Indian Nation, will discuss the contributions, struggles and sacrifices made by Algonkian peoples during the Revolutionary War, with demonstrations and artifacts. A free event planned for outdoors, but will move inside if necessary. Walk-ins are welcome, but you can register in advance.
Thursday October 15, 2026

Domestic Violence Awareness
12:00 pm
Weston Town Hall
The public is invited as Town of Weston officials proclaim October Domestic Violence Awareness Month in Weston with the Domestic Violence Crisis Center.

Weston Founders Day
5:00 pm
Town Hall Meeting Room
A celebration at Town Hall of Weston's founding, recognition of the Weston Celebrates America250 Advisory Group, and the dedication of a town time capsule.
Friday October 16, 2026

Aldrich Museum Tour
12:00 pm
Aldrich Contemporary Art Museum,
Ridgefield
Ridgefield
Join the Women’s Club of Weston for a guided tour of the Aldrich Contemporary Art Museum in Ridgefield, followed by a picnic lunch on its beautiful grounds. The Aldrich is the only museum in the state completely dedicated to contemporary art and is one of the oldest contemporary art museums in the U.S., dating back to 1964. To attend, please send a check for $37 made out to WCW, Inc., to Kathy Melrod, 10 Sasqua Trail, Weston, CT, 06883 by October 9.
Sunday October 18, 2026

Author Talk: The Life of Alice DeLamar
3:00 pm
Weston Public Library
Author Nona Footz talks about her book, “A Mansion of Her Own: The Mysterious Life of Heiress Alice DeLamar,” the story of a legendary figure in the history of Weston and the arts, a New York socialite who brought her refined taste and wealth to Weston in the 1930s, built a historic estate, bought properties that were leased to artists, donated land, and transformed the Cobbs Mill Inn into an upscale restaurant and bar. Registration is recommended. See our story for more.
Wednesday October 28, 2026

Witches of Connecticut
10:00 am
Weston History & Culture Center
104 Weston Road
104 Weston Road
Beginning a new Backstories & Breakfast speaker series, WHCC presents Rebecca Gavin, who will share stories of Colonial women and men accused, tried, and executed as witches and discuss how Connecticut ultimately controlled the spread of accusations. A light, seasonal breakfast will be provided. $10 for WHCC members, $15 for non-members. Register here.
