2025 New Canaan Fall Fun Guide: Sunset Tours, Oktoberfest Celebration And More

NEW CANAAN, CT — The autumnal equinox on Monday, Sept. 22, signals the official arrival of fall, but the season is already in full swing in the New Canaan area with events such as corn mazes, hay rides, fall festivals and harvest events.

Sunny days and crisp evenings are perfect for outdoor fun. One can’t-miss event is are the sunset tours at The Glass House in New Canaan.

But that’s just the beginning of fun activities taking place over the next couple of months.

See also: Where To Pick Apples Around New Canaan: 2025 Guide

Are you planning an event this fall? Feature it so nearby readers see it all across Patch — including in roundups like this!

Below, find the 2025 Patch Guide to Fall Fun in the New Canaan area:

• Sunset Tours (New Canaan)

Enjoy a rare opportunity to explore The Glass House and its grounds at sunset. This special two-hour guided tour offers a golden-hour experience of the site and its many distinct architectural landmarks.

• The Waypointe Announces Oktoberfest 2025 Celebration (Norwalk)

The Waypointe is bringing the festive spirit of Germany to Fairfield County with an Oktoberfest 2025 celebration, happening Saturday, September 20th from 12 PM to 3 PM at the Waypointe Retail Courtyard, 515 West Avenue, Norwalk, CT.

• Norwalk Senior Center Flea Market & Book Fair (Norwalk)

The annual Norwalk Senior Center "Fabulous Flea Market" & AuthorPalooza sponsored by the Norwalk Public Library will take place on Saturday, September 27th from 9-4pm. The public is welcome.

• Oyster Festival on the Sound (Norwalk)

Hosted by the Westport Knights of Columbus. Fundraiser for Charitable Organizations. Copps Oysters, Clams, Jimmy’s Fried Clams, Burger Sliders, BBQ Pulled Pork, Beer,Wine and Dessert.

• Oktoberfest with the Norwalk Seaport Association (Norwalk)

Experience the spirit of Bavaria at our festive event, where camaraderie and community—what the Germans lovingly call “Geselligkeit”—take center stage at 314 Beer Garden and Wood-Fired Pizza.

• Connecticut 's Best HALLOWEEN Dance Party + Costume Contest (Norwalk)

Join us for Connecticut's Best Halloween Dance Party — only at Troupe429 in Norwalk, CT! FRIDAY, OCTOBER 31, 2025, hosted by Sienna Rose!

• Jazz Vespers--featuring Malin Carta! (Westport)

Get ready for an uplifting afternoon of live jazz, poetry, & prayer as The United Methodist Church of Westport & Weston (“UMC-WW”) located at 49 Weston Road, Westport, CT proudly presents Malin Carta, jazz saxophonist group.

• Pumpkin Paint Party (Darien)

Grab the kiddos and join us at Darien Commons on Sunday, October 5 from 12–3pm for our first-ever Pumpkin Paint Party!