Saturday October 17, 2026
Pumpkin Fest 2026
1:00 pm – 3:00 pm
Wilton Historical Society
224 Danbury Road,
Wilton
See demonstrations of open hearth cooking and blacksmithing, play fall-themed lawn games, or explore the museum campus and complete the pumpkin scavenger hunt, all with complimentary cider and donuts. Pick out a pumpkin to buy, then visit the decorating station. Small gourds and mums also on sale. $5 per person, free for Wilton Historical Society members. Tickets available at the door and in advance here to save time.
Woodside Bash
6:00 pm – 9:00 pm
Earthplace
10 Woodside Lane, Westport
The annual party under the stars is an evening of dinner, drinks, dancing, and a cozy campfire. The festivities kick off with a cocktail hour celebration featuring axe-throwing, signature drinks, live music and surprises. Only for adults 21 and above. Tickets, $150, are available here.
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.
Monday October 19, 2026
Candidate Debate: Congressional
7:00 pm – 8:30 pm
The Westport Library
The Lower Fairfield County Leagues of Women Voters host a debate between Rep. Jim Himes (D), Dr. Michael Ted Goldstein (R), and Benjamin Wesley (I), candidates for U.S. Representative for Connecticut’s 4th Congressional District. The event is free, but registration is required. The debate will also be livestreamed on YouTube.
Thursday October 22, 2026
The History of Beer
7:00 pm
Weston Public Library
Community Room
Illustrator, author and Advanced Cicerone Em Sauter presents the role of beer and brewing in American history, from the landing on Plymouth Rock to the modern craft brewery movement. Also enjoy four ounces of three different beers, plus pretzels. Ms. Sauter is the founder of Pints and Panels, a website focusing on visual drinks education. Adults only, age 21 and over. Photo ID required. Registration is too, as drop-ins will not be admitted. Register here. An event from the Friends of the Weston Library.
Wednesday October 28, 2026
Witches of Connecticut
10:00 am
Weston History & Culture Center
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.
Sunday November 8, 2026
Sunday Soundscapes
4:00 pm
Weston Public Library
Acclaimed pianist Anthony Ratinov performs, a preview of his upcoming recital at Carnegie Hall and the maiden voyage for the library’s beautiful new Estonia grand piano. Mr. Ratinov won raves at his previous Soundscapes appearance, a program of Beethoven and Haydn trios two years ago. Seating is limited, so it’s a good idea to make a reservation. Admission is free, but suggested donations of $20 for adults or $10 for students are more than welcome.
Wednesday November 11, 2026
Blood Drive
1:00 pm – 6:00 pm
St. Francis of Assisi Church
35 Norfield Road
An American Red Cross blood drive, with blood in short supply in Connecticut. Appointments are necessary. Make one by calling 1-800-RED CROSS (800-733-2767) or booking one online. Enter the zip code and scroll down to the November 11 drive.